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 (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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