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

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 N ^α-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
• N ^α-Fmoc-Asp/Glu-5-oxazolidinones
• neoglycopeptides
• ureido-linked glcosylated amino acids

ACKNOWLEDGMENTS

Authors are grateful to the Department of Science and Technology, Government of India, for financial support. R. V. is grateful to the CSIR for the award of a fellowship.

Notes

^a HRMS.

^b ES-MS.