Angewandte Chemie. International edition in English 2009-01-01

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

Ahmed M Ali, Scott D Taylor

Index: Angew. Chem. Int. Ed. Engl. 48(11) , 2024-6, (2009)

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Abstract

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.