19
IAOe?IIAEUeIA AEAAeAI?ss IAOE OE?A?IE
?INOEOOO A?II?AAI?*II? O?I?? OA IAOOIO?I??
OAAeI?ssE Ieany Aeieo??aia
OAeE 577.113.6:542.95
IIAeEO?EIAAI? EIIIIIAIOE IOEEA?IIAEO EENEIO:
NEIOAC ? AEANOEAINO?
02.00.10 – a?ii?aai?/ia o?i?y
Aaoi?aoa?ao aeena?oaoe?? ia caeiaoooy iaoeiaiai nooiaiy
eaiaeeaeaoa o?i?/ieo iaoe
Ee?a – 1999
Aeena?oaoe??th ? ?oeiien.
?iaioa aeeiiaia a ?inoeooo? a?ii?aai?/ii? o?i?? oa iaooio?i?? IAI
Oe?a?ie ? a Oi?aa?neoao? i. E?iiae (O?aioe?y).
Iaoeia? ea??aieee:
aeieoi? iaaee/ieo iaoe, i?ioani?
Eoee Ieaenaiae? ?ai?iae/,
?inoeooo a?ii?aai?/ii? o?i?? oa iaooio?i?? IAI Oe?a?ie,
caa?aeoaa/ a?aeae?eo iaaeeei-a?ieia?/ieo aeine?aeaeaiue
i?ioani? E?in I’?? (Krausz Pierre),
Oi?aa?neoao i. E?iiae (O?aioe?y),
ea??aiee eaai?aoi??? o?i?? i?e?iaeieo niieoe.
Io?oe?ei? iiiiaioe:
aeieoi? o?i?/ieo iaoe, i?ioani?
NA?AA?ssIEE Naoe Aaioe?iiiae/,
?inoeooo a?ii?aai?/ii? o?i?? oa iaooio?i?? IAI Oe?a?ie,
aieiaiee iaoeiaee ni?a?ia?oiee-eiinoeueoaio
eaiaeeaeao o?i?/ieo iaoe, noa?oee iaoeiaee ni?a?ia?oiee
AEAEN??AA ?iia Aieiaeeie??aia,
?inoeooo iieaeoey?ii? a?ieia?? oa aaiaoeee IAI Oe?a?ie,
noa?oee iaoeiaee ni?a?ia?oiee
I?ia?aeia onoaiiaa:
Ee?anueeee oi?aa?neoao ?iai? Oa?ana Oaa/aiea,
eaoaae?a i?aai?/ii? o?i??, I?iina?oe Oe?a?ie, i. Ee?a
Caoeno a?aeaoaeaoueny “ 2 ” ea?oiy 1999 ?. i 10-00 aiaeei? ia
can?aeaii? niaoe?ae?ciaaii? a/aii? ?aaee Ae 26.220.01 a ?inoeooo?
a?ii?aai?/ii? o?i?? oa iaooio?i?? IAI Oe?a?ie, 253660, Ee?a-94,
aoe.Io?iainueea, 1.
C aeena?oaoe??th iiaeia iciaeiieoenue o a?ae?ioaoe? ?inoeoooo
a?ii?aai?/ii? o?i?? oa iaooio?i?? IAI Oe?a?ie, 253660, Ee?a-94,
aoe.Io?iainueea, 1.
Aaoi?aoa?ao ?ic?neaiee “ 28 ” ethoiai 1999 ?.
A.i. a/aiiai nae?aoa?y
niaoe?ae?ciaaii? a/aii? ?aaee A.I.Eiaooi
CAAAEUeIA OA?AEOA?ENOEEA ?IAIOE
Aeooaeuei?noue oaie. Neioaoe/i? ie?aiioeeaioeaee ciaeoee oe?iea
canoinoaaiiy a iieaeoey?i?e a?ieia?? oa aaiaoe/i?e ?iaeaia???. Iniaeeai
caoe?eaaeai?noue aei ieo c?inea i?ney oiai, ye aoei iieacaii, ui
ie?aiioeeaioeaee iiaeooue i?eai?/oaaoe aeni?an?th a?aeiia?aeieo aai?a ?,
oaeei /eiii, iiaeooue aooe aeei?enoai? ye iiaee oei oa?aiaaoe/ieo
cania?a c iaaecae/aeii aenieith ao?ii?noth oa naeaeoeai?noth ae??.
I?ioa i?aeoe/ia aeei?enoaiiy i?e?iaeieo ie?aiioeeaioeae?a aeineoue
iaiaaeaia /a?ac ianoaa?euei?noue ?o eiiieaen?a c IE-i?oaiyie,
iano?ee?noue a i?enooiino? ee?oeiieo ioeeaac oa iecueeo caeaoi?noue
i?iieeaoe /a?ac ee?oeii? iaia?aie. Oea iaaeaei ?noioiiai iiooiaoo aei
neioaco ??ciei /eiii iiaeeo?eiaaieo ie?aiia??a c iaoith iiaeieaiiy
aeacaieo iaaeie?e?a.
Inoaii?i /anii neioaciaaia cia/ia e?euee?noue aiaeia?a ioeea?iiaeo
iniia, ioeeaiceae?a, ioeeaioeae?a oa ie?aiioeeaioeae?a, iiaeeo?eiaaieo
ii aaoa?ioeeee?/iiio, aoaeaaiaeiiio aai oinoaoiiio o?aaiaioao iieaeoe.
Ao?oeeaiai ?icaeoeo oeae iai?yiie iaaoa, o ia?oo /a?ao, caaaeyee
aeyaeaiith na?aae oeueiai eeano niieoe ?a/iaei c i?ioeiooeeiieie,
aioea??onieie oa ?ioiiiiaeoethth/eie aeanoeainoyie. Aeaye? c ieo oaea
oe?iei canoiniaothoueny a iaaee/i?e i?aeoeoe? aai i?ioiaeyoue ee?i?/i?
aei?iaoaaiiy.
Iiaeeo?eiaai? ie?aiioeeaioeaee ana oe?oa aeei?enoiaothoueny ye
AeIE-ciiaee, i?aeia?e aeey IE?, a aioenainia?e/aioeaaii?e oaoiieia??,
oiui. ?ic?iaea iaoiae?a iiaeeo?eaoe?? ie?aiioeeaioeae?a c iaoith
iaaeaiiy ?i oe?iieo aeanoeainoae (no?eeino? aei ioeeaac, iie?auaiiy
i?iieeiaiiy /a?ac ee?oeii? iaia?aie, iiaeeeaino? ia?aae?iaeoeaii?
aeaoaeoe?? oa ?i.) iaaoaa? ana a?eueoi? aeooaeueiino?.
Ca’ycie ?iaioe c iaoeiaeie i?ia?aiaie, ieaiaie, oaiaie. ?iaioa
aeeiioaaeanue a ?aieao Iaoe?iiaeueii? i?ia?aie “I?io?eaeoeea NI?Ae a
Oe?a?i?” ca oaiith “?ic?iaea iiaeo aoaeoeaieo iaoiae?a ae?aaiinoeee
NI?Ae, ui aacothoueny ia aeei?enoaii? ia?aae?iaeoeaieo
ie?aiioeeaioeaeieo i?oie” (0395U01037), iaoeiai-aeine?aeii? ?iaioe
“Noai?aiiy aeniei/ooeeaeo oano-nenoai aeey ae?aaiinoeee ? i?eai?/aiiy
aeeoo?caeaoiino? i?eiieaci, i?e/aoieo aei caoai?thaaiue NI?Ae, a oaeiae
?ani??aoi?iiai oa o?iaai?oaeueiiai o?aeo?a ethaeeie” (0194U005451) oa o
a?aeiia?aeiino? c ieaiaie ?ia?o eaai?aoi??? o?i?? i?e?iaeieo niieoe
Oi?aa?neoaoo i. E?iiae (O?aioe?y).
Iaoa ? caaea/? aeine?aeaeaiiy. Neioac iiaeeo?eiaaieo
ie?aiaeaciene?eaiioeeaioeae?a (eii’thaaoe?y c ?aii?oa?ieie niieoeaie,
iiaeeo?eaoe?y i?aeioeeaioeaeieo ca’yce?a, aaoa?ioeeee?/ieo iniia,
aaaaeaiiy a ie?aiia? iai?e?iaeieo aiaeia?a ioeeaiceae?a) oa
aeine?aeaeaiiy ?o aeanoeainoae.
Iniiai? caaea/? aeine?aeaeaiiy:
· Neioac oa aea/aiiy aeanoeainoae iiaeo iai?e?iaeieo aiaeia?a
ioeeaiceae?a;
· ?ic?iaea iaoiae?a iiaeeo?eaoe?? ie?aiioeeaioeae?a aaaaeaiiyi a
ie?aiia?iee eaioetha iai?e?iaeieo aiaeia?a ioeeaiceae?a;
· Noai?aiiy c?o/iiai ?aaaaioo aeey oeoi?anoeaioiiai i?/aiiy
ie?aiioeeaioeae?a;
· Neioac o?ioinoaoieo aiaeia?a ie?aiioeeaioeae?a – ?ia?a?oi??a i?ioean?a
o?aineyoe?? a ee?oeiao iie?eoo?a;
Iaoeiaa iiaecia iaea?aeaieo ?acoeueoao?a. ?ic?iaeai? iaoiaee neioaco
i??aceiiiiaeo ? oei?iiaeo aiaeia?a aoeeeeia??o, ?o aceaei- oa
ae?eiceeueiaaieo iio?aeieo.
Noai?aiee c?o/iee iaoiae iiaeeo?eaoe?? ie?aiioeeaioeae?a ioeeaiceaeiei
iio?aeiei ?i?aeacioaiaceio, i?e?aeiaiei aei 3’-e?ioey ie?aiia?o.
Iieacaii, ui i?e?aeiaiee oaeei niiniaii iaeo?aeueiee oaiacei ?noioii
i?aeaeuo? noaa?euei?noue eiiieaen?a c IE.
Iaea?aeaii aoaeoeaiee I-oinoiiaoiee ?aaaaio aeey i?yiiai
5’-oeoi?anoeaioiiai i?/aiiy ie?aiioeeaioeae?a a i?ioean? ?o neioaco.
Neioaciaaii ?yae o?ioinoaoieo aiaeia?a ie?aiaeaciene?eaiioeeaioeae?a,
eiiieaiaioa?ieo aei neaiaoo?ieo ae?eyiie 16S ??IE iie?eoo?a, ye?
aoaeoeaii ?ia?aothoue i?ioean o?aineyoe?? a ee?oeiao oeeo
i?e?ii?aai?ci?a.
