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 language | English |
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Pages (from-to) | 526-528 |
Number of pages | 3 |
Journal | Chemical and Pharmaceutical Bulletin |
Volume | 37 |
Issue number | 2 |
DOIs | |
Publication status | Published - 1989 |
Externally published | Yes |
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