A NEW SYNTHESIS OF SOME 4'-THIO-(D)UNDER-BAR-RIBONUCLEOSIDES AND PRELIMINARY ENZYMATIC EVALUATION

被引：31

作者：

LEYDIER, C ^{[1
]}

BELLON, L ^{[1
]}

BARASCUT, JL ^{[1
]}

DEYDIER, J ^{[1
]}

MAURY, G ^{[1
]}

PELICANO, H ^{[1
]}

ELALAOUI, MA ^{[1
]}

IMBACH, JL ^{[1
]}

机构：

[1] UNIV MONTPELLIER 2,CHIM BIOORGAN LAB,CNRS,URA 488,F-34095 MONTPELLIER 5,FRANCE

来源：

NUCLEOSIDES & NUCLEOTIDES | 1994年 / 13卷 / 10期

关键词：

D O I：

10.1080/15257779408013205

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A new synthesis of 4'-thioribonucleosides is presented together with the enzymatic evaluation of the adenosine analogues with respect to adenosine kinase. The 4-thio-D-ribofuranosyl carbohydrate precursor ($) under bar 7 was obtained in good yield from D-ribose and further reacted with adenine and cytosine to give the a and beta anomers of 4'-thioadenosine and 4'-thiocytidine, respectively. 4'-thio-beta-($) under bar D-adenosine, ($) under bar 12 beta, is a poor substrate for bovine liver adenosine kinase but does not show substrate inhibition of the enzyme.

引用

页码：2035 / 2050

页数：16

共 37 条

[1] PRODRUGS OF 9-BETA-D-ARABINOFURANOSYLADENINE .1. SYNTHESIS AND EVALUATION OF SOME 5'-(O-ACYL) DERIVATIVES [J].

BAKER, DC ;

HASKELL, TH ;

PUTT, SR .

JOURNAL OF MEDICINAL CHEMISTRY, 1978, 21 (12) :1218-1221

[2] 2,3,5-TRI-O-BENZYL-D-RIBOSYL AND -L-ARABINOSYL BROMIDES [J].

BARKER, R ;

FLETCHER, HG .

JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (11) :4605-&

[3] EFFECT OF ACYCLIC PYRIMIDINES RELATED TO 9-[(1,3-DIHYDROXY-2-PROPOXY)METHYL]GUANINE ON HERPESVIRUSES [J].

BEAUCHAMP, LM ;

SERLING, BL ;

KELSEY, JE ;

BIRON, KK ;

COLLINS, P ;

SELWAY, J ;

LIN, JC ;

SCHAEFFER, HJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (01) :144-149

[4] EFFICIENT SYNTHESIS OF 4-THIO-D-RIBOFURANOSE AND SOME 4'-THIORIBONUCLEOSIDES [J].

BELLON, L ;

BARASCUT, JL ;

IMBACH, JL .

NUCLEOSIDES & NUCLEOTIDES, 1992, 11 (08) :1467-1479

[5] SUGAR MODIFIED OLIGONUCLEOTIDES - SYNTHESIS, NUCLEASE RESISTANCE AND BASE-PAIRING OF OLIGODEOXYNUCLEOTIDES CONTAINING 1-(4'-THIO-BETA-D-RIBOFURANOSYL)-THYMINE [J].

BELLON, L ;

MORVAN, F ;

BARASCUT, JL ;

IMBACH, JL .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1992, 184 (02) :797-803

[6]

BELLON L, 1992, NUCLEIC ACIDS RES, V21, P1587

[7]

BENNETT LL, 1975, MOL PHARMACOL, V11, P803

[8] ROLE OF 5'-HYDROXYL GROUP OF ADENOSINE IN DETERMINING SUBSTRATE SPECIFICITY FOR ADENOSINE DEAMINASE [J].

BLOCH, A ;

ROBINS, MJ ;

MCCARTHY, JR .

JOURNAL OF MEDICINAL CHEMISTRY, 1967, 10 (05) :908-&

[9] PREPARATION AND ACTIVITY OF 4'-THIO DERIVATIVES OF SOME 6-SUBSTITUTED PURINE NUCLEOSIDES [J].

BOBEK, M ;

WHISTLER, RL ;

BLOCK, A .

JOURNAL OF MEDICINAL CHEMISTRY, 1970, 13 (03) :411-&

[10]

DYSON MR, 1991, CARBOHYD RES, V216, P237

← 1 2 3 4 →