I?aeoe/ia cia/aiiy iaea?aeaieo ?acoeueoao?a. Cai?iiiiiaaiee
oeoi?anoea?i-I-oinoiiao aeicaiey? io?eioaaoe oeoi?anoeaioii-i?/ai?
ie?aiioeeaioeaee a iaeio noaae?th a i?ioean? ?o neioaco a oaa?aeioaciiio
aa??aio?, aai a ?ic/ei?. Iaea?aeai? oeoi?anoeaioii-i?/ai? ie?aiia?e
c?o/i? aeey aeei?enoaiiy a iieaeoey?ii-a?ieia?/ieo aeine?aeaeaiiyo ? a
iaaeeoeei?, ye aeueoa?iaoeaa ?cioiiiei i?oeai.
O?ioinoaoi? aiaeiae ie?aiioeeaioeae?a, eiiieaiaioa?ieo aei neaiaoo?ieo
ae?eyiie 16S ??IE iie?eoo?a aeyaeeeny iaaecae/aeii aoaeoeaieie
?ia?a?oi?aie o?aineyoe??, no?eeeie aei ae?? ioeeaac. Aeniea
naeaeoeai?noue aioeneaiaoo?ieo ie?aiaeaciene?eaiioeeaioeae?a ?
ia?aaeoiiaith aeey oe?eani?yiiaaiiai noai?aiiy ia ?o iniia?
aioei?e?iaieo o?i?ioa?aiaaoe/ieo cania?a.
Iniaenoee aianie caeiaoaa/a. Aeena?oaio aaciina?aaeiuei aeeiioaaa on?
?iaioe ii o?i?/iiio neioaco oa o?ceei-o?i?/iiio aiae?co, naiino?eii
i?iaiaeea ocaaaeueiaiiy oa ?ioa?i?aoaoe?th io?eiaieo ?acoeueoao?a.
A?ieia?/i?, iaaeeei-a?ieia?/i? ? oeoi?anoeaioi? aeine?aeaeaiiy io?eiaieo
niieoe cae?eniai? o a?aeae?eao i?eiieaciieia?? ?inoeoooo i?e?ia?ieia??
oa a??onieia?? IAI Oe?a?ie, iieaeoey?ii? a?io?ceee O?ceei-oaoi?/iiai
?inoeoooo iecueeeo oaiia?aoo? IAI Oe?a?ie oa a ?inoeooo? a??onieia??
Oi?aa?neoaoo Eo? Ianoa?a (i. No?anao?a, O?aioe?y).
Ai?iaaoe?y ?acoeueoao?a aeena?oaoe??. Iaoa??aee aeena?oaoe?eii? ?iaioe
?icaeyioo? oa iaaiai?ai? ia Ia?oiio c`?cae? Oe?a?inueeiai a?io?ce/iiai
oiaa?enoaa (Ee?a, 1994), ia Ia?o?e Iaoe?iiaeuei?e iaoeiai-i?aeoe/i?e
eiioa?aioe?? c i?iaeai A?E/NI?Ae (Ee?a, 1995), ia XVI
Na?aaecaiiiii?nuee?e eiioa?aioe?? c oeoe??a (XVIemes Journees
Mediterraneennes des Glucides (L’Isle-sur-la-Sorgue, O?aioe?y, 1996), ia
eiioa?aioe?? “I?aai?/ia o?i?y: ca’ycie c a?io?i??th” (Journee “Chimie
Organique: Interface avec la Biochimie” (Poitiers, O?aioe?y, 1996).
?acoeueoaoe ie?aieo aoai?a ?iaioe aeiiia?aeaeenue ? iaaiai?thaaeenue ia
can?aeaiiyo a/aii? ?aaee oa iaoeiaeo nai?ia?ao a ?inoeooo? a?ii?aai?/ii?
o?i?? oa iaooio?i?? IAI Oe?a?ie, a eaai?aoi??? o?i?? i?e?iaeieo niieoe
Oi?aa?neoaoo i. E?iiae ? a eaai?aoi??? a?ii?aai?/ii? o?i?? Oi?aa?neoaoo
i. Ai?aei (O?aioe?y).
Ioae?eaoe??. Ca iaoa??aeaie aeena?oaoe?? iioae?eiaaii 8 i?aoeue, c ieo 4
noaoo? a iaoeiaeo oaoiaeo aeo?iaeao ? 4 oace eiioa?aioe?e oa c’?cae?a.
No?oeoo?a aeena?oaoe??. Aeena?oaoe?eia ?iaioa neeaaea?oueny c anooio,
iaeyaeo e?oa?aoo?e (1 ?icae?e, 2 i?ae?icae?ee), aenia?eiaioaeueii?
/anoeie (2 ?icae?ee, 9 i?ae?icae?e?a), aeniiae?a ? nieneo aeei?enoaieo
e?oa?aoo?ieo aeaea?ae (189 iaeiaioaaiue). ?iaioa aeeeaaeaia ia 123
noi??ieao iaoeiiieniiai oaenoo oa i?noeoue 57 ?ethno?aoe?e ? 23
oaaeeoe?.
INIIAIEE CI?NO AeENA?OAOe??
NEIOAC ? AEANOEAINO? IAI?E?IAeIEO AIAEIA?A IOEEAICEAe?A
C /ano a?aee?eooy 9-[2-(a?ae?ieneaoiene)iaoee]aoai?io (aoeeeeia??),
naeaeoeaiiai aioeaa?ianiiai aaaioo, cia/iee ?ioa?an aoa ni?yiiaaiee ia
neioac iiaeo aoeeee?/ieo aiaeia?a ioeeaiceae?a. A ?acoeueoao? oeeo
aeine?aeaeaiue aeyaeaii ?yae a?ae?ieneaee?eiaaieo iio?aeieo aoai?io c
aioea??onieie aeanoeainoyie. Iaaeaaii iieacaii, ui aeaye? 6-cai?uai?
aoeeee?/i? i??ei?aeeiia? ioeeaiceaee aeecuee? aei aoeeeeia??o,
iai?eeeaae, 1-[2-(a?ae?ieneaoiene)iaoee]-6-(oai?eo?i)oei?i (IA?O), ?
naeaeoeaieie ?ia?a?oi?aie A?E a ??cieo e?ioioeeoao ethaeeie.
A iao?e ?iaio? cae?eniaiee neioac iiaeo aiaeia?a aoeeeeia??o (iio?aeieo
i??aceio ? oei?io) oa o?ainoi?iaoe?y 4’-iieiaeaiiy a?ae?ieneaooeeueiiai
eaioethaa a?ae?ieneaee?eiaaieo ioeeaiceae?a aceaeoaaiiyi ?
ae?eiceethaaiiyi.
A?ae?ieneaooee- oa aceaeiaooeei??aceiiie
I?e?aeiaiiy aooeeueiiai eaioethaa aei i??aceiii?a 1a,b,c cae?enithaaee
ca noaiith, iaaaaeaiith ia ?en. 1. (?) Aei ioieiaeaeaiiai aei 0 0N
?ic/eio i??aceiiio a DMF aeiaeaaaee 1,2 aea. NaH, ia?ai?ooaaee 2 aiae ?,
i?e e?iiaoi?e oaiia?aoo??, aeiaeaaaee 1,2 aea. 4-a?iiaooeeaoeaoaoo.
*a?ac 16 aiae iaea?aeoaaee noi?o, ui neeaaeaeanue c i?iaeoeo?a (2) oa
(4), ye? ?icae?eyee o?iiaoia?ao??th ia eieiioe? c nee?eaaaeai. ?o
aeaoaeoe?y iieaaooaaeany caaaeyee oiio, ui N-cai?uai? niieoee
aani?aothoue i?e 254 ii oa oeoi?anoe?ththoue i?e 365 ii, oiae? ye
I-cai?uai? iio?aei? iicaaaeai? oeoi?anoeaioe??.
Aeai? ?*-niaeo??a aeicaieeee ?aeaioeo?eoaaoe i?noea i?e?aeiaiiy
aoeaoieneaee?eueiiai caeeoeo. I?iaeoeo 2a aea? nioao iiaeeiaiiy
= 1645 ni-1, ui a?aeiia?aea? eieeaaiiyi ea?aii?eo i??aceio. Oey nioaa
a?aenooiy o aeiaaeeo i?iaeoeoo 4a, aeey yeiai aeyaeaii iaeanoue
iiaeeiaiiy i?e 1220 ni-1 oa 1100 ni-1, ui a?aeiia?aea? aneiao?e/iei oa
neiao?e/iei eieeaaiiyi CAr-O-CAlk. Ia iaio niaeo?ao i?enooiy nioaa
= 1720 ni-1, ui a?aeiia?aea? aaeaioiei eieeaaiiyi ea?aii?eo
aoeaoeeueii? a?oie. Niieoee 2b,n oa 4b,n iathoue niaeo?e aiaeia?/i? aei
niieoe n?iaenoaa a. Aeey ian-niaeo??a oa?aeoa?i? ?ioaineaiee i?e
i?ioiiiaaiiai iieaeoey?iiai ?iio (I+I)+ oa i?ee, ui a?aeiia?aeathoue
o?aaiaioai c aeaeaeaieie OAc-a?oiaie oa aee?eueieie caeeoeaie.
A ?acoeueoao? aeaaeieoaaiiy 2a,b,n oa 4a,b,n 2 aea. iaoeeaoo iao??th
iaea?aeai? niieoee 3a,b,n oa 5a,b,n (?en. 1, ??). Aeoiaee 90-96 %.
wmetafile8? ??m5???????????yyy????x????
§???ue?????????-????????? ???? ???u?????????”????-?
???u??????????”????-????ue???????????-????u??????1/4???I
”System?I???-????
????-????-????-?????u?y???????en. 1
A?aeuaieaiiy aoeaoeeueii? a?oie i?aeoaa?aeaeaii iaoiaeaie ?*- oa
ssI?-niaeo?ineii??. Ia ?*-niaeo?ao ca?a?no?iaaii cieeiaiiy nioae
aaeaioiiai eieeaaiiy N=I aoeaoeeo ( = 1720 ni-1) ? iiyaa nioae a iaeano?
iiaeeiaiiy i?ae 3500 oa 3200 ni-1, ui a?aeiia?aea? eieeaaiiyi
a?ae?ieneeueii? a?oie. Ia 1I-ssI?-niaeo?ao niieoe 3a,b,n oa 5a,b,n
neaiaee i?ioii?a I aee?eueiiai eaioethaa cnoioo? a a?eueo neeueia iiea
(3,58-3,65 i.ae.), i?ae neaiaee ?aeaioe/ieo i?ioii?a aeo?aeieo
aoeaoeeueiaaieo i?iaeoeo?a (4,10-4,15 i.ae.).
