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Efficient Solid‐Phase Synthesis of Sulfotyrosine Peptides using a Sulfate Protecting‐Group Strategy
Author(s) -
Ali Ahmed M.,
Taylor Scott D.
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200805642
Subject(s) - hydrogenolysis , protecting group , chemistry , solid phase synthesis , residue (chemistry) , peptide synthesis , combinatorial chemistry , yield (engineering) , group (periodic table) , peptide , stereochemistry , phase (matter) , organic chemistry , catalysis , biochemistry , materials science , alkyl , metallurgy
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.