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
收藏
页码：4969 / 4972
页数：4
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