Aceaeoaaiiy a?ae?ieneeueiaaieo niieoe (???) neeaaea?oueny c aeaio
aoai?a: i?e?aeiaiiy aei a?ae?ieneeo a?oie, ui eaaei aeaeaey?oueny
(iaea?eueo oe?iei aeei?enoiao?oueny oiceeueia a?oia), oa iiaeaeueoa
ioeeaio?eueia cai?uaiiy ?? ia aceaeia?oio.
Ni?iaa cae?enieoe oiceethaaiiy 1-(4-a?ae?ieneaooee)-2-i??aceiiio ca
iaoiaeii ?aii iaa?oue i?ioyaii 72 aiae ?aaeoe?? i?e e?iiaoi?e
oaiia?aoo?? aaaeaiiai i?iaeoeoo ia aeaea. I?aeaeuaiiy oaiia?aoo?e oaae
ia i?eaaei aei caaeia?eueiiai ?acoeueoaoo. Oiio oiceethaaiiy cai?ieee
iaceethaaiiyi, yea cae?enithaaee o aacaiaeiiio i??eaeei? a i?enooiino? 4
aea. iaceeoei?eaeo (MsCl, CH3-SO2-Cl).
Aeyaeeiny, ui iaceeueiaaiee i?iaeoeo ianoaa?eueiee iaa?oue i?e e?iiaoi?e
oaiia?aoo?? – /a?ac aiaeeio ?aaeoe?? iii?/aia eiai aeaa?aaeaoe?y
(aeieeiaiiy aaaaoueio ieyi ia OOO). Aaaeaiee i?iaeoeo ooai?thaaany eeoa
i?e 0 0N. Oiio io?eiaio noi?o aeei?enoiaoaaee a ?aaeoe?? aceaeoaaiiy aac
aeiaeaoeiai? i/enoee, yeo cae?enithaaee a DMF i?e 100 0N a i?enooiino? 5
aea. NaN3. *a?ac 1 aiae ?aaeoe?eio noi?o aeno?aaoaaee oei?ioi?iii ?
i/euaee i?aia?aoeaiith o?iiaoia?ao??th ia eieiioe? c nee?eaaaeai. I?e
oaeeo aea oiiaao aenia?eiaioo io?eiai? aceaee 2-I-cai?uaieo
(4-a?ae?ieneaooee)-2-i??aceiii?a 5a,b,n. Eiio?ieue ca oiaeii ?aaeoe??
cae?enithaaee ca aeiiiiiaith ?*-niaeo?ineii??: iiyaa ?ioaineaii? nioae
iiaeeiaiiy a iaeano? = 2110 ni-1 na?ae/eoue i?i i?e?aeiaiiy aceaeia?oie
aei aee?eueiiai eaioethaa. Oey nioaa i?enooiy a ?*-niaeo?ao on?o
neioaciaaieo aceaeiiio?aeieo. A ian-niaeo?ao 6a,b,n oa 7a,b,c iayai?
?ioaineai? i?ee i?ioiiiaaiiai iieaeoey?iiai ?iio II+. I?e aiae?c?
1I-ssI?-niaeo??a niieoe 6 ? 7 iii?/aii, ui aaaaeaiiy aceaeia?oie ia
aieeaa? ia aaee/eie o?i?/ieo cnoa?a i??aceiiaeo i?ioii?a oa i?ioii?a H,
I oa I aee?eueiiai eaioethaa. I?ioa aeey i?ioii?a I niinoa??aa?oueny
cnoa a a?eueo neeueia iiea ( 3,34-3,37 i.ae.), i?ae aeey ?aeaioe/ieo
i?ioii?a aeo?aeieo a?ae?ieneeueiaaieo i?iaeoeo?a ( 3,58-3,65 i.ae.). Oa
ae naia niinoa??aa?oueny ? i?e aiae?c? 13N-ssI?-niaeo??a: aeey neaiae?a
N iii?oiee cia/iee cnoa a iaeanoue neeueiiai iiey 50,8 i.ae. ii??aiyii
c 62,0-62,3 i.ae. aeey a?ae?ieneeueiaaieo ?a/iaei.
I??aceiiiia? ?eaiioeeaiceaee c iiaeeo?eiaaiei ae?eiceaeiei ca’yceii
Noai?aiiy iiaiai oeio aiaeia?a ioeeaiceae?a, ui i?noyoue niaena? i?ae
aaoa?ioeeee?/iith iniiaith oa oeoe?iaei caeeoeii –
N1-[4-(-D-?eaioo?aiiceeiene)-aooee]-3-aee?e-2-i??aceiii?a c a?oiaie I-,
NI3- aai N10I21- a 3-io iieiaeaii? iniiae, iiaea i?eaanoe aei
iaea?aeaiiy niieoe c oe?eaaeie a?ieia?/ieie aeanoeainoyie, /e
i?ea?iaeueieo iiaeeo?eiaaieo ie?aiioeeaioeae?a i?e aaaaeaii? ?o a
ie?aiia?iee eaioetha.
?aaeoe?th ae?eiceethaaiiy cae?enithaaee c aeei?enoaiiyi
1-I-aoeaoee-2,3,5-o?e-I-aaici?e–D-?eaioo?aiice oa nenoaie
SnCl4/aoeaoii?o?ee. ?aaeoe?? aaee i?e e?iiaoi?e oaiia?aoo?? a
aacaiaeiiio na?aaeiaeu? (?en. 2, iv).
wmetafile8? ??e ???????????yyy????Y y???
GTH???ue?????????-????????? ????
???u?????????”????-?
???u??????????”????-????ue???????????-????u??????1/4???I
”System?I???-????
????-????-????-?????u?y???????en. 2
Iiyaa a ?*-niaeo?ao oa?aeoa?ii? aeey ao???a nioae a?ey 1730 ni-1
na?ae/eoue i?i iayai?noue a iieaeoe? aaici?eueiaaiiai ae?eiceaeo.
Ian-niaeo?e eiaeii? ?c niieoe aeaiiino?othoue iayai?noue i?eo
i?ioiiiaaiiai iieaeoey?iiai ?iio [M+H]+. Ia 1I-ssI?-niaeo?ao (CDCl3)
?ioa?i?aoiaai? neaiaee, ui a?aeiia?aeathoue i?ioiiai iniiae, aooeeueiiai
eaioethaa oa aaici?eueiaaiiai oeoe?o. Aiiia?iee i?ioii ?aciio? o oi?i?
?icoe?aiiai neiaeaoo 5,23 i.ae. cai?noue cae/aeiiai aeoaeaoo o aeiaaeeo
ioeeaiceae?a. I?e aiae?c? 1I-ssI?-niaeo??a a iaea?aeaieo niieoeao
iii?/aia iayai?noue aeii?oee -aiiia?o (aeecueei 20 %), oiaoi oieeiooe
?aoeai?caoe?? a oiae? ?aaeoe?? ia aaeaeiny.
Aeaaaici?ethaaiiy ioeeaiceae?a 8a,b,n (ii) cae?enithaaee iaoeeaoii
iao??th ca iaoiaeii Oie? oa ni?a?. Ca aeaieie OOO /a?ac 2 aiae aanue
aeo?aeiee i?iaeoeo aoei aeaaeieiaaii. Ae?eiceaee 9a,b,n io?eioaaee c
aeoiaeaie 75-89 %. No?oeoo?o niieoe i?aeoaa?aeaeaii ?*-niaeo?aie
(cieeiaiiy nioae iiaeeiaiiy a?ey 1750 ni-1, ui a?aeiia?aea? ca aaeaioi?
eieeaaiiy N=I aaiciao?a), ian-niaeo?aie (iayaiee ?ioaineaiee i?e
i?ioiiiaaiiai iieaeoey?iiai ?iio [M+H]+), a oaeiae niaeo?aie aani?aoe??
OO (CH3OH) (i?enooi?e eeoa iaeei iaeneioi a?ey 318 ii, ui a?aeiia?aea?
i??aceiiiiaei aaoa?ioeeeeai; i?e aani?aoe?? aaici?eueieo a?oi a?ey
248 ii a?aenooi?e). I?ioiii? ssI?-niaeo?e (ND3ID) iieacothoue cieeiaiiy
i?e?a, ui a?aeiia?aeathoue i?ioiiai o?ueio aaici?eueieo a?oi. A
13N-ssI?-niaeo?ao ?ioa?i?aoiaaii neaiaee aoaeaoe?a iniiae, aee?eueiiai
eaioethaa oa aeaaaici?eueiaaii? ?eaice, i?e/iio aeey neaiae?a N-1 oa N-4
iii?oiee ?noioiee cnoa a iaeanoue neaaiai iiey, iiaeeeai, /a?ac
cieeiaiiy ai?cio?iiiiai aoaeoo aaici?eueieo a?oi ( = 2,2 oa 4,8
a?aeiia?aeii).
Neioac iiaeeo?eiaaieo iio?aeieo oei?io
Na?aae /enaeueiiai eeano iai?e?iaeieo aiaeia?a ioeeaiceae?a aaaeeeaa
i?noea caeiathoue iiaeeo?eiaai? iio?aei? oei?aeeio. Iaea?eueo a?aeii?
na?aae ieo AZT oa D4T, ui i?iyaeythoue cia/io aioea??onio aeoeai?noue.
C iaoith iaea?aeaiiy iiaeo iio?aeieo oeueiai ioeeaiceaeo ie neioacoaaee
a?ae?ieneaooeeuei? oa iiaeeo?eiaai? ii ae?eiceaeiiio ca’yceo eiai
aiaeiae.
A?ae?ieneaooeethaaiiy cae?enithaaee o a?aeiia?aeiino? c? noaiith,
iaaaaeaiith ia ?en. 3, (i). Aei ?ic/eio oei?io a na?aeiia?aaiaiiio DMF
aeiaeaaaee 1,5 aea. a?ae?eaeo iao??th, noi?o o?eiaee i?e 100 N 4 aiae,
ioieiaeaeoaaee aei e?iiaoii? oaiia?aoo?e oa aeiaeaaaee 1,1 aea.
4-a?iiaooeeaoeaoaoo. ?ic/ei caeeoaee ia 2 aiae i?e e?iiaoi?e
oaiia?aoo??, i?ney /iai i?ae?a??aaee aei 100 N ? o?eiaee i?e oe?e
oaiia?aoo?? ua 7 aiae. Iaea?aeoaaee noi?o o?ueio niieoe, ye? eaaei
?icae?eyeenue o?iiaoia?ao??th ia eieiioe?: N1-aee?eiaaiee (10) ?
N1,N3-ae?aee?eiaaiee (11) i?iaeoeoe c aeoiaeaie 15 % oa 24 %
a?aeiia?aeii, oa 3 % I-aee?eiaaii? (12) iio?aeii?. ?o eaaei
?aeaioeo?eoaaoe ca aeiiiiiaith ssI?-niaeo?iiao??? (i?ioiie iniiae
?aciiothoue o ??cieo oi?iao – I-1 ia? aeaeyae aeoaeaoo, I-3 – neiaeaoo).
