title: Straightforward entry to S-glycosylated fmoc-amino acids and their application to solid phase synthesis of glycopeptides and glycopeptidomimetics.
abstract: 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.
authors.affiliation: Institute of Biostructures and Bioimaging, National Research Council , Napoli, Italy.
authors.forename: Daniela
authors.initials: D
authors.lastname: Comegna
authors.forename: Ivan
authors.initials: I
authors.lastname: de Paola
authors.forename: Michele
authors.initials: M
authors.lastname: Saviano
authors.forename: Annarita
authors.initials: A
authors.lastname: Del Gatto
authors.forename: Laura
authors.initials: L
authors.lastname: Zaccaro
mesh_terms: D000595:Amino Acid Sequence; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D005449:Fluorenes / Q000138:chemical synthesis* / Q000737:chemistry; D006020:Glycopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D015394:Molecular Structure; D060327:Solid-Phase Synthesis Techniques; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D002241:Carbohydrates; D005449:Fluorenes; D006020:Glycopeptides; C016456:N(alpha)-fluorenylmethyloxycarbonylamino acids