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

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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.

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詳細情報 詳細情報について

  • CRID
    1573105977298811136
  • NII論文ID
    110003627547
  • NII書誌ID
    AA00602100
  • ISSN
    00092363
  • 本文言語コード
    en
  • データソース種別
    • CiNii Articles

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