S-BENZYLOXYMETHYLCYSTEINE, ITS PROPERTIES AND APPLICATION IN THE SYNTHESIS OF PORCINE BRAIN NATRIURETIC PEPTIDE (pBNP)1, 2)

Akira Otaka, Hiroshi Morimoto, Nobutaka Fuji, Takaki Koide, Susumu Funakoshi, Haruaki Yajima

研究成果: Article査読

7 被引用数 (Scopus)

抄録

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 (AgOTf)/TFA or 1 M trimethylsilyl trifluoromethanesulfonate (TMSOTf)-thioanisole/TFA. Cys(Bom) can be converted to cystine by treatment with thallium(lll) triffuoroacetate. 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-fluorenylmethytoxycarbonyl]. In the final step, the peptide-resin was first treated with AgOTf/TFA, then with 1 M trimethylsilyl bromide-thioanisole/TFA. After dithiothreitol treatment and subsequent air-oxidation, a homogeneous pBNP was obtained in 17% yield, based on the first amino acid loaded on the resin. The result was compared with those produced by other alternative deprotecting procedures.

本文言語English
ページ(範囲)526-528
ページ数3
ジャーナルChemical and Pharmaceutical Bulletin
37
2
DOI
出版ステータスPublished - 1989
外部発表はい

ASJC Scopus subject areas

  • 化学 (全般)
  • 創薬

フィンガープリント

「S-BENZYLOXYMETHYLCYSTEINE, ITS PROPERTIES AND APPLICATION IN THE SYNTHESIS OF PORCINE BRAIN NATRIURETIC PEPTIDE (pBNP)<sup>1,</sup> <sup>2)</sup>」の研究トピックを掘り下げます。これらがまとまってユニークなフィンガープリントを構成します。

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