THE SYNTHESIS, STRUCTURE, AND CONFORMATION OF 2'-DEOXY ANALOGS OF FAT XANTHINE NUCLEOSIDES, CONTAINING THE IMIDAZO[4,5-E][1,4]DIAZEPINE RING-SYSTEM

被引：15

作者：

BHAN, A ^{[1
]}

HOSMANE, RS ^{[1
]}

机构：

[1] UNIV MARYLAND,DEPT CHEM & BIOCHEM,CHEM DYNAM LAB,CATONSVILLE,MD 21228

来源：

NUCLEOSIDES & NUCLEOTIDES | 1992年 / 11卷 / 06期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1080/07328319208018334

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：

The syntheses of 1-(2-deoxy-beta-D-erythro-pentofuranosyl)-4,5,7,8-tetrahydro-6H-imidazo[4,5-e][1,4]diazepine-5,8-dione (9-beta), its 3-glycosyl regioisomer (16-beta), and their respective alpha anomers (9-alpha and 16-alpha), are reported. Conformational and configurational studies, employing H-1 NMR NOE and CD spectroscopy, are described. The single-crystal X-ray structural analysis of 9-beta is presented. The attempted enzymic glycosylation of the heterocyclic base 6 with a bacterial purine nucleoside phosphorylase was not successful.

引用

页码：1175 / 1200

页数：26

共 49 条

[1] STRUCTURE OF A REARRANGEMENT PRODUCT - 1-METHYL-3-(5-AMINO-1-BENZYLIMIDAZOL-4-YL)-1,2,4-TRIAZOLE, C13H14N6 [J].

AFSHAR, C ;

BERMAN, HM ;

SAWZIK, P ;

LESSINGER, L ;

LIM, BB ;

HOSMANE, RS .

JOURNAL OF CRYSTALLOGRAPHIC AND SPECTROSCOPIC RESEARCH, 1987, 17 (04) :533-543

[2]

Agarwal RP, 1978, CHEM BIOL NUCLEOSIDE, P159

[3]

[Anonymous], 1974, INT TABLES XRAY CRYS, VIV

[4] STUDIES RELATED TO THE TOTAL SYNTHESIS OF PENTOSTATIN - APPROACHES TO THE SYNTHESIS OF (8R)-3,6,7,8-TETRAHYDROIMIDAZO-[4,5-D][1,3]DIAZEPIN-8-OL AND N-3 ALKYL CONGENERS [J].

BAKER, DC ;

PUTT, SR ;

SHOWALTER, HDH .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (03) :629-634

[5] TOTAL SYNTHESIS OF PENTOSTATIN, THE POTENT INHIBITOR OF ADENOSINE-DEAMINASE [J].

BAKER, DC ;

PUTT, SR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (20) :6127-6128

[6] THE REACTION OF 5-AMINOIMIDAZOLE-4-CARBOHYDRAZIDES WITH ORTHO-ESTERS [J].

BRIDSON, PK ;

DAVIS, RA ;

RENNER, LS .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1985, 22 (03) :753-755

[7] TOTAL SYNTHESIS OF (8R)-3-(2-DEOXY-BETA-D-ERYTHRO-PENTOFURANOSYL)-3,6,7,8-TETRAHYDROIMIDAZO[4,5-D][1,3]DIAZEPIN-8-OL (PENTOSTATIN), THE POTENT INHIBITOR OF ADENOSINE-DEAMINASE [J].

CHAN, E ;

PUTT, SR ;

SHOWALTER, HDH ;

BAKER, DC .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (18) :3457-3464

[8] ALTERNATIVE SYNTHESES OF AZEPINOMYCIN [J].

FUJII, T ;

SAITO, T ;

FUJISAWA, T .

HETEROCYCLES, 1988, 27 (05) :1163-1166

[9]

GLAZER RI, 1980, REV DRUG METAB DRUG, V3, P105

[10] EVIDENCE FOR THE CONVERSION OF ADENOSINE TO 2'-DEOXYCOFORMYCIN BY STREPTOMYCES-ANTIBIOTICUS [J].

HANVEY, JC ;

HARDMAN, JK ;

SUHADOLNIK, RJ ;

BAKER, DC .

BIOCHEMISTRY, 1984, 23 (05) :904-907

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