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Phospha-Michael Addition as a New Click Reaction for Protein Functionalization.

ABSTRACT: A new type of click reaction between an alkyl phosphine and acrylamide was developed and applied for site-specific protein labeling in vitro and in live cells. Acrylamide is a small electrophilic olefin that readily undergoes phospha-Michael addition with an alkyl phosphine. Our kinetic study indicated a second-order rate constant of 0.07?m(-1) ?s(-1) for the reaction between tris(2-carboxyethyl)phosphine and acrylamide at pH?7.4. To demonstrate its application in protein functionalization, we used a dansyl-phosphine conjugate to successfully label proteins that were site-specifically installed with N(?) -acryloyl-l-lysine and employed a biotin-phosphine conjugate to selectively probe human proteins that were metabolically labeled with N-acryloyl-galactosamine.

SUBMITTER: Lee YJ

PROVIDER: S-EPMC5059841 | biostudies-literature | 2016 Mar

REPOSITORIES: biostudies-literature

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Phospha-Michael Addition as a New Click Reaction for Protein Functionalization.

Lee Yan-Jiun YJ Kurra Yadagiri Y Liu Wenshe R WR

Chembiochem : a European journal of chemical biology 20160216 6

A new type of click reaction between an alkyl phosphine and acrylamide was developed and applied for site-specific protein labeling in vitro and in live cells. Acrylamide is a small electrophilic olefin that readily undergoes phospha-Michael addition with an alkyl phosphine. Our kinetic study indicated a second-order rate constant of 0.07 m(-1) s(-1) for the reaction between tris(2-carboxyethyl)phosphine and acrylamide at pH 7.4. To demonstrate its application in protein functionalization, we u ...[more]

PMID: 26756316

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