Efficient microwave-assisted tandem N- to S-acyl transfer and thioester exchange for the preparation of a glycosylated peptide thioester.
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.
Nagaike
Fumihiro
F
Department of Applied Biochemistry, Institute of Glycotechnology, Tokai University, Hiratsuka, Kanagawa, 259-1292, Japan.
Onuma
Yuko
Y
Kanazawa
Chie
C
Hojo
Hironobu
H
Ueki
Akiharu
A
Nakahara
Yuko
Y
Nakahara
Yoshiaki
Y
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
D004952:Esters; D010455:Peptides; D013438:Sulfhydryl Compounds; D015097:3-Mercaptopropionic Acid