Solid phase synthesis of glycopeptides using Shoda's activation of unprotected carbohydrates

An expedient and simple protocol to access S-linked glycopeptides by Fmoc SPPS using unprotected carbohydrates is reported. The utility of the method was demonstrated with the solid phase synthesis of a MUC1 fragment (20 mer) containing two glycosylation sites that were substituted with S-linked gly...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2013-01, Vol.49 (69), p.7608-7610
Main Authors: Novoa, Alexandre, Barluenga, Sofia, Serba, Christelle, Winssinger, Nicolas
Format: Article
Language:English
Subjects:
Activation
Amino Acid Sequence
Carbohydrates
Carbohydrates - chemistry
Fragmentation
Glycan
Glycopeptides
Glycopeptides - chemical synthesis
Glycopeptides - chemistry
Glycosylation
Molecular Sequence Data
Mucin-1 - chemistry
Solid phase synthesis
Solid-Phase Synthesis Techniques
Utilities
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Summary:An expedient and simple protocol to access S-linked glycopeptides by Fmoc SPPS using unprotected carbohydrates is reported. The utility of the method was demonstrated with the solid phase synthesis of a MUC1 fragment (20 mer) containing two glycosylation sites that were substituted with S-linked glycans.
ISSN:1359-7345
1364-548X
DOI:10.1039/c3cc43458c