Anoaiiaeaii, ui iioeiaeueiiai aeoiaeo iiiicai?uaii? niieoee 10 (55 %)
i?e caaaeueiiio aeoiae? 89 % iiaeia aeinyaoe i?e aeei?enoaii? iaaeeeoeo
aee?eoth/iai ?aaaaioo. Oea i?ioe??/eoue ?ai?oa iioae?eiaaiei
?acoeueoaoai, a yeeo i?aeaeuaiiy aeoiaeo iiiiaee?eiaaiiai i?iaeoeoo
caaaeaee aeinyaaee i?e aeei?enoaii? noao?iiao?e/ieo e?eueeinoae
?aaaaio?a, aai iaaeeeoeo iniiae.
wmetafile8? ??„^???????????yyy????YO???
:?Z????ue?????????-????????? ???? ???u?????????”????-?
???u??????????”????-????ue???????????-????u??????1/4???I
”System?I???-????
????-????-????-?????u?y???????en. 3
C iaoith iaea?aeaiiy aeeae?eiceaeiiai iio?aeiiai oei?io niieoeo 11
aeacaoeaoeethaaee 1,5 aea. iaoeeaoo iao??th (?en. 3, ii). A?aeuaieaiiy
iaio aoeaoeeueieo a?oi i?aeoaa?aeeee iaoiaeaie ?*-niaeo?iiao???
(cieeiaiiy nioae aaeaioiiai eieeaaiiy N=I aoeaoeeo i?e = 1720 ni-1) oa
i?ioiiii? ssI?-niaeo?iiao??? (ci?uaiiy neaiae?a i?ioii?a I a iaeanoue
a?eueo neeueiiai iiey a?ae 4,09 oa 4,07 aei 3,67 i.ae.).
Niieoeo 13 ae?eiceethaaee ca ?ic?iaeaiei aeey i??aceiii?a iaoiaeii.
Ae?aee?eiaaia iio?aeia ?ic/eiyee a na?aeiia?aaiaiiio aoeaoii?o?ee?,
aeiaeaaaee 2,2 aea. 1-I-aoeaoee-2,3,5-o?e-I-aaici?e–D-?eaioo?aiice oa
oaeo ae e?euee?noue SnCl4. ?aaeoe?th aaee a aoiinoa?? a?aiio i?ioyaii 3
aiae. Iaea?aeaio noi?o ?icae?eyee o?iiaoia?ao??th ia eieiioe?. Aeo?ae
i?iaeoeoo 14 – 64 %. I?i i?iaaaeaia ae?eiceethaaiiy na?ae/eoue
iayai?noue ia 1I-ssI?-niaeo?? neaiae?a aaici?eueiaaiiai oeoe?o.
A?aeiioaiiy ?ioaa?aeueieo ?ioaineaiinoae neaiae?a i?ioii?a aoaeaaiae?a,
aaici?eueieo a?oi oa iniiae i?aeoaa?aeaeo? iayai?noue a iieaeoe? aeaio
ae?eiceaeieo caeeoe?a.
I?ney ia?iaee 14 iaoeeaoii iao??th i?ioyaii 4 aiae, iaeo?ae?caoe?? oa
aeno?aeoe?? c ianooiiei oia?thaaiiyi aiaeii? oace io?eioaaee 82 %
oe?eueiaiai i?iaeoeoo 15.
Ioaea, a ?acoeueoao? i?iaaaeaiiai aeine?aeaeaiiy ?ic?iaeai? iaoiaee
neioaco aoeeee?/ieo ioeeaiceae?a – i??aceiiiiaeo ? oei?iiaeo aiaeia?a
aoeeeeia??o oa ?o aceaei- ? ae?eiceaeieo iio?aeieo: N1- oa
2-I-(4-a?ae?ieneaooee)-, N1- oa 2-I-(4-aceaeiaooee)-,
N1-[4-(-D-?eaioo?aiiceeiene)-aooee]-3-aee?e-2-i??aceiii?a,
N1,N3-aee-(4-a?ae?ieneaooee)oei?io oa
N1,N3-aee-[4-(-D-?eaioo?aiiceeiene)-aooee]oei?io.
Neioaciaaii oa aeine?aeaeaii ?*-, ian-, 1I oa 13N ssI?-niaeo?e 30 iiaeo
niieoe.
A?eueo?noue io?eiaieo niieoe ia?aa??aia ia ?o in vitro ?ia?aoth/o ae?th
ia ?aie?eaoe?th ?yaeo a??onieo AeIE (i?inoiai a??ono aa?iano oeio 1,
oeeoiiaaaeia??ono ethaeeie, a??ono aaeoeeie) oa a??onieo ?IE (a??on
Coxsackie B4).
Niieoee, ui i?noyoue a?ae?ieneaooeeuei? caeeoee, ia aeyaeee ?noioii?
i?ioea??onii? aeoeaiino?. Iiaeeo?eaoe?y 4’-iieiaeaiiy a?ae?ieneeueii?
a?oie aceaeoaaiiyi (6a,b,c oa 7a,b,c) /e ae?eiceethaaiiyi (9a,b,c) ia
iie?aueea ?o aeanoeainoae.
I?e i?iaaaeaii? aeaio i?ia ia aioe-A?E 1 aeoeai?noue aeiaeia c
aeine?aeaeaieo niieoe ia aeyaeea aioea??oniiai aoaeoo a eiioeaio?aoe?yo,
ieae/eo a?ae i?i?iaeueii? eiioeaio?aoe??, yea aeeeeea? iii?oi? ci?ie
aeeoo?caeaoiino? ee?oei MT-4 ? CEM oacy?ia.
NEIOAC ? AEANOEAINO? 5’-, 3’-EII’THAAO?A OA O?IOINOAOIEO AIAEIA?A
IE?AIAeACIENE?EAIIOEEAIOEAe?A
Iiaeeoieiaaii ie?aiioeeaioeaee, yei iinoyoue eiaaeaioii i?e?aeiaii
caeeoee iioeo iieaeoe (oeoi?ioi?e, ?ioa?eaeyoi?e, aiaeiae ioeeaiceae?a,
eiiioieuei? iieaeoee oa ii.), oe?iei canoiniaothoueny a
iieaeoey?ii-aiieiai/ieo ? iaaee/ieo aeineiaeaeaiiyo oa a aiioaoiieiai?.
Cia/iee ?ioa?an aeeeeeathoue o?ioinoaoi? aiaeiae ie?aiioeeaioeae?a
caaaeyee ?o no?eeino? aei ae?? ioeeaac. O ca’yceo c oeei ?ic?iaea iiaeo
iaoiae?a 5’- oa 3’-iiaeeo?eaoe?? ie?aiia??a, aeecaei oa neioac
o?ioinoaoieo aiaeia?a iathoue aaaeeeaa oai?aoe/ia ? i?aeoe/ia cia/aiiy.
Neioac ? aeanoeaino? ieiaiioeeaioeaeia, iiaeeoieiaaieo ioeeaiceaeii
iiiaeacioaiaceio
I?e?aeiaiiy ?ioa?eaeyoi??a (ae?eaeei, aio?aoiiii, oaiaio?ieii, oaiacei
oa ii.) aei neioaoe/ieo ie?aiioeeaioeae?a cia/ii iiaeaeuo?
noaaieueiinoue aeai- oa o?eni??aeueieo eiiieaen?a oaeeo ie?aiia??a c
eiiieaiaioa?ieie iineiaeiaiinoyie IE, a ?acoeueoaoi /iai c?inoa?
aoaeoeaiinoue aca?iiaei? ie?aiioeeaioeaeo c eiai iioaiith aac iiiioii?
ao?aoe niaoeeoi/iinoi, ui iniaeeai aaaeeeai aeey iiaiaoaaiiy aeni?an??
aaiia. Iniaeeaee iioa?an noaiiaeyoue aiaeiae ioeeaiceae?a, ui iinoyoue
caeeoee iioa?eaeyoi??a ye aaeieiie. Oaei ioeeaiceaee iiaeia aaiaeeoe a
caaeaii iieiaeaiiy ieiaiioeeaioeaeii? iineiaeiaiino? aaciina?aaeiuei a
i?ioeani ?? oiii/iiai neioaco.
A iao?e ?iaio? aeei?enoaiee aiaeia ioeeaiceae?a – N1-?eaiceae
iiiaeaci[4,5-b]oaiaceio (Pzn), iaea?aeaiee nee?eueiith eiiaeainaoe??th
aaoa?ioeeeeo c ia?aoeeeueiaaiith ?eaicith. ?aiioa
niaeo?aeueii-oeoi?anoeaioieie aeineiaeaeaiiyie iieacaii, ui iioiaeii
iiiaeacioaiaceio aca?iiaeithoue c ioeea?iiaeie eeneioaie ca iaoaiiciii
iioa?eaeyoei?, noaaieicoth/e iieiioeeaioeaeii aeoieaene.
Aeey neioaco ieiaiioeeaioeaeieo iineiaeiaiinoae, ui iinoyoue aiiiaeueiee
ioeeaiceae ia 3′-eiioei, io?eiaii iieiia?iee iinie c ?iiia?e?ciaaiei Pzn
(?en. 4, 1) i?e?aeiaiiyi eiai o?eoie?eiaoeeueiiai iio?aeiiai aei
ai?iii?ii?eueiaaiiai nee?eaaaeth “Neeio?ii N-80″ /a?ac noeoeeiaoio
e?iea?io a?oio ca aeiiiiiaith iaoiae?a, cae/aeieo aeey io?eiaiiy
ioeeaiceaeai?nieo iie?ia??a. I?e oeueiio ooai?th?oueny neeaaeiiaoi?iee
ca’ycie iiae NIII-a?oiith iieiia?o oa 2′- aai 3′-aiae?ieneeii
ioeeaiceaeo, oiaoi, iieiia? iinoeoue ioeeaiceaeii caeeoee, eiaaeaioii
ca’ycaii ii aeaio iieiaeaiiyo. Oea ia aieeaa? ia iaea?aeaiiy
ieiaiioeeaioeaeieo i?iaeoeoia, ineieueee iiney aiaeuaieaiiy ieiaiia?o c
iiniy a iaio aeiaaeeao ooai?th?oueny ieiaiioeeaioeae c 3′-eiioeaaei Pzn.
3′(2′)-Aiae?ieneeueii a?oie ?iiia?e?ciaaieo ioeeaiceae?a aeieoaaee
aoeeethaaiiyi ioeoiaei aiaiae?eaeii a ii?eaeeii.
