Difluorotoluene, a thymine isostere, does not hydrogen bond after all

被引：38

作者：

Wang, X ^{[1
]}

Houk, KN ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Biochem & Chem, Los Angeles, CA 90095 USA

来源：

CHEMICAL COMMUNICATIONS | 1998年 / 23期

关键词：

D O I：

10.1039/a807425i

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The lack of significant hydrogen bonding by 2,4-difluorotoluene, an isostere of thymine, is confirmed by ab initio calculations and force field modelling of nucleic acids.

引用

页码：2631 / 2632

页数：2

共 23 条

[1]

ECHOLS H, 1991, ANNU REV BIOCHEM, V60, P477, DOI 10.1146/annurev.biochem.60.1.477

[2] Hydrogen bonding in DNA - a return to the status quo [J].

Evans, TA ;

Seddon, KR .

CHEMICAL COMMUNICATIONS, 1997, (21) :2023-2024

[3] Experimental measurement of aromatic stacking affinities in the context of duplex DNA [J].

Guckian, KM ;

Schweitzer, BA ;

Ren, RXF ;

Sheils, CJ ;

Paris, PL ;

Tahmassebi, DC ;

Kool, ET .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (34) :8182-8183

[4] How good is fluorine as a hydrogen bond acceptor? [J].

Howard, JAK ;

Hoy, VJ ;

OHagan, D ;

Smith, GT .

TETRAHEDRON, 1996, 52 (38) :12613-12622

[5]

Jeffrey G.A., 1997, An Introduction to Hydrogen Bonding, VVolume 12

[6] Bi-stranded, multisite replication of a base pair between difluorotoluene and adenine: confirmation by 'inverse' sequencing [J].

Liu, DY ;

Moran, S ;

Kool, ET .

CHEMISTRY & BIOLOGY, 1997, 4 (12) :919-926

[7] FIDELITY OF DNA-SYNTHESIS [J].

LOEB, LA ;

KUNKEL, TA .

ANNUAL REVIEW OF BIOCHEMISTRY, 1982, 51 :429-457

[8] Quantum-chemical ab initio study on the adenine-difluorotoluene complex -: A mimic for the adenine-thymine base pair [J].

Meyer, R ;

Sühnel, J .

JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS, 1997, 15 (03) :619-624

[9] MACROMODEL - AN INTEGRATED SOFTWARE SYSTEM FOR MODELING ORGANIC AND BIOORGANIC MOLECULES USING MOLECULAR MECHANICS [J].

MOHAMADI, F ;

RICHARDS, NGJ ;

GUIDA, WC ;

LISKAMP, R ;

LIPTON, M ;

CAUFIELD, C ;

CHANG, G ;

HENDRICKSON, T ;

STILL, WC .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1990, 11 (04) :440-467

[10] 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

← 1 2 3 →