Rapid and specific post-synthesis modification of DNA through a biocompatible condensation of 1,2-aminothiols with 2-cyanobenzothiazole

Yunfeng Cheng, Hanjing Peng, Weixuan Chen, Nanting Ni, Bowen Ke, Chaofeng Dai, Binghe Wang

Research output: Contribution to journalArticle

Abstract

Post-synthesis modification of DNA is an important way of functionalizing DNA molecules. Herein, we describe a method that first enzymatically incorporates a cyanobenzothiazole (CBT)-modified thymidine. The side-chain handle CBT can undergo a rapid and site-specific cyclization reaction with 1,2-aminothiols to afford DNA functionalization in aqueous solution. Another key advantage of this method is the formation of a single stereo/regioisomer in the process, which allows for precise control of DNA modification to yield a single component for aptamer selection work and other applications. The first enzymatic incorporation of a cyanobenzothiazole (CBT)-modified thymidine has been developed. The side-chain handle CBT can undergo a rapid and site-specific cyclization reaction with 1,2-aminothiols to enable DNA functionalization in aqueous solution. A key advantage of this method is the formation of a single stereo/regioisomer in the process, which allows for precise control of DNA modification to yield a single component (see scheme).

Original languageEnglish (US)
Pages (from-to)4036-4042
Number of pages7
JournalChemistry - A European Journal
Volume19
Issue number12
DOIs
Publication statusPublished - Mar 18 2013
Externally publishedYes

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Keywords

  • bioorthogonal reactions
  • click chemistry
  • cyanobenzothiazole
  • DNA
  • post-synthesis modification

ASJC Scopus subject areas

  • Chemistry(all)

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