Hydrogen bonding between adenine and 2,4-difluorotoluene is definitely not present, as shown by concentration-dependent NMR studies

被引：22

作者：

Schmidt, KS

Sigel, RKO

Filippov, DV

van der Marel, GA

Lippert, B

Reedijk, J

机构：

[1] Leiden Univ, Leiden Inst Chem, Gorlaeus Labs, NL-2300 RA Leiden, Netherlands

[2] Univ Dortmund, Fachbereich Chem, D-44221 Dortmund, Germany

来源：

NEW JOURNAL OF CHEMISTRY | 2000年 / 24卷 / 04期

关键词：

D O I：

10.1039/a910295g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The chloroform-soluble nucleobase derivatives N-9-cyclohexylmethyladenine (A) and N-1-cyclohexylmethylthymine (T) have been synthesized in order to study hydrogen-bonding interactions between A and the thymidine mimic 2,4-difluorotoluene (F) in CDCl3 at high concentrations. Concentration-dependent H-1 NMR experiments show that in the presence of F, A undergoes self-association rather than pairing with F. These results strongly support the assumptions made by Kool with regard to the lack of hydrogen bonding between adenine and 2,4-difluorotoluene.(3).

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页码：195 / 197

页数：3

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共 20 条

[1] Interaction and solvation energies of nonpolar DNA base analogues and their role in polymerase insertion fidelity [J].

Barsky, D ;

Kool, ET ;

Colvin, ME .

JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS, 1999, 16 (06) :1119-1134

[2] STERIC EFFECTS IN DISPLACEMENT REACTIONS .7. THE BASE STRENGTHS AND ULTRAVIOLET ABSORPTION SPECTRA OF THE 2-MONOHALOPYRIDINES AND 3-MONOHALOPYRIDINES [J].

BROWN, HC ;

MCDANIEL, DH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (14) :3752-3755

[3] SYNTHETIC SPECTROSCOPIC MODELS RELATED TO COENZYMES AND BASE PAIRS .2. EVIDENCE FOR INTRAMOLECULAR BASE-BASE INTERACTIONS IN DINUCLEOTIDE ANALOGS [J].

BROWNE, DT ;

ESINGER, J ;

LEONARD, NJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (26) :7302-&

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

Evans, TA ;

Seddon, KR .

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

[5] Highly precise shape mimicry by a difluorotoluene deoxynucleoside, a replication-competent substitute for thymidine [J].

Guckian, KM ;

Kool, ET .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (24) :2825-2828

[6] Solution structure of a DNA duplex containing a replicable difluorotoluene-adenine pair [J].

Guckian, KM ;

Krugh, TR ;

Kool, ET .

NATURE STRUCTURAL BIOLOGY, 1998, 5 (11) :954-959

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

Howard, JAK ;

Hoy, VJ ;

OHagan, D ;

Smith, GT .

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

[8] DETECTION OF PROTON ACCEPTOR SITES OF HYDROGEN-BONDING BETWEEN NUCLEIC-ACID BASES BY USE OF C-13 MAGNETIC-RESONANCE [J].

IWAHASHI, H ;

KYOGOKU, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (24) :7761-7765

[9] AN INFRARED STUDY OF HYDROGEN BONDING BETWEEN ADENINE AND URACIL DERIVATIVES IN CHLOROFORM SOLUTION [J].

KYOGOKU, Y ;

LORD, RC ;

RICH, A .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (03) :496-+

[10] NMR STUDY OF HYDROGEN BONDING BETWEEN CHLOROFORM AND DIMETHYL SULFOXIDE, ETHYLENE, AND PROPYLENE [J].

MCCLELLAN, AL ;

NICKSIC, SW ;

GUFFY, JC .

JOURNAL OF MOLECULAR SPECTROSCOPY, 1963, 11 (05) :340-&