The enzymatic synthesis and ant HIV-1 activity of 9-beta-D-2 ',3 '-dideoxynucleosides of N(6)-substituted purines

被引:6
作者
Betbeder, D. [1 ]
Hutchinson, D. W. [1 ]
Richards, A. O'L [1 ]
Mahood, N. [2 ]
Kinchington, D. [3 ]
机构
[1] Warwick Univ, Chem Dept, Coventry CV4 7AL, W Midlands, England
[2] Med Res Council Collaborat Ctr, London NW7 1AD, England
[3] St Marys Hosp, Med Sch, Dept Med Microbiol, Div Virol, London WC2 1PG, England
关键词
D O I
10.1177/095632029000100404
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
9-beta-D-2',3'-dideoxyribonucleosides of four N(6)-substituted purines and 1-deazapurine were prepared using crude nucleoside N-deoxyribosyltransferases (EC 2.4.2.6) from Lactobacillus leichmannii. The 2',3'-dideoxynucleosides derived from N(6)-substituted purines (1-4) are inhibitors of the replication of human immunodeficiency virus type 1 (HIV-1), with EC90 values in the range 20-100 and 20-200 mu m, depending on the cell line used, and have low in vitro toxicity at their effective concentrations.
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收藏
页码:249 / 253
页数:5
相关论文
共 17 条
[1]  
Balzarini J., 1988, CLIN USE ANTIVIRAL D, P361
[2]   REACTIONS OF RELEVANCE TO CHEMISTRY OF AMINOGLYCOSIDE ANTIBIOTICS .7. CONVERSION OF THIOCARBONATES INTO DEOXY-SUGARS [J].
BARTON, DHR ;
SUBRAMANIAN, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1977, (15) :1718-1723
[3]   THE STEREOSELECTIVE ENZYMATIC-SYNTHESIS OF 9-BETA-D-2'-DEOXYRIBOFURANOSYL 1-DEAZAPURINE [J].
BETBEDER, D ;
HUTCHINSON, DW ;
RICHARDS, AO .
NUCLEIC ACIDS RESEARCH, 1989, 17 (11) :4217-4222
[4]   THE ENZYMATIC-SYNTHESIS OF IMIDAZOLE DEOXYNUCLEOSIDES - 1-BETA-D-2'-DEOXYRIBOFURANOSYL-5-AMINOIMIDAZOLE-4-CARBOXAMIDE AND 1-BETA-D-2'-DEOXYRIBOFURANOSYLBENZIMIDAZOLE [J].
BETBEDER, D ;
HUTCHINSON, DW .
NUCLEOSIDES & NUCLEOTIDES, 1990, 9 (04) :569-577
[5]   SYNTHESIS OF 2',3'-DIDEOXYNUCLEOSIDES BY ENZYMATIC TRANS-GLYCOSYLATION [J].
CARSON, DA ;
WASSON, DB .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1988, 155 (02) :829-834
[6]   COMPARATIVE ACTIVITY OF 2',3'-SATURATED AND UNSATURATED PYRIMIDINE AND PURINE NUCLEOSIDES AGAINST HUMAN IMMUNODEFICIENCY VIRUS TYPE-1 IN PERIPHERAL-BLOOD MONONUCLEAR-CELLS [J].
CHU, CK ;
SCHINAZI, RF ;
ARNOLD, BH ;
CANNON, DL ;
DOBOSZEWSKI, B ;
BHADTI, VB ;
GU, ZP .
BIOCHEMICAL PHARMACOLOGY, 1988, 37 (19) :3543-3548
[7]   BROAD-SPECTRUM ANTIRETROVIRAL ACTIVITY OF 2',3'-DIDEOXYNUCLEOSIDES [J].
DAHLBERG, JE ;
MITSUYA, H ;
BLAM, SB ;
BRODER, S ;
AARONSON, SA .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1987, 84 (08) :2469-2473
[8]  
Koszalka G. W., 1986, PROCESS PREPARATION, Patent No. 0206497 A2
[9]  
Koszalka G. W., 1988, THERAPEUTIC NUCLEOSI, Patent No. 0286425 A2
[10]  
LIN TS, 1987, BIOCHEM PHARMACOL, V36, P2713