Late-stage C(sp2)–H and C(sp3)–H glycosylation of C-aryl/alkyl glycopeptides: mechanistic insights and fluorescence labeling

Jun Wu; Nikolaos Kaplaneris; Shaofei Ni; Felix Kaltenhäuser; Lutz Ackermann

doi:10.1039/D0SC01260B

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Late-stage C(sp²)–H and C(sp³)–H glycosylation of C-aryl/alkyl glycopeptides: mechanistic insights and fluorescence labeling†‡

Jun Wu,§^a Nikolaos Kaplaneris,§^a Shaofei Ni,^a Felix Kaltenhäuser^a and Lutz Ackermann

*^ab

Author affiliations

* Corresponding authors

^a Institut fuer Organische und Biomolekulare Chemie, Georg-August-Universitaet Gottingen, Tammannstrasse 2, 37077 Goettingen, Germany
E-mail: Lutz.Ackermann@chemie.uni-goettingen.de

^b German Center for Cardiovascular Research (DZHK), Potsdamer Strasse 58, 10785 Berlin, Germany

Abstract

C(sp³)–H and C(sp²)–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 C-alkyl glycoamino acids, glycopeptides and C-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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Article information

DOI: https://doi.org/10.1039/D0SC01260B
Article type: Edge Article
Submitted: 01 Mar 2020
Accepted: 23 Mar 2020
First published: 24 Mar 2020
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2020,11, 6521-6526

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Late-stage C(sp²)–H and C(sp³)–H glycosylation of C-aryl/alkyl glycopeptides: mechanistic insights and fluorescence labeling

J. Wu, N. Kaplaneris, S. Ni, F. Kaltenhäuser and L. Ackermann, Chem. Sci., 2020, 11, 6521 DOI: 10.1039/D0SC01260B

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