SYNTHETIC, STRUCTURAL, AND CONFORMATIONAL STUDIES OF METHYLATED RING-EXPANDED NUCLEOSIDES CONTAINING THE IMIDAZO[4,5-E][1,4]DIAZEPINE RING-SYSTEM

被引:17
作者
HOSMANE, RS [1 ]
BHAN, A [1 ]
HULCE, M [1 ]
ZHANG, HM [1 ]
HOSMANE, NS [1 ]
机构
[1] SO METHODIST UNIV,DEPT CHEM,DALLAS,TX 75275
来源
NUCLEOSIDES & NUCLEOTIDES | 1991年 / 10卷 / 04期
基金
美国国家科学基金会; 美国国家卫生研究院;
关键词
D O I
10.1080/07328319108046664
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
Syntheses of 4- and 7-methyl 4,5,7,8-tetrahydro-6H-3-(beta-D-ribofuranosyl)imidazo[4, 5-e] [1,4]diazepine-5,8-dione, 3 and 4, respectively, are reported. Single-crystal X-ray diffraction analysis of the aglycon of 3 aided in confirming the site of methylation in 3, and that of 4 in elucidating the solid state conformation of 4. Solution conformations of 3 and 4, along with their parent nucleoside 1 and the latter's 1-glycosyl regioisomer 2, were investigated by NOE and CD measurements.
引用
收藏
页码:819 / 836
页数:18
相关论文
共 17 条
[1]  
[Anonymous], 1974, INT TABLES XRAY CRYS, VIV
[2]  
Derome A. E., 1987, MODERN NMR TECHNIQUE
[3]  
HALL L D, 1980, Journal of the American Chemical Society, V102, P5703, DOI 10.1021/ja00538a001
[4]   PYRIMIDINE NUCLEOSIDE CONFORMATIONAL ANALYSIS - NUCLEAR OVERHAUSER EFFECT AND CIRCULAR DICHROISM CORRELATIONS [J].
HART, PA ;
DAVIS, JP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (03) :753-&
[5]  
HART PA, 1972, J AM CHEM SOC, V94, P511
[6]   THE SYNTHESIS AND BIOPHYSICAL INVESTIGATIONS OF NOVEL RING-EXPANDED NUCLEOSIDES, NUCLEOTIDES, AND HOMOPOLYMERS CONTAINING THE 5-7-FUSED HETEROCYCLIC RING-SYSTEM IMIDAZO[4,5-E][1,4]DIAZEPINE [J].
HOSMANE, RS ;
BHAN, A ;
KARPEL, RL ;
SIRIWARDANE, U ;
HOSMANE, NS .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (23) :5882-5890
[7]   THE SYNTHESIS OF 2 NOVEL RING EXPANDED XANTHINE NUCLEOSIDES CONTAINING THE IMIDAZO[4,5-E][1,4]DIAZEPINE RING-SYSTEM [J].
HOSMANE, RS ;
BHAN, A .
NUCLEOSIDES & NUCLEOTIDES, 1990, 9 (07) :913-922
[8]   CONFORMATIONAL STUDIES OF 2 ISOMERIC RING-EXPANDED PURINE NUCLEOSIDES AND THEIR 5'-MONOPHOSPHATE AND 5'-DIPHOSPHATE DERIVATIVES [J].
HOSMANE, RS ;
BHAN, A .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1989, 165 (01) :106-113
[9]  
HOSMANE RS, IN PRESS J HETEROCYC
[10]  
MARKIEWICZ WT, 1979, J CHEM RES-S, P24