Trimethylacetamidomethyl (Tacm) Group, a New Protecting Group for the Thiol Function of Cysteine

Yoshiaki KISO; Makoto YOSHIDA; Yoichi FUJIWARA; Tooru KOIMURA; Masanori SHIMOKURA; Kenichi AKAJI

doi:10.1248/cpb.38.673

Yoshiaki KISO, Makoto YOSHIDA, Yoichi FUJIWARA, Tooru KOIMURA, Masanori SHIMOKURA, Kenichi AKAJI

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Keywords: cysteine S-protecting group, S-trimethylacetamidomythyl-L-cysteine, peptide synthesis, iodine-oxidation, mercury ion deprotection, S-protected cysteine sulfoxide

JOURNAL FREE ACCESS

1990 Volume 38 Issue 3 Pages 673-675

DOI https://doi.org/10.1248/cpb.38.673

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Abstract

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).

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