Viable construction of N-methyl cysteine and its use in peptide synthesis

ORGN 144

Erik L. Ruggles, Erik.Ruggles@uvm.edu and Robert J. Hondal, Robert.Hondal@uvm.edu. Department of Biochemistry, University of Vermont, Given Laboratory, 89 Beaumont Ave, Burlington, VT 05405
The cyclocystine subunit (CCS, 1), which results from a disulfide-bond between adjacent cysteine residues, is a rare motif in protein structure and is functionally important to those proteins that posses it. This poster will focus on the construction of N-methyl CCS (4) that requires the large-scale production of Fmoc-protected N-methyl cysteine. While a number of methods exist for the production of α-alkyl N-methyl amino acid derivatives, one finds less literature involving the generation of N-methyl cysteine. Various methods for amino methylation of cysteine, in the presence of acid labile or acid stable sulfhydryl protecting groups, are compared and contrasted.