Profiling base excision repair glycosylases with synthesized transition state analogs

被引：22

作者：

Chu, Aurea M. ^{[1
]}

Fettinger, James C. ^{[1
]}

David, Sheila S. ^{[1
]}

机构：

[1] Univ Calif Davis, Dept Chem, Davis, CA 95616 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2011年 / 21卷 / 17期

基金：

美国国家卫生研究院;

关键词：

Base excision repair; DNA glycosylase; Pyrrolidine analogs; Transition state analogs; 8-Oxo-7,8-dihydro-2-deoxyguanosine; hOGG1; Fpg; Nei; hNEIL1; HUMAN DNA GLYCOSYLASE; RICIN A-CHAIN; SUBSTRATE-SPECIFICITY; RECOGNITION; REMOVAL; ENZYME; OXIDATION; KINETICS; BINDING; DAMAGE;

D O I：

10.1016/j.bmcl.2011.05.085

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Two base excision repair glycosylase (BER) transition state (TS) mimics, (3R,4R)-1-benzyl (hydroxymethyl) pyrrolidin-3-ol (1NBn) and (3R,4R)-(hydroxymethyl) pyrrolidin-3-ol (1N), were synthesized using an improved method. Several BER glycosylases that repair oxidized DNA bases, bacterial formamidopyrimdine glycosylase (Fpg), human OG glycosylase (hOGG1) and human Nei-like glycosylase 1 (hNEIL1) exhibit exceptionally high affinity (K-d similar to pM) with DNA duplexes containing the 1NBn and 1N nucleotide. Notably, comparison of the K-d values of both TS mimics relative to an abasic analog (THF) in duplex contexts paired opposite C or A suggest that these DNA repair enzymes use distinctly different mechanisms for damaged base recognition and catalysis despite having overlapping substrate specificities. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：4969 / 4972

页数：4

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