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. 2024 Mar 1;89(5):3390-3402.
doi: 10.1021/acs.joc.3c02823. Epub 2024 Feb 20.

Pd(II)-Catalyzed β-C(sp3)-H Alkynylation of Alanine in Di- and Tripeptides with Asn as an Endogenous Directing Group

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Pd(II)-Catalyzed β-C(sp3)-H Alkynylation of Alanine in Di- and Tripeptides with Asn as an Endogenous Directing Group

Xing-Xing Ding et al. J Org Chem. .

Abstract

The introduction of alkyne moieties into peptides remains in demand as it represents a promising approach for further structural diversification of peptides. Herein, we describe the Pd(II)-catalyzed C(sp3)-H alkynylation of Ala-Asn-embedded di- and tripeptides using Asn as the endogenous lead group. In addition, a key building block for the glycopeptide Tyc4PG-14 and Tyc4PG-15 was produced by our methodology.

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