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

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Abstract

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.

Original languageEnglish
Pages (from-to)526-528
Number of pages3
JournalChemical and Pharmaceutical Bulletin
Volume37
Issue number2
DOIs
Publication statusPublished - 1989 Jan 1

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Keywords

  • Fmoc-based solid phase peptide synthesis
  • S-benzyloxymethylcysteine
  • S-protected cysteine sulfoxide
  • porcine brain natriuretic peptide synthesis
  • silver trifluoromethanesulfonate
  • thallium(lll) trifluoroacetate
  • trimethylsilyl bromide deprotection
  • trimethylsilyl trifluoromethanesulfonate deprotection

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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