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Literature DB >> 21689934

Profiling base excision repair glycosylases with synthesized transition state analogs.

Aurea M Chu¹, James C Fettinger, Sheila S David.

Abstract

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)∼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.

Entities: CellLine Chemical Disease Gene Mutation Species

Mesh：

Substances：

Year: 2011 PMID： 21689934 PMCID： PMC3156346 DOI： 10.1016/j.bmcl.2011.05.085

Source DB: PubMed Journal: Bioorg Med Chem Lett ISSN： 0960-894X Impact factor: 2.823

40 in total

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2. Structural characterization of human 8-oxoguanine DNA glycosylase variants bearing active site mutations.

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Review 3. Mechanisms of formation, genotoxicity, and mutation of guanine oxidation products.

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Review 4. Base-excision repair of oxidative DNA damage.

Authors: Sheila S David; Valerie L O'Shea; Sucharita Kundu
Journal: Nature Date: 2007-06-21 Impact factor: 49.962

Review 5. Toward a detailed understanding of base excision repair enzymes: transition state and mechanistic analyses of N-glycoside hydrolysis and N-glycoside transfer.

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Journal: Chem Rev Date: 2006-02 Impact factor: 60.622

Review 6. Chemical glycobiology.

Authors: C R Bertozzi; L L Kiessling
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8. Transition state analogues rescue ribosomes from saporin-L1 ribosome inactivating protein.

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9. A practical synthesis of (3R,4R)-N-tert-butoxycarbonyl-4-hydroxymethylpyrrolidin-3-ol.

Authors: Keith Clinch; Gary B Evans; Richard H Furneaux; Dirk H Lenz; Jennifer M Mason; Simon P H Mee; Peter C Tyler; Sarah J Wilcox
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11 in total

1. Targeting Base Excision Repair Glycosylases with DNA Containing Transition State Mimics Prepared via Click Chemistry.

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2. Selective base excision repair of DNA damage by the non-base-flipping DNA glycosylase AlkC.

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3. Surprising repair activities of nonpolar analogs of 8-oxoG expose features of recognition and catalysis by base excision repair glycosylases.

Authors: Paige L McKibbin; Akio Kobori; Yosuke Taniguchi; Eric T Kool; Sheila S David
Journal: J Am Chem Soc Date: 2012-01-09 Impact factor: 15.419

Profiling base excision repair glycosylases with synthesized transition state analogs.

1. Ultrasensitive in situ visualization of active glucocerebrosidase molecules.

2. Structural characterization of human 8-oxoguanine DNA glycosylase variants bearing active site mutations.

Review 3. Mechanisms of formation, genotoxicity, and mutation of guanine oxidation products.

Review 4. Base-excision repair of oxidative DNA damage.

Review 5. Toward a detailed understanding of base excision repair enzymes: transition state and mechanistic analyses of N-glycoside hydrolysis and N-glycoside transfer.

Review 6. Chemical glycobiology.

7. Ricin A-chain substrate specificity in RNA, DNA, and hybrid stem-loop structures.

8. Transition state analogues rescue ribosomes from saporin-L1 ribosome inactivating protein.

9. A practical synthesis of (3R,4R)-N-tert-butoxycarbonyl-4-hydroxymethylpyrrolidin-3-ol.

10. A divergent asymmetric approach to aza-spiropyran derivative and (1S,8aR)-1-hydroxyindolizidine.

1. Targeting Base Excision Repair Glycosylases with DNA Containing Transition State Mimics Prepared via Click Chemistry.

2. Selective base excision repair of DNA damage by the non-base-flipping DNA glycosylase AlkC.

3. Surprising repair activities of nonpolar analogs of 8-oxoG expose features of recognition and catalysis by base excision repair glycosylases.

4. Repair of hydantoin lesions and their amine adducts in DNA by base and nucleotide excision repair.

5. The DNA glycosylase AlkD uses a non-base-flipping mechanism to excise bulky lesions.

6. Structural Basis for Finding OG Lesions and Avoiding Undamaged G by the DNA Glycosylase MutY.

7. Fe-S Clusters and MutY Base Excision Repair Glycosylases: Purification, Kinetics, and DNA Affinity Measurements.

8. Structural Insights into the Mechanism of Base Excision by MBD4.

9. Ethyl 4-hy-droxy-1-methyl-5-oxo-2-phenyl-pyrrolidine-3-carboxyl-ate 1.25-hydrate.

10. A chemical and kinetic perspective on base excision repair of DNA.