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)

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 languageEnglish
Pages (from-to)5243-5246
Number of pages4
JournalOrganic Letters
Volume10
Issue number22
DOIs
Publication statusPublished - 1 Dec 2008
Externally publishedYes

Fingerprint

peptides
switches
Switches
Peptides
Azides
hydrochlorides
biology
phosphines
folding
Water
actuators
water
tris(2-carboxyethyl)phosphine

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry

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

Switch peptide via Staudinger reaction. / Nepomniaschiy, Natalia; Grimminger, Valerie; Cohen, Aviv; Digiovanni, Saviana; Lashuel, Hilal A.; Brik, Ashraf.

In: Organic Letters, Vol. 10, No. 22, 01.12.2008, p. 5243-5246.

Research output: Contribution to journalArticle

Nepomniaschiy, N, Grimminger, V, Cohen, A, Digiovanni, S, Lashuel, HA & Brik, A 2008, 'Switch peptide via Staudinger reaction', Organic Letters, vol. 10, no. 22, pp. 5243-5246. https://doi.org/10.1021/ol802268e
Nepomniaschiy N, Grimminger V, Cohen A, Digiovanni S, Lashuel HA, Brik A. Switch peptide via Staudinger reaction. Organic Letters. 2008 Dec 1;10(22):5243-5246. https://doi.org/10.1021/ol802268e
Nepomniaschiy, Natalia ; Grimminger, Valerie ; Cohen, Aviv ; Digiovanni, Saviana ; Lashuel, Hilal A. ; Brik, Ashraf. / Switch peptide via Staudinger reaction. In: Organic Letters. 2008 ; Vol. 10, No. 22. pp. 5243-5246.
@article{01e1fa67c0b74a99aff47d4b07bb6ad4,
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",
month = "12",
day = "1",
doi = "10.1021/ol802268e",
language = "English",
volume = "10",
pages = "5243--5246",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "22",

}

TY - JOUR

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 - http://www.scopus.com/inward/record.url?scp=58149203498&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=58149203498&partnerID=8YFLogxK

U2 - 10.1021/ol802268e

DO - 10.1021/ol802268e

M3 - Article

VL - 10

SP - 5243

EP - 5246

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 22

ER -