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Synthesis of Ureido-Linked Glycosylated Amino Acids from Nα-Fmoc-Asp/Glu-5-oxazolidinones and Their Application to Neoglycopeptide Synthesis

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Abstract:

A simple route for the synthesis of ureido-linked glycosylated amino acids has been described. The key step involves the reaction of isocyanates derived from Nα-Fmoc-Asp/Glu-5-oxazolidinones 1 with glycosyl amines followed by hydrolysis. The resulting ureido-linked glycosylated amino acids have been incorporated into peptides. The overall procedure is simple, high-yielding, and involves fewer steps.

Keywords: Curtius rearrangement; Nα-Fmoc-Asp/Glu-5-oxazolidinones; neoglycopeptides; ureido-linked glcosylated amino acids

Document Type: Research Article

DOI: http://dx.doi.org/10.1080/00397910802213711

Affiliations: Department of Studies in Chemistry, Central College Campus, Bangalore University, Bangalore, India

Publication date: January 1, 2008

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