title: An Fmoc compatible, O to S shift-mediated procedure for the preparation of C-terminal thioester peptides.
abstract: We report a practical 2-hydroxy-3-mercapto-propionic acid (Hmp)/2-methylpiperidine (2-MP) based Fmoc chemistry procedure to prepare the C-terminal Hmp peptides, which serve as the precursors of C-terminal thioester peptides. The subsequent O to S acyl shift and thiol-exchange mediated thioester conversion of the crude precursor peptides can be accomplished smoothly under mild conditions to provide the desired thioester peptides with good yield and high quality. This is a highly adaptable approach, and we envision its broad application in the preparation of C-terminal thioester peptides.
authors.affiliation: Lilly Research Laboratories, Indianapolis, Indiana 46285, United States.
authors.forename: Fa
authors.initials: F
authors.lastname: Liu
authors.forename: John P
authors.initials: JP
authors.lastname: Mayer
mesh_terms: D000596:Amino Acids / Q000737:chemistry*; D005449:Fluorenes / Q000737:chemistry*; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D010880:Piperidines / Q000737:chemistry*; D020539:Sequence Analysis, Protein; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C496789:9-fluorenylmethoxycarbonyl; D000596:Amino Acids; D005449:Fluorenes; D010455:Peptides; D010880:Piperidines; D013438:Sulfhydryl Compounds; C046482:2-methylpiperidine; C008361:beta-mercaptolactate