“Safety-catch”型保護基の特性を活用した硫酸化チロシン含有ペプチドの新規合成法の開発
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概要
- 論文の詳細を見る
Dimethylformamide-sulfur trioxide (DMF-SO<SUB>3</SUB>) complex was found to be more suitable for tyrosine sulfation than pyridine-sulfur trioxide (pyridine-SO<SUB>3</SUB>) 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<SUB>3</SUB> complex in the presence of nucleophile such as thiol or iodide ion. Based on these findings concerning DMF-SO<SUB>3</SUB> complex, a unique synthetic method for tyrosine-sulfate [Tyr(SO<SUB>3</SUB>H)] containing peptide was developed. In this methodology, the <I>p</I>-(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<SUB>3</SUB>H) residue was also developed. Several biologically active Tyr(SO<SUB>3</SUB>H) -containing peptides were prepared by this new method.
- 社団法人 有機合成化学協会の論文
著者
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北川 幸己
徳島大学薬学部
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二木 史朗
徳島大学薬学部
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二木 史朗
Faculty Of Pharmaceutical Sciences The University Of Tokushima
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二木 史朗
Faculty Of Pharmaceutical Sciences Kyoto University
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矢上 健
国立衛生試験所療品部
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