title: Efficient microwave-assisted tandem N- to S-acyl transfer and thioester exchange for the preparation of a glycosylated peptide thioester.
abstract: A peptide carrying a mercaptomethylated proline derivative at the C-terminus was prepared by solid-phase peptide synthesis (SPPS) and converted to the thioester of 3-mercaptopropionic acid (MPA) by aqueous MPA under microwave irradiation conditions. This post-SPPS thioesterification reaction was successfully applied to the synthesis of a glycopeptide thioester composed of 25 amino acid (AA) residues, which was then used for the preparation of a 61-AA glycopeptide by the thioester condensation method.
authors.affiliation: Department of Applied Biochemistry, Institute of Glycotechnology, Tokai University, Hiratsuka, Kanagawa, 259-1292, Japan.
authors.forename: Fumihiro
authors.initials: F
authors.lastname: Nagaike
authors.forename: Yuko
authors.initials: Y
authors.lastname: Onuma
authors.forename: Chie
authors.initials: C
authors.lastname: Kanazawa
authors.forename: Hironobu
authors.initials: H
authors.lastname: Hojo
authors.forename: Akiharu
authors.initials: A
authors.lastname: Ueki
authors.forename: Yuko
authors.initials: Y
authors.lastname: Nakahara
authors.forename: Yoshiaki
authors.initials: Y
authors.lastname: Nakahara
mesh_terms: D015097:3-Mercaptopropionic Acid / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D004952:Esters / Q000737:chemistry*; D006031:Glycosylation; D008872:Microwaves; D010084:Oxidation-Reduction; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D013438:Sulfhydryl Compounds
chemical_list: D004952:Esters; D010455:Peptides; D013438:Sulfhydryl Compounds; D015097:3-Mercaptopropionic Acid