Literature DB >> 31448618

Synthesis of 5-Dihydroxyboryluridine Phosphoramidite and Its Site-Specific Incorporation into Oligonucleotides for Probing Thymine DNA Glycosylase.

Sam Kavoosi1, Debasis Dey1, Kabirul Islam1.   

Abstract

A concise synthetic strategy to 5-dihydroxyboryldexoyuridine (5boU) phosphoramidite has been developed. 5boU was introduced into short oligonucleotides in a site-specific manner, demonstrating compatibility of the boronic acid moiety with standard solid-phase DNA synthesis chemistry. Electrophilic 5boU DNAs inhibited thymine DNA glycosylase, a cancer-relevant DNA-modifying enzyme. We envisage diverse applications of 5boU in organic synthesis, medicinal chemistry, and chemical biology.

Entities:  

Mesh：

Substances：

Year:  2019        PMID： 31448618      PMCID： PMC7042053          DOI： 10.1021/acs.orglett.9b02042

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  24 in total

1.  Borononucleotides as substrates/binders for human NMP kinases: enzymatic and spectroscopic evaluation.

Authors:  Chahrazade El Amri; Anthony R Martin; Jean-Jacques Vasseur; Michael Smietana
Journal:  Chembiochem       Date:  2012-06-25       Impact factor: 3.164

2.  Direct fluorescence monitoring of DNA base excision repair.

Authors:  Toshikazu Ono; Shenliang Wang; Chi-Kin Koo; Lisa Engstrom; Sheila S David; Eric T Kool
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-12       Impact factor: 15.336

3.  Specificity of human thymine DNA glycosylase depends on N-glycosidic bond stability.

Authors:  Matthew T Bennett; M T Rodgers; Alexander S Hebert; Lindsay E Ruslander; Leslie Eisele; Alexander C Drohat
Journal:  J Am Chem Soc       Date:  2006-09-27       Impact factor: 15.419

4.  Synthesis of DNA oligos containing 2'-deoxy-2'-fluoro-D-arabinofuranosyl-5-carboxylcytosine as hTDG inhibitor.

Authors:  Qing Dai; Xingyu Lu; Liang Zhang; Chuan He
Journal:  Tetrahedron       Date:  2012-04-14       Impact factor: 2.457

Review 5.  Molecular recognition with boronic acids-applications in chemical biology.

Authors:  Gillian F Whyte; Ramon Vilar; Rudiger Woscholski
Journal:  J Chem Biol       Date:  2013-06-01

6.  Discovery of boron-conjugated 4-anilinoquinazoline as a prolonged inhibitor of EGFR tyrosine kinase.

Authors:  Hyun Seung Ban; Taikou Usui; Wataru Nabeyama; Hidetoshi Morita; Kaori Fukuzawa; Hiroyuki Nakamura
Journal:  Org Biomol Chem       Date:  2009-08-20       Impact factor: 3.876

7.  AID/APOBEC deaminases disfavor modified cytosines implicated in DNA demethylation.

Authors:  Christopher S Nabel; Huijue Jia; Yu Ye; Li Shen; Hana L Goldschmidt; James T Stivers; Yi Zhang; Rahul M Kohli
Journal:  Nat Chem Biol       Date:  2012-07-08       Impact factor: 15.040

8.  Thymine DNA glycosylase specifically recognizes 5-carboxylcytosine-modified DNA.

Authors:  Liang Zhang; Xingyu Lu; Junyan Lu; Haihua Liang; Qing Dai; Guo-Liang Xu; Cheng Luo; Hualiang Jiang; Chuan He
Journal:  Nat Chem Biol       Date:  2012-02-12       Impact factor: 15.040

9.  Design and synthesis of boronic-acid-labeled thymidine triphosphate for incorporation into DNA.

Authors:  Na Lin; Jun Yan; Zhen Huang; Craig Altier; Minyong Li; Nicolas Carrasco; Mitsu Suyemoto; Lynette Johnston; Siming Wang; Qian Wang; Hao Fang; Julianne Caton-Williams; Binghe Wang
Journal:  Nucleic Acids Res       Date:  2007-01-31       Impact factor: 16.971

10.  Tet proteins can convert 5-methylcytosine to 5-formylcytosine and 5-carboxylcytosine.

Authors:  Shinsuke Ito; Li Shen; Qing Dai; Susan C Wu; Leonard B Collins; James A Swenberg; Chuan He; Yi Zhang
Journal:  Science       Date:  2011-07-21       Impact factor: 47.728
View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.