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

[41] SYN ANTI-CONFORMATIONAL ANALYSIS OF REGULAR AND MODIFIED NUCLEOSIDES BY 1D H-1 NOE DIFFERENCE SPECTROSCOPY - A SIMPLE GRAPHICAL-METHOD BASED ON CONFORMATIONALLY RIGID MOLECULES [J].

ROSEMEYER, H ;

TOTH, G ;

GOLANKIEWICZ, B ;

KAZIMIERCZUK, Z ;

BOURGEOIS, W ;

KRETSCHMER, U ;

MUTH, HP ;

SEELA, F .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (22) :5784-5790

[42]

SAENGER W, 1984, PRINCIPLES NUCLEIC A, P69

[43] PURINE NUCLEOSIDE PHOSPHORYLASE - ISOLATION AND CHARACTERIZATION [J].

SEDIVA, K ;

VOTRUBA, I ;

HOLY, A ;

ROSENBERG, I .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1990, 55 (12) :2987-2999

[44] SYNTHESIS AND PROPERTIES OF CONFORMATIONALLY LOCKED 1,3-BISALKYL-7-DEAZAXANTHINE 2'-DEOXY-D-RIBOFURANOSIDES [J].

SEELA, F ;

KRETSCHMER, U .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1990, 27 (03) :479-486

[45]

SHELDRICK GM, 1990, SHELXTL PLUS

[46] DETERMINATION OF THE ANOMERIC CONFIGURATION OF 2'-DEOXY-D-RIBONUCLEOSIDES BY H-1-NMR AND BY CRYSTALLOGRAPHIC STUDIES OF A NOVEL 2'-DEOXY C-NUCLEOSIDE [J].

SRIVASTAVA, PC ;

ROBBINS, RK ;

TAKUSAGAWA, F ;

BERMAN, HM .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1981, 18 (08) :1659-1662

[47]

UMEZAWA H, Patent No. 58159494

[48]

UMEZAWA H, 1975, Patent No. 2453649

[49]

WOO PWK, 1974, J HETEROCYCLIC CHEM, V11, P641, DOI 10.1002/jhet.5570110438

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