Switch peptide via Staudinger reaction

Natalia Nepomniaschiy, Valerie Grimminger, Aviv Cohen, Saviana Digiovanni, Hilal A. Lashuel, Ashraf Brik

Research output: Contribution to journalArticle

32 Citations (Scopus)


(Chemical Equation Presented) A new transformation based on the Staudinger reaction is described, and its application in the design of a novel switch element to control peptide folding is demonstrated. We found that the azide switch is activated rapidly in water to promote acyl transfer using tris(2-carboxyethyl)phosphine hydrochloride (TCEP) via the Staudinger reaction. Our findings expand the repertoire of uses of the Staudinger reaction in chemical biology and the number of available triggers for use in switch peptides.

Original languageEnglish
Pages (from-to)5243-5246
Number of pages4
JournalOrganic Letters
Issue number22
Publication statusPublished - 1 Dec 2008


ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Nepomniaschiy, N., Grimminger, V., Cohen, A., Digiovanni, S., Lashuel, H. A., & Brik, A. (2008). Switch peptide via Staudinger reaction. Organic Letters, 10(22), 5243-5246. https://doi.org/10.1021/ol802268e