Switch peptide via Staudinger reaction

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

doi:10.1021/ol802268e

Switch peptide via Staudinger reaction

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

39 Scopus citations

Abstract

(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 language	English
Pages (from-to)	5243-5246
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	22
DOIs	https://doi.org/10.1021/ol802268e
State	Published - 1 Dec 2008

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol802268e

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title = "Switch peptide via Staudinger reaction",

abstract = "(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.",

author = "Natalia Nepomniaschiy and Valerie Grimminger and Aviv Cohen and Saviana Digiovanni and Lashuel, \{Hilal A.\} and Ashraf Brik",

year = "2008",

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doi = "10.1021/ol802268e",

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journal = "Organic Letters",

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T1 - Switch peptide via Staudinger reaction

AU - Nepomniaschiy, Natalia

AU - Grimminger, Valerie

AU - Cohen, Aviv

AU - Digiovanni, Saviana

AU - Lashuel, Hilal A.

AU - Brik, Ashraf

PY - 2008/12/1

Y1 - 2008/12/1

N2 - (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.

AB - (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.

UR - https://www.scopus.com/pages/publications/58149203498

U2 - 10.1021/ol802268e

DO - 10.1021/ol802268e

M3 - Article

AN - SCOPUS:58149203498

SN - 1523-7060

VL - 10

SP - 5243

EP - 5246

JO - Organic Letters

JF - Organic Letters

IS - 22

ER -

Switch peptide via Staudinger reaction

Abstract

ASJC Scopus subject areas

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