N-alpha-(9-Fluorenylmethyloxycarbonyl)-S-(4,4'-dimethylsulfinylbenzhydryl)-L-cysteine

Msbh is a safety-catch cysteine protecting group, which expands the capabilities of synthetic strategies for the regioselective formation of disulfide bonds in cysteine-rich peptides. The MSBH protecting group is stable to conditions applied in both Boc and Fmoc chemistry. By reduction to the methyl thioether with NH4I/dimethylsulfide in TFA it becomes cleavable under acid conditions and will instantly be removed. References: Total Synthesis of Human Hepcidin through Regioselective Disulfide- Bond Formation by using the Safety-Catch Cysteine Protecting Group 4,4'-Dimethylsulfinylbenzhydryl; Zoltan Dekan, Mehdi Mobli, Michael W. Pennington, Eileen Fung, Elizabeta Nemeth, and Paul F. Alewood; Angew. Chem. Int. Ed. 2014; 53: 2931-2934. DOI: 10.1002/anie.201310103. J. M. Samanen, E. Brandeis; J. Org. Chem. 1988; 53: 561-569. M. Patek, M. Lebl; Tetrahedron Lett. 1991; 32: 3891-3894. T. Kimura, T. Fukui, S. Tanaka, K. Akaji, Y. Kiso; Chem. Pharm. Bull. 1997; 45: 18-26. S. Thennarasu, C. F. Liu; Tetrahedron Lett. 2010; 51: 3218-3220.