Nickel(II)-Promoted Amide N-H Arylation of Pyroglutamate-Histidine with Arylboronic Acid Reagents

Kengo Hanaya, Mary K. Miller, Zachary T. Ball

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Small and simple bioorthogonal reactive handles that can be readily encoded by natural processes are important for bioconjugation. A rapid nickel-promoted N-H arylation of pyroglutamate-histidine sequences with 2-nitroarylboronic acids proceeds under mild aqueous conditions. Chemoselective activation of a lactam amide N-H within a peptide or protein provides a new approach to selective conjugation in polyamide structures.

Original languageEnglish
JournalOrganic Letters
DOIs
Publication statusPublished - 2019 Jan 1
Externally publishedYes

Fingerprint

Pyrrolidonecarboxylic Acid
Lactams
histidine
Nylons
Nickel
conjugation
Histidine
Amides
amides
peptides
reagents
Chemical activation
nickel
activation
proteins
Peptides
acids
Acids
Proteins

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Nickel(II)-Promoted Amide N-H Arylation of Pyroglutamate-Histidine with Arylboronic Acid Reagents. / Hanaya, Kengo; Miller, Mary K.; Ball, Zachary T.

In: Organic Letters, 01.01.2019.

Research output: Contribution to journalArticle

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