Trimethylacetamidomethyl (Tacm) group, a new protecting group for the thiol function of cysteine

Article abstract of DOI:10.1248/cpb.38.673

S-Trimethylacetamidomethyl-L-cysteine [Cys(Tacm)] was easily prepared from N-hydroxymethyltrimethyl-acetamide and L-cysteine in trifluoroacetic acid. The S-Tacm group is stable to HF, but cleavable with mercury(II) acetate in trifluoroacetic acid or iodine in aqueous acetic acid. Cys(Tacm) is less susceptible to sulfoxide formation than three related groups, i.e., acetamidomethyl (Acm), benzamidomethyl (Bam) and (2-oxo-1-pyrrolidinyl)methyl (Pym).

Full text of DOI:10.1248/cpb.38.673

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