Late-stage C(sp)-H and C(sp)-H Glycosylation of -aryl/alkyl Glycopeptides: Mechanistic Insights and Fluorescence Labeling

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2021 Jun 7

PMID 34094117

Citations 18

Authors

Jun Wu

Nikolaos Kaplaneris

Shaofei Ni

Felix Kaltenhauser

Lutz Ackermann

Affiliations

Soon will be listed here.

Abstract

C(sp)-H and C(sp)-H glycosylations of structurally complex amino acids and peptides were accomplished through the assistance of triazole peptide-isosteres. The palladium-catalyzed peptide-saccharide conjugation provided modular access to structurally complex -alkyl glycoamino acids, glycopeptides and -aryl glycosides, while enabling the assembly of fluorescent-labeled glycoamino acids. The C-H activation approach represents an expedient and efficient strategy for peptide late-stage diversification in a programmable as well as chemo-, regio-, and diastereo-selective fashion.

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