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

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.

SUBMITTER: Wu J

PROVIDER: S-EPMC8152807 | biostudies-literature | 2020 Mar

REPOSITORIES: biostudies-literature

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

Wu Jun J Kaplaneris Nikolaos N Ni Shaofei S Kaltenhäuser Felix F Ackermann Lutz L

Chemical science 20200324 25

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 strat ...[more]

PMID: 34094117

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