Streamlined access to S-glycosylated Fmoc-amino acids was developed. The process provides diverse glycosylated modified amino acids in high yield and stereoselectivity taking advantage of the in situ generation of a glycosylthiolate obtained from carbohydrate acetates in a few steps. Mild basic conditions make the conjugation reaction compatible with Fmoc-iodo-amino acids. To validate the strategy the glycosylated building blocks were used for SPPS and the unprecedented incorporation of a long thio-oligosaccharide to the peptide chain was demonstrated.

This study developed a streamlined process for producing S-glycosylated Fmoc-amino acids in high yield and stereoselectivity, enabling the synthesis of glycopeptides and glycopeptidomimetics in solid phase.

Paper

Straightforward entry to S-glycosylated fmoc-amino acids and their application to solid phase synthesis of glycopeptides and glycopeptidomimetics.

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