Dimethylformamide-sulfur trioxide (DMF-SO
3) complex was found to be more suitable for tyrosine sulfation than pyridine-sulfur trioxide (pyridine-SO
3) complex, the most commonly used sulfur trioxide complex for sulfation. In addition, a new method for the effective reduction of methionine sulfoxide [Met(O)] in protected peptides was established using DMF-SO
3 complex in the presence of nucleophile such as thiol or iodide ion. Based on these findings concerning DMF-SO
3 complex, a unique synthetic method for tyrosine-sulfate [Tyr(SO
3H)] containing peptide was developed. In this methodology, the
p-(methylsulfinyl) benzyl : (Msib) group, a safety-catch type protecting group, was used as a key protecting group for the alcoholic hydroxyl function of Ser/Thr in order to achieve the selective sulfation on Tyr. An effective acidic deprotection system to minimize the decomposition of sulfate ester on Tyr(SO
3H) residue was also developed. Several biologically active Tyr(SO
3H) -containing peptides were prepared by this new method.
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