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Titolo:
SYNTHESIS AND CHARACTERIZATION OF 8-METHOXY-2'-DEOXYADENOSINE-CONTAINING OLIGONUCLEOTIDES TO PROBE THE SYN GLYCOSIDIC CONFORMATION OF 2'-DEOXYADENOSINE WITHIN DNA
Autore:
EASON RG; BURKHARDT DM; PHILLIPS SJ; SMITH DP; DAVID SS;
Indirizzi:
UNIV CALIF SANTA CRUZ,DEPT CHEM & BIOCHEM SANTA CRUZ CA 95064 UNIV CALIF SANTA CRUZ,DEPT CHEM & BIOCHEM SANTA CRUZ CA 95064
Titolo Testata:
Nucleic acids research
fascicolo: 5, volume: 24, anno: 1996,
pagine: 890 - 897
SICI:
0305-1048(1996)24:5<890:SACO8>2.0.ZU;2-Z
Fonte:
ISI
Lingua:
ENG
Soggetto:
OXYTRICHA TELOMERIC DNA; DOUBLE HELICAL DNA; MOLECULAR-STRUCTURE; CRYSTAL-STRUCTURE; BACKBONE CONFORMATION; QUADRUPLEX STRUCTURE; BASE-PAIRS; MISMATCH; DUPLEX; MISPAIRS;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
37
Recensione:
Indirizzi per estratti:
Citazione:
R.G. Eason et al., "SYNTHESIS AND CHARACTERIZATION OF 8-METHOXY-2'-DEOXYADENOSINE-CONTAINING OLIGONUCLEOTIDES TO PROBE THE SYN GLYCOSIDIC CONFORMATION OF 2'-DEOXYADENOSINE WITHIN DNA", Nucleic acids research, 24(5), 1996, pp. 890-897

Abstract

The synthesis of 8-methoxy-2'-deoxyadenosine (moA) protected at N-6 as an N,N-dimethylformamidine derivative and incorporation of the modified nucleoside into oligodeoxynucleotides via the phosphoramidite method are described. UV thermal denaturation studies were conducted on duplexes containing moA:G, moA:C and moA:T base pairs to determine the thermodynamic stability of duplexes containing moA relative to their adenosine (A)-containing counterparts. In the case of moA:6 base pairs the effect of moA substitution is sequence dependent. In A:G mismatch-containing sequences, which have been shown by structural characterization to have a syn conformational preference at the glycosidic bond of A, moA substitution results in stabilization of the duplex. In contrast, in sequences where the A in the A:G mismatch has been shown to prefer the anti conformation moA substitution is destabilizing to the duplex. Thus moA may be a useful probe for investigating the conformational preferences of the N-glycosidic bond of adenosine within DNA. In addition, moA nucleoside is more resistant to acid-catalyzed depurinationthan previously described 8-bromo-2'-deoxyadenosine, allowing for facile incorporation into oligonucleotides via automated solid phase DNA synthesis.

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Documento generato il 21/09/20 alle ore 05:12:20