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Peptidyl ?-Asp Selenoesters Enable Efficient Synthesis of N-Linked Glycopeptides.

ABSTRACT: Chemical synthesis is an attractive approach allows for the assembly of homogeneous complex N-linked glycopeptides and glycoproteins, but the limited coupling efficiency between glycans and peptides hampered the synthesis and research in the related field. Herein we developed an alternative glycosylation to construct N-linked glycopeptide via efficient selenoester-assisted aminolysis, which employs the peptidyl ?-asparagine selenoester and unprotected glycosylamine to perform rapid amide-bond ligation. This glycosylation strategy is highly compatible with the free carboxylic acids and hydroxyl groups of peptides and carbohydrates, and readily available for the assembly of structure-defined homogeneous N-linked glycopeptides, such as segments derived from glycoprotein EPO and IL-5.

SUBMITTER: Du JJ

PROVIDER: S-EPMC7232547 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Peptidyl ω-Asp Selenoesters Enable Efficient Synthesis of N-Linked Glycopeptides.

Du Jing-Jing JJ Zhang Lian L Gao Xiao-Fei XF Sun Hui H Guo Jun J

Frontiers in chemistry 20200505

Chemical synthesis is an attractive approach allows for the assembly of homogeneous complex N-linked glycopeptides and glycoproteins, but the limited coupling efficiency between glycans and peptides hampered the synthesis and research in the related field. Herein we developed an alternative glycosylation to construct N-linked glycopeptide via efficient selenoester-assisted aminolysis, which employs the peptidyl ω-asparagine selenoester and unprotected glycosylamine to perform rapid ...[more]

PMID: 32478036

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