Straightforward Entry to S-Glycosylated Fmoc-Amino Acids and Their Application to Solid Phase Synthesis of Glycopeptides and Glycopeptidomimetics

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• 作者：Daniela Comegna ; Ivan de Paola ; Michele Saviano ; Annarita Del Gatto ; Laura Zaccaro
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：February 6, 2015
• 年：2015
• 卷：17
• 期：3
• 页码：640-643
• 全文大小：319K
• ISSN：1523-7052

文摘

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.