Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 5, Pages 1597-1602Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja110115a
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Funding
- National Institutes of Health [CA103823]
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Described herein is a method for the joining of complex peptides to complex oligosaccharides via an N-linkage. The omega-aspartylation is conducted by coupling fully deprotected glycosylamine with a peptide containing a unique thioacid at the omega-aspartate carboxyl. In the presence of HOBT, under conditions that, in principle, allow for oxidation, complex components are combined in encouraging yields to produce structurally and stereochemically defined N-linked glycopolypeptides wherein the carbohydrate domain can be quite complex. Various mechanisms for oxidative coupling are proposed.
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