Boc-S-methylbenzyl-(S)-2-amino-6-mercaptohexanoic acid: Preparation and application to the synthesis of a large cyclic disulfide peptide

Article abstract of DOI:10.1016/0040-4039(95)00590-9

A derivative of 2-amino-6-mercaptohexanoic acid (Amh) suitable for Boc solid phase synthesis has been prepared by conversion of the ε-NH₂ group of lysine into a 4-methylbenzyl thioether. The derivative has been used in the synthesis of a 22-residue peptide with a 62-atom cyclic disulfide. Amh(Meb) is stable to acidolysis but can be conveniently deprotected, with simultaneous disulfide formation, by treatment with diphenyl sulfoxide and trichloromethylsilane.