Neioac i?e?iaeieo oa iiaeeo?eiaaieo (?en. 4) ie?aiioeeaioeae?a
cae?enithaaee noaiaea?oiei I-oinoiiaoiei oaa?aeioaciei iaoiaeii ye a
aaoiiaoe/iiio, oae i a ?o/iiio aa?iaioi. Na?aaeiie aeoiae ?aaeoeie
eiiaeainaoei? noaiiaea 96-97 % ia noaaeith.
wmetafile8? ??^Z???????????yyy????‚M???
a6????ue?????????-????????? ???? ???u?????????”????-?
???u??????????”????-????ue???????????-????u??????1/4???I
”System?I???-????
????-????-????-?????u?y???????en. 4
Iiney caaa?oaiiy ia?iuoaaiiy ieiaiioeeaioeaeiiai eaioethaa oa ieeneaiiy
aiae?ioinoi?eeueieo a?oi ieiaiioeeaioeaee aiaeae?eyee a?ae iieiia?iiai
iiniy oa aeaaeieoaaee, ia?iaeyth/e eiioeaio?iaaiei NH3 i?ioyaii ii/?
(i?e e?iiaoi?e oaiia?aoo?? aeey ie?aioei?aeeeaoo oa i?e 50 0C aeey
(dA)15), a oeieueiai i?iaeoeoe i/euaee i?aia?aoeaiei
aaeue-aeaeo?ioi?acii. Ieiaiioeeaioeae, a neeaaei yeiai ciaoiaeeoueny
ioeeaiceae iiiaeacioaiaceio, eaaei aeyaeoe a aaei i?e OO-ii?iiiiaiii o
aeaeyaei /ioei? nioae c aeiaoith oeoi?anoeaioei?th.
Aeineiaeaeaii oiceei-oiii/ii aeanoeainoi neioaciaaieo ieiaiioeeaioeaeieo
iineiaeiaiinoae. A ?oiio aeaeo?iiieo niaeo?ao iiaeeiaiiy ii?o/ c
OO-iiaeeiaiiyi ieiaiioeeaioeaeo oa iiiaeacioaiaceio i?e 260-270 ii
?a?no?o?oueny nioaa aaeni?aoei? aa?aieea o aeaeeiie iaeanoi
(375-385 ii). I?e oeueiio niiaaiaeiioaiiy iioaineaiinoae iiaeeiaiiy
iiaeeoieiaaieo iineiaeiaiinoae a OO- i aeaeeiie iaeanoi ciaoiaeeeenue o
aiaeiiaiaeiinoi c ?ic?aoiaaieie ca eiaoioei?ioaie aenoeieoei?
iioa?eaeyoi?a oa ieiaiioeeaioeaeo. Iieacaii, ui aaaaeaiiy
3′-oa?iiiaeueiiai ioeeaiceaeo iiiaeacioaiaceio a aeaeaoeiiaeeeao (dT)10
caieueooaaei oaiia?aoo?o ieaaeaiiy eiai aeoieaenia c poly-A aai (dA)15
ia 10-12 0N ?, ua aieueoa (ia 15-20 0N), noaaieicoaaei iio?ieii
eiiieaene iiaeeoieiaaiiai (dT)10. Niaeo?ineiii/ii aeineiaeaeaiiy
aca?iiaei? c AeIE iieacaee, ui iniiaiei oeiii ca’ycoaaiiy iaeo?aeueiiai
o?iiioi?a iiiaeacioaiaceio ? iioa?eaeyoeiy aa?aieea, oiaei ye o aeiaaeeo
/aoaa?oeiieo nieae oaiaceiith cia/iee aeeaae a ooai?aiiy eiiieaenia
aiinyoue oaeiae aeaeo?inoaoe/ii aca?iiaei? c oinoaoieie a?oiaie. Ia iaoo
aeoieo, a inoaiiueiio aeiaaeeo cieaeo?oueny niaoeeoi/iinoue aiiciaaaiiy
iineiaeiaiinoae-iioaiae iiaeeoieiaaieie ieiaiioeeaioeaeaie ii?iaiyii c
ieiaiia?aie, ui iinoyoue iaeo?aeueiee iiiaeacioaiacei. I?e oeueiio
noaaieicoth/ee aieea iaeo?aeueieo oa eaoiiiieo iioa?eaeyoi??a
oaiaceiiaiai ?yaeo ia eiiieaiaioa?ii eiiieaene i?aeoe/ii iaeiaeiaee.
Ioaea, ?ic?iaeaii c?o/iee iaoiae neioaco ieiaiioeeaioeae?a,
iiaeeoieiaaieo ?eaiioeeaiceaeii iiiaeaci[4,5-b]oaiaceio a 3’-iieiaeaii?.
Iieacaii, ui oeae ioeeaiceae ye aoaeoeaiee iioa?eaeyoi? a neeaaei
iiaeeoieiaaieo ieiaiioeeaioeae?a ?noioii iineeth? noaaieuei?noue
eiiieaen?a c eiiieaiaioa?ieie IE oa iiaeaeuo? noieeinoue ie?aiia??a aei
aei? eeioeiieo ioeeaac. Eiiai?ii, ui caaaeyee nai?i eiiioieueiei
aeanoeainoyi a?i caeaoiee iie?aueoe o?ainii?o aioenainiaeo
ieiaiioeeaioeae?a a eeioeio. Ne?ae cacia/eoe, ui iioaineaia
oeoi?anoeaioeiy oeueiai o?iiioi?a (iaeneioi aiini? aa?aieea a neeaaei
ieiaiioeeaioeae?a niinoa?iaa?oueny i?e 537-539 ii) ?iaeoue eiai c?o/iith
?aii?oa?iith a?oiith aeey aeaoaeoei? IE oa aeey aea/aiiy i?ioeania
eiiieaeniooai?aiiy.
Oeoi?anoea?iiaee ?aaaaio aeey oaa?aeioaciiai 5`-i?/aiiy
ie?aiioeeaioeae?a
Oeoi?anoeaioi? aa?aieee ye ? ?io? ?aii?oa?i? iieaeoee iiaeooue aooe
eiaaeaioii i?e?aeiai? aei ie?aiioeeaioeaeo ??cieie iaoiaeaie. Cae/aeii
i?/aiiy ie?aiioeeaioeae?a cae?enith?oueny iino-neioaoe/ieie
i?ioeaaeo?aie. I?ioa ?aaeoe?eia noi?o, ui i?e oeueiio ooai?th?oueny,
i?noeoue aeo?aeiee ie?aiioeeaioeae ?acii c i?/aiei i?iaeoeoii, yeee
iaiao?aeii ?icae?eyoe ca aeiiiiiaith AA?O, a?eueoa oiai, aeaeaeaiiy
iaaeeeoeo aa?aieea iiaea noai?thaaoe na?eici? i?iaeaie. Ia iao iiaeyae,
i?yia i?/aiiy a i?ioean? o?i?/iiai neioaco a?eueo ia?niaeoeaia. I?e
oaeiio i?aeoiae? a?aeiia?aeiee ?aaaaio i?e?aeiothoue aei 5`-e?ioey
caoeuaiiai ie?aiia?a aaciina?aaeiuei i?ae /an eiai oaa?aeioaciiai
neioaco a oiiaao ?aaeoe?? i?aeioeeaioeaeii? eiiaeainaoe??. Oea iiaeeeaa
o oiio aeiaaeeo, eiee ?aii?oa?ia iieaeoea ia?aoai?aia a oinoai?aeia,
I-oinoiiaoia /e oinoiae?ao??ia (a caeaaeiino? a?ae ia?aiiai iaoiaeo
neioaco) iio?aeia, no?eea ia noaae?yo eiiaeainaoe?e oa aeaaeieoaaiiy.
Aeey neioaco ie?aiioeeaioeae?a iaie ia?aii I-oinoiiaoiee iaoiae, yeee
a?aecia/a?oueny i?inoioith, aenieith oaeaee?noth oa aoaeoeai?noth.
Iaoiae aaco?oueny ia eiiaeainaoe?? ioeeaiceae-I-oinoiiao?a c
ioeeaiceaeieie eiiiiiaioaie ia iie?ia?iiio iin?? a i?enooiino?
eiiaeainoth/iai ?aaaaioo, ye i?aaeei, i?aaei?eoei?eaeo (?en. 5).
Oinoaocaoeni? a?oie a oeueiio i?aeoiae? ia aeei?enoiaothoueny, a i?ney
caaa?oaiiy ia?iuoaaiiy ie?aiioeeaioeaeiiai eaioethaa an? I-oinoiiaoi?
ae?ao??e ieeneththoue iaeii?aciai.
wmetafile8? ??2-???%????????yyy????6!???
y6????ue?????????-????????? ???? ???u?????????”????-?
???u??????????”????-????ue???????????-????u??????1/4???I
”System?I???-????
????-????-????-?????u?y???????en. 5
I?e aeai?? oeoi?anoeaioiiai aa?aieea ie aeoiaeeee c oiai, ui aeey
aeinyaiaiiy iaeneiaeueii? /ooeeaino? oeoi?anoeaioia i?oea iiaeiia iaoe
iaeii/anii ye iioaineaia iiaeeiaiiy, oae ? aenieee eaaioiaee aeo?ae
oeoi?anoeaioe??. Na?aae aeine?aeaeaieo aa?aiee?a iaeiei c iaea?eueo
iioeiaeueieo aeyaeany oeoi?anoea?i (????????????eaaioiaee aeo?ae aei
90 %).
Aeey aeei?enoaiiy oeoi?anoea?io a oeueiio iaoiae? neioaco eiai aoei
io?eiaii o aeaeyae? I-oinoiiaoiiai ?aaaaioo ca ?ic?iaeaiith iaie
iaoiaeeeith (?en. 6). A ?acoeueoao? aoa?eo?eaoe?? oeoi?anoea?io
iaoaiieii a i?enooiino? H2SO4 io?eioaaee eiai iaoeeiaee ao?? (1). Aeey
aaaaeaiiy e?iea?ii? a?oie oaiieueiee a?ae?ienee aee?eoaaee
(4,4’-aeeiaoieneo?eoee)-4-oei?aooaiieii-1 a DMF a i?enooiino? K2CO3 ? KI
ye eaoae?caoi?a. I-Caoeuaiee 4-oei?aooaiie-1 eaaei io?eiaoe
o?eoeethaaiiyi nie?oo a i??eaeei?. I?ii?aeiee i?iaeoeo (2a)
aeao?eoeethaaee ? io?eiaiee iaoeeiaee ao??
