S-BENZYLOXYMETHYLCYSTEINE, ITS PROPERTIES AND APPLICATION IN THE SYNTHESIS OF PORCINE BRAIN NATRIURETIC PEPTIDE (pBNP)
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概要
- 論文の詳細を見る
The properties of S-benzyloxymethylcysteine, Cys(Bom), were examined. The S-Bom group is stable to trifluoroacetic acid (TFA), but is easily cleaved by treatment with silver trifluoromethanesulfonate (AgOTl)/TFA or 1 M trimethylsilyl trifluoromethanesulfonate (TMSOTf)-thioanisole/TFA. Cys(Bom) can be converted to cystine by treatment with thallium(III) trifluoroacetate.Cys(Bom)was successfully applied to the Fmoc-based solid phase synthesis of porcine brain natriuretic peptide (pBNP), a 26-residue peptide with one disulfide bond [Fmoc=9-fluorenylmethyloxycarbonyl]. In the final step, the peptide-resin was first treated with AgOTl/TFA, then with 1 M trimethyisllyl bromide-thioanisole/TFA. After dithiothreitol treatment and subsequent air-oxidation, a homogeneous pBNP was obtained in 17% yiled, based on the first amino acid loaded on the resin. The results was compared with those produced by other alternative deprotecting procedures.
- 公益社団法人日本薬学会の論文
- 1989-02-25
著者
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藤井 信孝
京都大学薬学部
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大高 章
Faculty of Pharmaceutical Sciences, Kyoto University
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藤井 信孝
Faculty of Pharmaceutical Sciences, Kyoto University
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小出 隆規
Faculty of Pharmaceutical Sciences, Kyoto University
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矢島 治明
Faculty of Pharmaceutical Sciences, Kyoto University
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船越 奨
Faculty of Pharmaceutical Sciences
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大高 章
徳島大学大学院ヘルスバイオサイエンス研究部
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大高 章
京都大学 薬
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大高 章
京大 大学院薬学研究科
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矢島 治明
京都大学
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船越 奨
Faculty Of Pharmaceutical Sciences Kyoto University
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矢島 治明
京大・薬
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藤井 信孝
京大 薬
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矢島 治明
Faculty Of Pharmaceutical Sciences Kyoto University
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森本 啓氏
Faculty of Pharmaceutical Sciences
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小出 隆規
Faculty Of Pharmaceutical Sciences Kyoto University
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藤井 信孝
京都大学
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森本 啓氏
Faculty Of Pharmaceutical Sciences Kyoto University
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