Nickel(II)-promoted amide N-H arylation of pyroglutamate-histidine with arylboronic acid reagents

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

doi:10.1021/acs.orglett.9b00759

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 journal › Article › peer-review

15 Citations (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 language	English
Pages (from-to)	2445-2448
Number of pages	4
Journal	Organic Letters
Volume	21
Issue number	7
DOIs	https://doi.org/10.1021/acs.orglett.9b00759
Publication status	Published - 2019 Apr 5
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.9b00759

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title = "Nickel(II)-promoted amide N-H arylation of pyroglutamate-histidine with arylboronic acid reagents",

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.",

author = "Kengo Hanaya and Miller, {Mary K.} and Ball, {Zachary T.}",

note = "Funding Information: We acknowledge support from the Robert A. Welch Foundation Research Grant C-1680 (Z.T.B.), from the National Science Foundation under grant number CHE-1055569 (Z.T.B.). We thank David Yang (Rice University) for experimental assistance. Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

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doi = "10.1021/acs.orglett.9b00759",

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T1 - Nickel(II)-promoted amide N-H arylation of pyroglutamate-histidine with arylboronic acid reagents

AU - Hanaya, Kengo

AU - Miller, Mary K.

AU - Ball, Zachary T.

N1 - Funding Information: We acknowledge support from the Robert A. Welch Foundation Research Grant C-1680 (Z.T.B.), from the National Science Foundation under grant number CHE-1055569 (Z.T.B.). We thank David Yang (Rice University) for experimental assistance. Publisher Copyright: © 2019 American Chemical Society.

PY - 2019/4/5

Y1 - 2019/4/5

N2 - 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.

AB - 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.

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Nickel(II)-promoted amide N-H arylation of pyroglutamate-histidine with arylboronic acid reagents

Abstract

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