6-(4-a?ae?ieneaooee)oeoi?anoea?io (3a) oinoi?eethaaee PTri3. ?aaeoe?th
aaee a noi?o? aoeaoii?o?ee-i??eaeei o ca`yceo c iecueeith ?ic/eii?noth
(3a) a aoeaoii?o?ee?. I-oinoiiao (4a) aeae?eyee ia eieiioe? c
nee?eaaaeai. Niieoee (1)-(4) ioa?aeoa?eciaai? ca aeiiiiiaith aeaiaioiiai
aiae?co oa niaeo??a oeoi?anoeaioe??.
wmetafile8? ??¬8?? ?????????&?
?yyyy????Word?Microsoft Word??????????”
???u?????????????I???Courier
New?I????-?????????uy???????en. 6
Oeoi?anoea?i-I-oinoiiao (4a) aeei?enoaee i?e iaea?aeaii?
5’-oeoi?anoea?ii?/aieo ie?aiioeeaioeaeieo i?aeia??a aeey aiie?o?eaoe??
ae?eyiie LTR oa env aaiiio HIV-1:
SK-29 5`-ACT AGG GAA CCC ACT GCT -3` (18)
SK-30 5`-GGT CTG AGG GAT CTC TA -3` (17)
SK-68 5`-AGC AGC AGG AAG CAC TAT GC-3` (20)
SK-69 5`-CCA GAC TGT GAG TTG CAA CAG-3` (21)
O?i?/iee neioac ie?aiioeeaioeae?a cae?enithaaee oaa?aeioaciei
I-oinoiiaoiei iaoiaeii c na?aaei?ie aeoiaeaie 98-98,5 % ia noaae?th.
I?ney i?e?aeiaiiy inoaiiueiai ioeeaioeaeo ? aeao?eoeethaaiiy
aaciina?aaeiuei ia iie?ia?? aaiaeeee oeoi?anoeaioio i?oeo ca aeiiiiiaith
oeoi?anoea?i-I-oinoiiaoo (4a). Eiiaeainaoe?th cae?enithaaee ?o/iei
iaoiaeii a noaiaea?oieo oiiaao, ye ? o aeiaaeeo ioeeaiceae-I-oinoiiao?a,
ca aeiyoeii aeiaoiai /ano eiiaeainaoe?? (4-5 oa.). Aeoiaee ia oe?e
noaae?? i?aeoe/ii e?euee?ni?.
I?iaaaeai? aeine?aeaeaiiy niaeo?aeueii-oeoi?anoeaioieo aeanoeainoae
iaea?aeaieo niieoe. Aeey ieo a OO-niaeo?? oa?aeoa?i? 2 iaeneioie
iiaeeiaiiy ?max: 260 ii ? 454 ii. Iiaeeiaiiy i?/aieo i?aeia??a i?e 260
ii coiiaeai? a iniiaiiio ie?aiioeeaioeaeiith /anoeiith, a a aeaeei?e
iaeano? (454 ii) – aeeeth/ii aa?aieeii. I?e aeae?eaii? Flu-i?/aieo
i?aeia??a aeaeo?ioi?acii o IAAA aiie aeia?a aeaei? ye nioae ?c
aeiaoi-caeaiith oeoi?anoeaioe??th a ?aeii? 510 ii. Aeaeo?ioi?aoe/ia
?ooeea?noue i?/aiiai ie?aiioeeaioeaeo caaaeyee iayaiino? aeiaeaoeiaiai
oinoiae?ao??iiai ca`yceo ieae/a, i?ae iai?/aiiai o??? ae iine?aeiaiino?.
Oea aeicaiey? aoaeoeaii a?aeae?eeoe aeo?aeiee ie?aiioeeaioeae a?ae
i?/aiiai i?iaeoeoo. I?e iaa?iaii-oacia?e o?iiaoia?ao?? i?/aiee
ie?aiioeeaioeae oa?aeoa?eco?oueny a?eueoei /anii oo?eiaiiy. E?euee?noue
oeoi?anoea?i-i?/aiiai ie?aiioeeaioeaeo, ui iiaea aooe cao?eniaaiee
iaica?i?iei ieii o aeaeyae? ieyie ia o?eueo?oaaeueiiio iaia??, neeaaea?
1-5 iiieue.
Oaeei /eiii, aeei?enoaiiy neioaciaaiiai iaie oeoi?anoea?iiaiai ?aaaaioo
(4a) aeicaiey? aoaeoeaii aaiaeeoe oeoi?anoeaioio i?oeo a ioeeaiceaee ?
ie?aiioeeaioeaee. A?i iiaea aooe aeei?enoaiee a oaa?aeioaciiio iaoiae?
neioaco ie?aiioeeaioeae?a ca noaiaea?oiith i?ioeaaeo?ith neioaco,
aeaaeieoaaiiy oa i/enoee, cia/ii ni?iuoth/e i?ioean iaea?aeaiiy
oeoi?anoeaioii-i?/aieo ie?aiia??a.
Aioeneaiaoo?i? ie?aiioeeaioeaee – iia? aioei?e?iai? caniae
C?inoaiiy no?eeino? i?e?ii?aai?ci?a aei ?nioth/eo i?aia?ao?a noaei
ia?aaeoiiaith iiooeo aeueoa?iaoeaieo aioei?e?iaieo cania?a, ye? ca
iaoai?ciii ae?? a?ae??ciythoueny a?ae aioea?ioee?a. A?aeiia?aei?
aeine?aeaeaiiy, ?icii/ao? a 1978 ?ioe?, aoee ni?yiiaai? ia noai?aiiy
ie?aiioeeaioeae?a, eiiieaiaioa?ieo aei niaoeeo?/ieo ae?eyiie IE-i?oaiae,
ye? aeieoaaee a i?ioeane ?aie?eaoe?? ? o?aine?eioe?? aaiiiii? AeIE aai
oiaiiaeeeaethaaee o?aineyoe?th ia ?eainiiao aaea o?aine?eaiaaieo c AeIE
?ioi?iaoe?eieo ?IE (??IE). I?ioa aieea ie?aiioeeaioeae?a ia oae? i?oai?
c oa?aiaaoe/ii? oi/ee ci?o aeyaeany c oeo /e ?ioeo i?e/ei iaaeinoaoiuei
aoaeoeaiei. ?noioiei iaaeie?eii aioenainiaeo ie?aiioeeaioeae?a ?
iaiao?aei?noue ?ia?aoaaiiy eiaeii? iiaineioaciaaii? ??IE, ui ??cei
i?aeaeuo? aeo?aoe oeeo ?aaaaio?a, eiioeaio?aoe?y yeeo iiaeiia nyaaoe 50
? a?eueoa ieiieue/e, uia noaoe caoaiith aeey i?e?iao, ui noa? oiene/iei
? aeey iae?ii?aai?cio.
Iica oaaaith aeine?aeiee?a caeeoeeeny iiaineioaciaai? (ua ia aeeth/ai?
a ?eainiie) ??IE ye i?oai? aeey ae?? ia ieo eiiieaiaioa?ieie
ie?aiioeeaioeaeaie c iaoith aeeeth/aiiy ?eainii c i?ioeano o?aineyoe??.
A ??IE, iniaeeai a 16S ??IE, aeyaeai? iine?aeiaiino?, oi?eaeuei? aeey
ie?aieo aeae?a i?e?ii?aai?ci?a. Aeei?enoiaoth/e oe? iine?aeiaiino? ye
i?oai? iiaeia i?eai?/oaaoe aeeoo?ae?yeuei?noue ie?aieo aeae?a iaoiaaiieo
i?e?ii?aai?ci?a.
Ia?aa??ea oe??? a?iioace cae?enithaaeany ia iaoiaaiieo i?eiieaciao (eean
Mollicutes). I?oaiyie aeey ae?? ie?aiioeeaioeae?a ia?aii niaoeeo?/i?
(“neaiaoo?i?”) iine?aeiaiino? ioeeaioeae?a 16S ??IE iie?eoo?a: 1)
5`-CUAACUAUG-3` – (iine?aeiai?noue 499-507) oa 2) 5`-UAAUACAUAG-3` –
(523-532).
Iaie neioaciaaii i?e?iaei? oa iiaeeo?eiaai? ii i?aeioeeaioeaeieo
ca’yceao ie?aiaeaciene?eaiioeeaioeaee, eiiieaiaioa?i? (“aioeneaiaoo?i?”)
aei oeeo iine?aeiaiinoae, a oaeiae o?ioinoi?eeueiaai? ie?aiioeeaioeaee c
ia?aeaeueieie iine?aeiaiinoyie (Oaaeeoey 1).
Neioac cae?enithaaee oaa?aeioaciei I-oinoiiaoiei iaoiaeii (?en. 5). I?e
iaea?aeaii? oiioinoaoieo aiaeia?a ieiaiioeeaioeaeia ia caeeth/iie
noaaei? neioaco aiae?ioinoi?eeuei? a?oie ieiaiioeeaioeaeiiai eaioethaa
ieenethaaee aaciina?aaeiuei ia iieiia?iiio iini? aeaiaioa?iith ni?eith o
aiaeiiaiaeieo ?ic/eiieeao. I?ney aeaaeieoaaiiy eiioe. NH3 i?ioyaii ii/?
i?e 50 0N o?ioinoaoe ie?aiioeeaioeae?a aeae?eyee i?aia?aoeaiei
aeaeo?ioi?acii o iie?ae?eeai?aeiiio aae?.
Oaaeeoey 1
Iine?aeiaiino? neioaciaaieo ie?aiaeaciene?eaiioeeaioeae?a
NIine?aeiai?noue (5’-3’)Eiiieaiaioa?i?noue aei ae?eyiie 16S
??IE1d(CpsApsTpsApsGpsTpsTpsApsG) (9)eiiieaiaioa?iee
(499-507)2d(CpsTpsApsTpsGpsTpsApsTpsTpsA) (10)eiiieaiaioa?iee
(523-532)3d(GpsApsTpsTpsGpsApsTpsApsC) (9)ia?aeaeueiee
(499-507)4d(ApsTpsTpsApsTpsGpsTpsApsTpsC) (10)ia?aeaeueiee
(523-532)5d(CATAGTTAG) (9) eiiieaiaioa?iee (499-507)6d(CTATGTATTA)
(10)eiiieaiaioa?iee (523-532)I?ei?oea: ps – o?ioinoao
Anoaiiaeaii, ui iaoeai? ie?aiioeeaioeaee 5 ? 6 iiai?noth
a?ae?ie?cothoueny i?e eiioaeo? c ee?oeiaie i?eiieaci ca 6 aiae.
O?ioinoaoi? aiaeiae aeyaeeeny i?aeoe/ii iiai?noth no?eeeie aei ae??
ioeeaac i?ioyaii 3-o ae?a ?o aeniiceoe?? c ee?oeiaie iie?eoo?a.
