N-Boc-S-methyl-L-cysteine (CAS 16947-80-1)

N-Boc-S-methyl-L-cysteine is a modified amino acid, where the natural amino acid L-cysteine is chemically altered by the addition of a tert-butoxycarbonyl (Boc) protecting group on the nitrogen atom and a methyl group on the sulfur atom. The Boc group is a common protecting group used in peptide synthesis to prevent unwanted reactions at the amine group during the coupling of amino acids. The primary mechanism of action of N-Boc-S-methyl-L-cysteine involves its use as a building block in the synthesis of peptides and modified proteins. The Boc group protects the amine functionality from reacting prematurely, which is crucial in stepwise peptide synthesis where amino acids are added one at a time. The S-methyl group on the cysteine side chain increases the hydrophobicity and stability of the amino acid, preventing oxidation of the thiol group that would normally form disulfide bonds. In research, N-Boc-S-methyl-L-cysteine is utilized to study protein structure and function by allowing for the site-specific introduction of modified amino acids into peptides and proteins. This can be particularly useful in understanding the role of cysteine residues in protein folding, stability, and function, as the methylated thiol can mimic the behavior of cysteine in a more controlled manner without engaging in disulfide bond formation. Furthermore, this compound is used in the development of novel peptides and small molecules with enhanced pharmacological properties. By incorporating N-Boc-S-methyl-L-cysteine into peptides, researchers can increase the lipophilicity and membrane permeability of the molecule, making it more suitable for potential therapeutic applications where control of protein-protein interactions is desired.