A Vinylogous Photocleavage Strategy Allows Direct Photocaging of Backbone Amide Structure

Alicia E. Mangubat-Medina, Samuel C. Martin, Kengo Hanaya, Zachary T. Ball

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Side-chain modifications that respond to external stimuli provide a convenient approach to control macromolecular structure and function. Responsive modification of backbone amide structure represents a direct and powerful alternative to impact folding and function. Here, we describe a new photocaging method using histidine-directed backbone modification to selectively modify peptides and proteins at the amide N-H bond. A new vinylogous photocleavage method allows photorelease of the backbone modification and, with it, restoration of function.

Original languageEnglish
Pages (from-to)8401-8404
Number of pages4
JournalJournal of the American Chemical Society
Volume140
Issue number27
DOIs
Publication statusPublished - 2018 Jul 11
Externally publishedYes

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Amides
Histidine
Peptides
Restoration
Proteins

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

A Vinylogous Photocleavage Strategy Allows Direct Photocaging of Backbone Amide Structure. / Mangubat-Medina, Alicia E.; Martin, Samuel C.; Hanaya, Kengo; Ball, Zachary T.

In: Journal of the American Chemical Society, Vol. 140, No. 27, 11.07.2018, p. 8401-8404.

Research output: Contribution to journalArticle

Mangubat-Medina, Alicia E. ; Martin, Samuel C. ; Hanaya, Kengo ; Ball, Zachary T. / A Vinylogous Photocleavage Strategy Allows Direct Photocaging of Backbone Amide Structure. In: Journal of the American Chemical Society. 2018 ; Vol. 140, No. 27. pp. 8401-8404.
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