Aeine?aeaeaiiy aieeao neioaoe/ieo ie?aiioeeaioeae?a ia o?aineyoe?th
iie?(U)-iao?eoe? a aacee?oeii?e nenoai? a?eeiaiai neioaco iieacaee
aoaeoeaia ?ia?aoaaiiy aeoeaiino? ?eainii (aei 21 %) i?e aeei?enoaii?
ie?aiioeeaioeaeo 1, oa o?ioe iaioa (aei 19 %) – ie?aiioeeaioeaeo 2 (?en.
7). Eiiieaiaioa?i? ie?aiia?e c ia?aeaeueiith iine?aeiai?noth (3 ? 4) ia
aieeaaee ia ??aaiue aeoeaiino? ?eainii aoieaieaci.
?ia?aoaaiiy, %
wmetafile8? ??!??????????? ???????yyy????????????
9ae???
????’yy???
????’yy??????????
????yyy????
???????uoy??????1/4???????”Arial??????-?????u??????1/4???I
“System?I???-????’yy???
????-?????yyy???? ???????9ae???????-????’yy???
????-?????yyy????
???????9ae???????AE?Ir?‘???-????’yy???
????-?????yyy???? ???????9ae????
???u?????????”????-?????)????????????)????
%????
-????U?%????U?-????«?%????«?-????z?%????z?-????J?%
????J?-?????%?????-????)????
E???)????)????o????o??????????????u
????u????@???@???…???…???E???E
???u??????????”????-????-????’yy???
????-?????-????yyy????
???????5a?????-????-????’yy???
????-?????-????yyy????
?????????%????-????-????’yy???
????-?????-????yyy???? ?????????%????ue??????
???-?
???u?????????”????-?????????o?)????????????ae?o???
?ae?o??????????????????T?u????T?u????7?@???7?@???
7?…
???u?????yyy?”????-?????????o?)????o?)????-????ue????
???????-????$?(?o?/?/?0?o?)?u????/?0????oe?4?
???$?3?oe?:?o?;?oe?4?/????o?;????o???
???$?>?o?E?o?F?o???oe????o?F????o?J?
???$?I?o?P?o?Q?o?J?o????o?Q????o?U?
???$?T?o?[?n?o?U?o????n??????`?
???$?_???f?i?g???`?n????i?g????i?k?
???$?j?i?n?i?o?i?k??????i?o????i?o????-????-????i?o???
?i?n????-????-????$?m?i?s?e?t?i?n?i????e?t????e?x?
???$?w?e??ae?~?ae?x?e????a?~????ae?‚????$?eiioeaio?aoe?y
ie?aiioeeaioeaeo, ieI
?en. 7
E?iaoe/i? aeine?aeaeaiiy neioaco a?eea a ee?oeiao iie?eoo?a iieacaee
iaae?iiy neioaco eeoa i?ney 4 aiae ?ieoaaoe?? c o?ioinoaoieie iio?aeieie
ie?aiioeeaioeae?a 1 ? 2 (ia 73 % a ee?oeiao M. fermentas PG-8 c
?aaaaioii 2) (Oaaeeoey 2). Ia iao iiaeyae, ie?aiioeeaioeaee ?ia?aothoue
a?eeiaee neioac ca ?aooiie eiiieaiaioa?ii? aca?iiae?? c a?aeiia?aeieie
“neaiaoo?ieie”, ooieoe?iiaeueii aaaeeeaeie aeey iie?eoo?a ae?eyieaie
neioaciaaii? “de novo” 16S ??IE, aeieoaaiiy i?noey ca’ycoaaiiy
?eainiiaeueiiai a?eea S4 oa iioeiaeaeaiiy a ?acoeueoao? oe??? aca?iiae??
cae?aiiy ?eainiiaeueii? 30S noaiaeeieoe?.
Oaaeeoey 2
I?eai?/aiiy neioaco a?eea a ee?oeiao iie?eoo?a o?ioinoaoieie aiaeiaaie
ie?aiaeaciene?eaiioeeaioeae?a (eiioeaio?aoe?y ?aaaaio?a 1 ieI)
Iie?eooe?aaaaioIia?aoaaiiy, %4 aiaeMycoplasma fermentas PG-18-0M.
fermentas PG-18164M. fermentas PG-18273Acholeplasma laidlawii
PG-8-0A.laidlawii PG-8157A.laidlawii PG-8261
I?i aoaeoeai?noue ?ia?aoaaiiy na?ae/eoue oa, ui i?e ?ieoaaoe??
A. laidlawii PG 8 c o?ioinoaoaie 1 oa 2 ?o ae?y ia i?ioeane o?aineyoe??
iii?oia aaea i?e eiioeaio?aoe?? aaaioa 0,5 ieI, a aeey ee?oei
M. fermentans – iaa?oue i?e 0,25 ieI (2 cieaeoaaa neioac a?ee?a iaeaea
ia 40 %). Iaeneiaeueiiai ?ia?aoaaiiy o?aineyoe?? aeinyaaee i?e 1 ieI.
Oaeei /eiii anoaiiaeaii, ui aioeneaiaoo?i?
ie?aiaeaciene?eaiioeeaioeaee, caoeuai? a?ae ae?? ioeeaac iiaeeo?eaoe??th
i?aeioeeaioeaeieo ca’yce?a, niaoeeo?/ii i?eai?/othoue o?aineyoe?th a
ee?oeiao iie?eoo?a ?ia?aoth/e ooieoe?iiaeueio aeoeai?noue ?o ?eainii.
Aeniea naeaeoeai?noue aioeneaiaoo?ieo ie?aiaeaciene?eaiioeeaioeae?a ?
ia?aaeoiiaith aeey oe?eani?yiiaaiiai noai?aiiy o?i?ioa?aiaaoe/ieo
cania?a i?ioe oeo /e ?ioeo caoaeiee?a oai?ia, /e ?o a?oi, ia oe?aeeeaeo
i?e oeueiio ?ioei i?e?ii?aai?ciai ? iae?ii?aai?cio.
AENIIAEE
1. ?ic?iaeai? iaoiaee neioaco aoeeee?/ieo ioeeaiceae?a – i??aceiiiiaeo ?
oei?iiaeo aiaeia?a aoeeeeia??o oa ?o aceaei- ? ae?eiceaeieo iio?aeieo:
N1- oa 2-I-(4-a?ae?ieneaooee)-, N1- oa 2-I-(4-aceaeiaooee)-,
N1-[4-(-D-?eaioo?aiiceeiene)-aooee]-3-aee?e-2-i??aceiii?a,
N1,N3-aee-(4-a?ae?ieneaooee)oei?io oa
N1,N3-aee-[4-(-D-?eaioo?aiiceeiene)-aooee]oei?io.
2. Neioaciaaii oa aeine?aeaeaii niaeo?aeuei? aeanoeaino? 30 iiaeo niieoe
(?*-, Ian-, 1I oa 13NssI?-niaeo?iiao??y). Ia?aa??ea iio?aeieo
i??aceiii?a ia ?o ?ia?aoth/o ae?th ia ?aie?eaoe?th ?yaeo a??onieo AeIE
oa ?IE in vitro ia iieacaea ?noioii? aeoeaiino?.
3. ?ic?iaeaii c?o/iee iaoiae neioaco ieiaiioeeaioeae?a, iiaeeoieiaaieo
?eaiioeeaiceaeii iiiaeaci[4,5-b]oaiaceio a 3’-iieiaeaii?. Iieacaii, ui
oeae ioeeaiceae ye aoaeoeaiee iioa?eaeyoi? a neeaaei iiaeeoieiaaieo
ieiaiioeeaioeae?a ?noioii iineeth? noaaieuei?noue eiiieaen?a c
eiiieaiaioa?ieie IE oa i?aeaeuo? no?ee?noue ie?aiia??a aei ae??
ee?oeiieo ioeeaac. Caaaeyee ?ioaineai?e oeoi?anoeaioe?? o?iiioi?a a?i
iiaea noaoe c?o/iith ?aii?oa?iith a?oiith aeey aeaoaeoe?? IE.
4. Noai?aii aoaeoeaiee ?aaaaio aeey i?yiiai oeoi?anoeaioiiai i?/aiiy
ioeeaiceae?a ? ie?aiioeeaioeae?a a i?ioean? ?o neioaco a oaa?aeioaciiio
aa??aio?, aai a ?ic/ei?. Iaea?aeai? oeoi?anoeaioii-i?/ai? ie?aiia?e
iiaeooue noaoe c?o/ieie aeey aeei?enoaiiy a iieaeoey?ii-a?ieia?/ieo
aeine?aeaeaiiyo ? a iaaeeoeei? ye aeueoa?iaoeaa ?cioiiiei i?oeai.
5. Neioaciaai? iiaeeo?eiaai? ii i?aeioeeaioeaeieo ca’yceao o?ioinoaoi?
aiaeiae ie?aiaeaciene?eaiioeeaioeae?a, eiiieaiaioa?i? aei a?aeiia?aeieo
neaiaoo?ieo ae?eyiie 16S ??IE iie?eoo?a. Anoaiiaeaii, ui aiie no?ee?
aei ae?? ioeeaac, aoaeoeaii e niaoeeo?/ii i?eai?/othoue o?aineyoe?th o
ee?oeiao iie?eoo?a oeyoii ?ia?aoaaiiy aeoeaiino? ?o ?eainii. Aeniea
naeaeoeai?noue aioeneaiaoo?ieo ie?aiaeaciene?eaiioeeaioeae?a ?
ia?aaeoiiaith aeey oe?eani?yiiaaiiai noai?aiiy ia ?o iniia?
aioei?e?iaieo o?i?ioa?aiaaoe/ieo cania?a, ia oe?aeeeaeo ?ioei
i?e?ii?aai?ciai ? iae?ii?aai?ciia?.
Nienie iioae?eiaaieo i?aoeue ca oaiith aeena?oaoe??
1. Davis J., Benhaddou R., Fedoryak O., Granet R., Krausz P., Bliard C.,
De Monte M., Aubertin A.M. Potential antiviral agents. Part II.
Synthesis and antiviral evaluation of pyrazinones substituted with
acyclic chains // Nucleosides & Nucleotides.-1998.-17, N 8.-P.
1489-1504.
2. Dubey I.Ya., Fedoryak O.D., Tkachuk O.M., Fedoryak D.M.. Preparation
of the fluorescein reagent for solid-phase oligonucleotide 5′-labelling
and its use for the synthesis of fluorescently labelled PCR primers for
HIV-1 detection // Aeiiieeia?u e eeaoea.- 1995.-11, ? 3-4.- N. 35-41.
3. Aai?ia I.A., Ne?eiaeue E.A., Aeoaae E.ss., Oaaei?ye I.Ae.,Oaaei?ye
Ae.I. Eiaeae?iaaiea o?aineyoeee in vivo o iieeeeooia oeioinoaoiuie
aiaeiaaie ieeaiaeaciene?eaiioeeaioeaeia. // I?e?ia?ie. ae. – 1996.-58,
? 4.- N. 11-19.
