Efficient solid-phase synthesis of sulfotyrosine peptides using a sulfate protecting-group strategy.
Double protection: Efficient Fmoc-based solid-phase synthesis (SPPS) of sulfotyrosine (sY) peptides is achieved by incorporating the sY residue(s) as a dichlorovinyl-protected (DCV) sulfodiester(s) and using 2-methylpiperidine for Fmoc removal. After removal of the other protecting groups, the DCV group could be cleaved by mild hydrogenolysis giving the sY peptides in good yield.
Ali
Ahmed M
AM
Department of Chemistry, University of Waterloo, 200 University Ave. West, Waterloo, Ontario, N2L 3G1, Canada.
Taylor
Scott D
SD
D000595:Amino Acid Sequence; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D010880:Piperidines / Q000737:chemistry; D013440:Sulfides / Q000737:chemistry*; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D010455:Peptides; D010880:Piperidines; D013440:Sulfides; C046482:2-methylpiperidine; C005662:tyrosine O-sulfate; D014443:Tyrosine