Highly precise shape mimicry by a difluorotoluene deoxynucleoside, a replication-competent substitute for thymidine

被引：63
作者：
Guckian, KM [1 ]
Kool, ET [1 ]
机构：
[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 1997年 / 36卷 / 24期
关键词：
carbohydrates; conformation; hydrogen bonds; nucleosides; structure elucidation;
D O I：
10.1002/anie.199728251
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
[No abstract available]
引用
收藏
页码：2825 / 2828
页数：4
相关论文
共 22 条
[1]   CRYSTALLOGRAPHIC EVIDENCE FOR INTRAMOLECULAR C-H...O INTERACTIONS IN PRINCIPAL NUCLEOSIDES - REFINEMENT OF THE CRYSTAL-STRUCTURE OF THYMIDINE [J].
CHEKHLOV, AN .
JOURNAL OF STRUCTURAL CHEMISTRY, 1995, 36 (01) :155-161
[2]   SYNTHESIS AND PROPERTIES OF OLIGONUCLEOTIDES CONTAINING 2'-DEOXYNEBULARINE AND 2'-DEOXYXANTHOSINE [J].
ERITJA, R ;
HOROWITZ, DM ;
WALKER, PA ;
ZIEHLERMARTIN, JP ;
BOOSALIS, MS ;
GOODMAN, MF ;
ITAKURA, K ;
KAPLAN, BE .
NUCLEIC ACIDS RESEARCH, 1986, 14 (20) :8135-8153
[3]   SPECIFIC MUTAGENIC EFFECT OF BASE ANALOGUES ON PHAGE-T4 [J].
FREESE, E .
JOURNAL OF MOLECULAR BIOLOGY, 1959, 1 (02) :87-105
[4]   BIOCHEMICAL BASIS OF DNA-REPLICATION FIDELITY [J].
GOODMAN, MF ;
CREIGHTON, S ;
BLOOM, LB ;
PETRUSKA, J .
CRITICAL REVIEWS IN BIOCHEMISTRY AND MOLECULAR BIOLOGY, 1993, 28 (02) :83-126
[5]   How good is fluorine as a hydrogen bond acceptor? [J].
Howard, JAK ;
Hoy, VJ ;
OHagan, D ;
Smith, GT .
TETRAHEDRON, 1996, 52 (38) :12613-12622
[6]  
Kornberg A., 1992, DNA REPLICATION, P113
[7]  
LOEB LA, 1982, ANNU REV BIOCHEM, V52, P429
[8]   A thymidine triphosphate shape analog lacking Watson-Crick pairing ability is replicated with high sequence selectivity [J].
Moran, S ;
Ren, RXF ;
Kool, ET .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1997, 94 (20) :10506-10511
[9]   Difluorotoluene, a nonpolar isostere for thymine, codes specifically and efficiently for adenine in DNA replication [J].
Moran, S ;
Ren, RXF ;
Rumney, S ;
Kool, ET .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (08) :2056-2057
[10]   CONFORMATIONAL-ANALYSIS OF THE DEOXYRIBOFURANOSE RING IN DNA BY MEANS OF SUMS OF PROTON-PROTON COUPLING-CONSTANTS - A GRAPHICAL-METHOD [J].
RINKEL, LJ ;
ALTONA, C .
JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS, 1987, 4 (04) :621-649
123