A NEW THIOL PROTECTING TRIMETHYLACETAMIDOMETHYL GROUP. SYNTHESIS OF A NEW PORCINE BRAIN NATRIURETIC PEPTIDE USING THE S-TRIMETHYLACETAMIDOMETHYL-CYSTEINE
The S-trimethylacetamidomethyl-cysteine , which can be easily prepared without any serious side reaction, was stable to acidic and alkaline conditions, and readily converted to cystine by iodine oxidation.This new Cys(Tacm)derivative is successfully applied to the conventional solution synthesis of a new porcine brain natriuretic peptide.
Trimethylacetamidomethyl (Tacm) group, a new protecting group for the thiol function of cysteine
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).
Kiso,Yoshida,Fujiwara,Kimura,Shimokura,Akaji
p. 673 - 675
(2007/10/02)
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