4. Cicoey. A.I., Aeaaie TH.I., Aeoaae I.ss., Oaaei?ye I.Ae., Ua?aaeiaa
A.N., Oaaei?ye Ae.I. Noaa?e?caoe?y aeoieaenieo oa o?eieaenieo eiiieaen?a
ie?aioei?aeeeaoo eiaaeaioii i?e?aeiaiei ae?eiceaeii ?i?aeacioaiaceio //
Aeiiieeia?u e eeaoea.-1998.-14, ? 1.-C. 54-61.
5. Aeoaae ?.ss., Oaaei?ye I.Ae., Oea/oe I.I., I?ieiiaiei A.A., Eoee
I.?., Oaaei?ye Ae.I. Oeoi?anoeaioiii?/ai? ie?aiioeeaioeaei? ciiaee aeey
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Oeoi?anoeaioiee ?aaaaio aeey oaa?aeioaciiai neioaco ia?aae?iaeoeaii
i?/aieo PCR i?aeia??a aeey aeaoaeoe?? HIV-1 // Ca??iee oac Ia?oi?
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7. Davis J.M., Fedoriak O., Benhaddou R., Granet R., Krausz P. Synthese
D’Analogues de L’Acyclovir de Type Pyrazinique // XVIemes Journees
Mediterraneennes des Glucides.-L’Isle-sur-la-Sorgue.-1996.
8. Davis J.M., Benhaddou R., Fedoriak O., Granet R., Krausz P. Synthese
de Nouveaux Analogues de L’Acyclovir // Journee “Chimie Organique:
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Fedoryak O.D. Modified components of nucleic acids: synthesis and
properties. – Manuscript.
Thesis for a candidate of sciences degree by speciality 02.00.10 –
bioorganic chemistry. – The Institute of Bioorganic Chemistry and
Petrochemistry of National Academy of Sciences of Ukraine, Kyiv, 1999.
The dissertation is devoted to the development of new effective methods
of the synthesis of modified oligodeoxyribonucleotides.
The synthesis of a series of 4’-substituted hydroxybutyl pyrazine and
hydroxybutyl thymine analogues of the anti-herpes compound, acyclovir,
is described. The transformations of the 4’ position of the hydroxybutyl
chain of hydroxyalkylated pyrazinones and thymine by azidation and by
glycosylation were studied. Some of the prepared compounds were tested
for their in vitro inhibitory effects on the replication of number of
DNA and RNA viruses. No antiviral activity was observed with compounds
substituted with an hydroxybutyl group. Modification of the 4’ position
of the hydroxyalkyl group by azidation or glicosylation did not improve
their activity.
A phenazine nucleoside derivative (Pzn) was covalently linked to the
3′-end of an oligothymidylate via a ribose residue of the dye glycoside.
Oligonucleotides were synthesized by H-phosphonate method on polymer
support with derivatised riboside of imidazo[4,5-b]phenazine. The effect
of such modification on duplex and triplex formation by (dT)10 with
(dA)15 and poly(dA)poly(dT) was studied. The attachment of Pzn strongly
enhanced the stability of these complexes due to the intercalation of
the dye chromophore into the dA and dAdT strands. Temperature of half
dissociation was increased by 12 oC for the duplex and by 20 oC for the
triplex formation.
A full synthetic protocol for the preparation of the fluorescein
H-phosphonate derivatives for oligonucleotide 5′-labelling during solid
phase synthesis was elaborated. Fluorescein H-phosphonate reagent was
used as a building block for solid phase oligonucleotide synthesis at
the last step.
Oligonucleotides were synthesized by H-phosphonate method using
Victoria 6M gene synthesizer with average coupling yields 98-98,5% per
step. After the chain elongation has completed the fluorescein reagent
was coupled to the 5′-hydroxyl group of oligonucleotide. The coupling
was carried out manually under standard conditions, as for nucleoside
H-phosphonates, except that coupling time was prolonged (4-5 min). The
coupling yields at this step were almost quantitative.
The use of the fluorescein reagent permits the efficient introduction of
the fluorescent label into oligonucleotides and nucleosides on solid
phase as well as in solution. This reagent can be used in solid phase
oligonucleotide synthesis without changing the ordinary synthesis,
deblocking and purification procedures, and significantly simplify the
preparation of fluorescein-labelled oligonucleotides.
Inhibition of mollicutes by synthetic oligonucleotides and their analogs
complementary to specific “signature” regions of 16S rRNA was studied.
Phosphorothioate oligonucleotide analogs were synthesized by standard
solid-phase H-phosphonate method followed by oxydation of H-phosphonate
oligomers with sulphur. It was shown that translation in vivo was
inhibited efficiently (up to 73%) by thiophosphate analogs of
oligonucleotides complementary to sequences 499-507 and 523-532 of 16S
rRNA.
Antisignature oligonucleotides are considered as superspecific agents
not leading to the development of resistance of mollicutes and believed
to be the main future remedy against diseases caused by microorganisms
lacking the system of nucleoside synthesis.
Key words: oligodeoxyribonucleotides, modification, fluorescent
labelling, imidazophenazine, thioanalogs, pyrazinones, antisignaturic
oligonucleotides.
Oaaei?ye I.Ae. Iiaeeo?eiaai? eiiiiiaioe ioeea?iiaeo eeneio: neioac ?
aeanoeaino?. – ?oeiien.
Aeena?oaoe?y ia caeiaoooy iaoeiaiai nooiaiy eaiaeeaeaoa o?i?/ieo iaoe ca
niaoe?aeuei?noth 02.00.10 – a?ii?aai?/ia o?i?y. – ?inoeooo a?ii?aai?/ii?
o?i?? oa iaooio?i?? IAI Oe?a?ie, Ee?a, 1999.
Aeena?oaoe?y i?enay/aia neioaco iiaeeo?eiaaieo
ie?aiaeaciene?eaiioeeaioeae?a (eii’thaaoe?y c ?aii?oa?ieie niieoeaie,
iiaeeo?eaoe?y i?aeioeeaioeaeieo ca’yce?a, aaoa?ioeeee?/ieo iniia,
aaaaeaiiy a ie?aiia? iai?e?iaeieo aiaeia?a ioeeaiceae?a) oa
aeine?aeaeaiith ?o aeanoeainoae.
?ic?iaeai? iaoiaee neioaco i??aceiiiiaeo ? oei?iiaeo aiaeia?a
aoeeeeia??o, ?o aceaei- oa ae?eiceeueiaaieo iio?aeieo. Iaea?aeaii
aoaeoeaiee I-oinoiiaoiee ?aaaaio aeey i?yiiai 5’-oeoi?anoeaioiiai
i?/aiiy ie?aiioeeaioeae?a a i?ioean? ?o neioaco. Noai?aiee c?o/iee
iaoiae iiaeeo?eaoe?? ie?aiioeeaioeae?a ioeeaiceaeiei iio?aeiei
?i?aeacioaiaceio, i?e?aeiaiei aei 3’-e?ioey ie?aiia?o. Iieacaii, ui
i?e?aeiaiee oaeei niiniaii iaeo?aeueiee oaiacei ?noioii i?aeaeuo?
noaa?euei?noue eiiieaen?a c IE. Neioaciaaii o?ioinoaoi? aiaeiae
ie?aiaeaciene?eaiioeeaioeae?a, eiiieaiaioa?i? aei neaiaoo?ieo ae?eyiie
16S ??IE iie?eoo?a, ye? aoaeoeaii ?ia?aothoue i?ioean o?aineyoe?? a
ee?oeiao oeeo i?e?ii?aai?ci?a.
Eeth/ia? neiaa: ie?aiaeaciene?eaiioeeaioeaee, iiaeeo?eaoe?y,
oeoi?anoeaioia i?/aiiy, ?i?aeacioaiacei, o?iaiaeiae, i??aceiiie,
aioeneaiaoo?i? ie?aiioeeaioeaee.
Oaaei?ye I.Ae. Iiaeeoeoee?iaaiiua eiiiiiaiou ioeeaeiiauo eeneio: neioac
e naienoaa. – ?oeiienue.
Aeenna?oaoeey ia nieneaiea o/aiie noaiaie eaiaeeaeaoa oeie/aneeo iaoe ii
niaoeeaeueiinoe 02.00.10 – aeii?aaie/aneay oeiey. – Einoeooo
aeii?aaie/aneie oeiee e iaooaoeiee IAI Oe?aeiu, Eeaa, 1999.
Aeenna?oaoeey iinayuaia neioaco iiaeeoeoee?iaaiiuo
ieeaiaeaciene?eaiioeeaioeaeia (eiiuethaaoeey n ?aii?oa?iuie
niaaeeiaieyie, iiaeeoeeaoeey iaaeioeeaioeaeiuo naycae,
aaoa?ioeeeee/aneeo iniiaaiee, aaaaeaiea a ieeaiia? iai?e?iaeiuo aiaeiaia
ioeeaiceaeia) e enneaaeiaaieth eo naienoa.
?ac?aaioaiu iaoiaeu neioaca ie?aceiiiiauo e oeieiiauo aiaeiaia
aoeeeeiae?a, eo aceaei- e aeeeiceee?iaaiiuo i?iecaiaeiuo. Iieo/ai
yooaeoeaiue I-oinoiiaoiue ?aaaaio aeey i?yiiai 5’-oeoi?anoeaioiiai
ia/aiey ieeaiioeeaioeaeia a i?ioeanna eo neioaca. Nicaeai oaeiaiue
iaoiae iiaeeoeeaoeee ieeaiioeeaioeaeia ioeeaiceaeiui i?iecaiaeiui
eieaeacioaiaceia, i?eniaaeeiaiiui e 3’-eiioeo ieeaiia?a. Iieacaii, /oi
i?eniaaeeiaiiue oaeei niiniaii iaeo?aeueiue oaiacei nouanoaaiii iiauoaao
noaaeeueiinoue eiiieaenia n IE. Neioace?iaaiu oeioinoaoiua aiaeiae
ieeaiaeaciene?eaiioeeaioeaeia, eiiieaiaioa?iua neaiaoo?iui o/anoeai 16S
??IE iieeeeooia, yooaeoeaii eiaeae?othuea i?ioeann o?aineyoeee a eeaoeao
yoeo iee?ii?aaieciia.
Eeth/aaua neiaa: ieeaiaeaciene?eaiioeeaioeaeu, iiaeeoeeaoeey,
oeoi?anoeaioiia ia/aiea, eieaeacioaiacei, oeiaiaeiae, ie?aceiiiu,
aioeneaiaoo?iua ieeaiioeeaioeaeu.
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