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
StatePublished - Mar 18 2013
Externally publishedYes

Fingerprint

Condensation
DNA
Cyclization
Thymidine
2-cyanobenzothiazole
Molecules

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Rapid and specific post-synthesis modification of DNA through a biocompatible condensation of 1,2-aminothiols with 2-cyanobenzothiazole. / Cheng, Yunfeng; Peng, Hanjing; Chen, Weixuan; Ni, Nanting; Ke, Bowen; Dai, Chaofeng; Wang, Binghe.

In: Chemistry - A European Journal, Vol. 19, No. 12, 18.03.2013, p. 4036-4042.

Research output: Contribution to journalArticle

Cheng, Yunfeng ; Peng, Hanjing ; Chen, Weixuan ; Ni, Nanting ; Ke, Bowen ; Dai, Chaofeng ; Wang, Binghe. / Rapid and specific post-synthesis modification of DNA through a biocompatible condensation of 1,2-aminothiols with 2-cyanobenzothiazole. In: Chemistry - A European Journal. 2013 ; Vol. 19, No. 12. pp. 4036-4042.
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AU - Ke, Bowen

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