Efficient epimerization of pyrene and other aromatic C-nucleosides with trifluoroacetic acid in dichloromethane

被引：22

作者：

Jiang, YL ^{[1
]}

Stivers, JT ^{[1
]}

机构：

[1] Johns Hopkins Univ, Sch Med, Dept Pharmacol & Mol Sci, Baltimore, MD 21205 USA

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 01期

基金：

美国国家卫生研究院;

关键词：

epimerization; pyrene nucleoside; C-nucleosides; trifluoroacetic acid and dichloromethane;

D O I：

10.1016/S0040-4039(02)02481-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Trifluoroacetic acid has been found to be an efficient and non-oxidative catalyst for the epimerization of pyrene and other C-nucleosides in dichloromethane at ambient temperature. Aspects of the epimerization mechanism are also elucidated. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：85 / 88

页数：4

共 11 条

[1]

Chaudhuri NC, 1997, SYNLETT, P341

[2] ACID-CATALYZED ISOMERIZATION OF INDOL-3-YL SULFIDES TO INDOL-2-YL SULFIDES - UNEXPECTED INTERMOLECULAR NATURE OF THE REARRANGEMENT [J].

HAMEL, P ;

GIRARD, Y ;

ATKINSON, JG .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (01) :63-65

[3] ACID-CATALYZED ISOMERIZATION OF 3-INDOLYL SULFIDES TO 2-INDOLYL SULFIDES - 1ST SYNTHESIS OF 3-UNSUBSTITUTED 2-(ARYLTHIO)INDOLES - EVIDENCE FOR A COMPLEX INTERMOLECULAR PROCESS [J].

HAMEL, P ;

GIRARD, Y ;

ATKINSON, JG .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (09) :2694-2699

[4] Probing the limits of electrostatic catalysis by uracil DNA glycosylase using transition state mimicry and mutagenesis [J].

Jiang, YL ;

Drohat, AC ;

Ichikawa, Y ;

Stivers, JT .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2002, 277 (18) :15385-15392

[5] Base-flipping mutations of uracil DNA glycosylase: substrate rescue using a pyrene nucleotide wedge [J].

Jiang, YL ;

Stivers, JT ;

Song, FH .

BIOCHEMISTRY, 2002, 41 (37) :11248-11254

[6] Turning on uracil-DNA glycosylase using a pyrene nucleotide switch [J].

Jiang, YL ;

Kwon, K ;

Stivers, JT .

JOURNAL OF BIOLOGICAL CHEMISTRY, 2001, 276 (45) :42347-42354

[7] Acid-catalysed epimerization of indolo[2,3-a]quinolizidine derivatives:: Role of the nitrogen lone pairs in the mechanism [J].

Lounasmaa, M ;

Berner, M ;

Brunner, M ;

Suomalainen, H ;

Tolvanen, A .

TETRAHEDRON, 1998, 54 (34) :10205-10216

[8] A specific partner for abasic damage in DNA [J].

Matray, TJ ;

Kool, ET .

NATURE, 1999, 399 (6737) :704-708

[9] Efficient replication between non-hydrogen-bonded nucleoside shape analogs [J].

Morales, JC ;

Kool, ET .

NATURE STRUCTURAL BIOLOGY, 1998, 5 (11) :950-954

[10] Naphthalene, phenanthrene, and pyrene as DNA base analogues: Synthesis, structure, and fluorescence in DNA [J].

Ren, RXF ;

Chaudhuri, NC ;

Paris, PL ;

Rumney, S ;

Kool, ET .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (33) :7671-7678

← 1 2 →