title: Regioselective formation of multiple disulfide bonds with the aid of postsynthetic S-tritylation.
abstract: Disulfide bond formation performed in solution with the tert-butylthio (StBu) group was accomplished using a free peptide having only the sulfhydryl groups of Cys protected with the aid of postsynthetic S-tritylation. This facilitated removal of the StBu group with subsequent disulfide formation without any difficulty. This strategy using the StBu group in combination with the widely used acetamidomethyl (Acm), 4-methylbenzyl/4-methoxybenzyl (Meb/Mob), and trityl (Trt) groups enables reliable and regioselective synthesis of multicystine peptides.
authors: †Peptide Institute, Inc., Ibaraki, Osaka 567-0085, Japan.
authors: Masayoshi
authors: M
authors: Mochizuki
authors: †Peptide Institute, Inc., Ibaraki, Osaka 567-0085, Japan.
authors: Shugo
authors: S
authors: Tsuda
authors: †Peptide Institute, Inc., Ibaraki, Osaka 567-0085, Japan.
authors: Kyoko
authors: K
authors: Tanimura
authors: †Peptide Institute, Inc., Ibaraki, Osaka 567-0085, Japan.|‡Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan.
authors: Yuji
authors: Y
authors: Nishiuchi
mesh_terms: D000595:Amino Acid Sequence; D001593:Benzyl Compounds / Q000737:chemistry*; D002073:Butanes / Q000737:chemistry*; D003545:Cysteine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D004220:Disulfides / Q000737:chemistry*; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D013438:Sulfhydryl Compounds
chemical_list: D001593:Benzyl Compounds; D002073:Butanes; D004220:Disulfides; D010455:Peptides; D013438:Sulfhydryl Compounds; D003545:Cysteine