Studies on Peptides. LXXXIII. Behavior of S-Substituted Cysteine Sulfoxides under Deprotecting Conditions in Peptide Synthesis

S FUNAKOSHI, N FUJII, K AKAJI, H IRIE…

Index: Funakoshi; Fujii; Akaji; et al. Chemical and Pharmaceutical Bulletin, 1979 , vol. 27, # 9 p. 2151 - 2156

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Citation Number: 14

Abstract

Sulfoxides of Cys (Sp-methoxybenzyl) and Cys (S-benzyl) were prepared by oxidation with sodium perborate. Hydrogen fluoride and methanesulfonic acid converted the former sulfoxide to Sp-methoxyphenylcysteine or Sp-hydroxyphenylcysteine in the presence of anisole or phenol, respectively, while the latter sulfoxide resisted the actions of these deprotecting reagents. Thiophenol appears to be useful as a powerful reducing reagent ...