Efficient solid-phase synthesis of sulfotyrosine peptides using a sulfate protecting-group strategy

Abstract

(Chemical Equation Presented) 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. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.