85482-83-3

Upstream product

• 76-83-5 trityl chloride 
• 124-63-0 methanesulfonyl chloride 
• 85482-79-7 N-trityl-D-threonine methyl ester 

Downstream Products

• 85550-09-0 (2R,3R)-1-trityl-3-methyl-2-aziridinecarboxylic acid methyl ester 
• 85482-80-0 S-benzoyl-N-benzyloxycarbonyl-threo-3-methyl-D-cysteine methyl ester 
• 858669-61-1 (2S,3S)-N-benzyloxycarbonyl-3-methylcysteine methyl ester 
• 425399-95-7 2-benzyloxycarbonylamino-3-benzylsulfanyl-butyric acid methyl ester 
• 85550-10-3 (2R,3R)-1-benzyloxycarbonyl-3-methyl-2-aziridinecarboxylic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of threo-3-Methylcysteine from Threonine

threo-3-Methyl-D-cysteine as a moiety of β-methyllanthionine in the peptide antibiotic nisin was synthesized stereospecifically.The reaction of (2R,3R)-3-methyl-2-aziridinecarboxylic acid derivative prepared from D-threonine with thiobenzoic acid gave the

Biomimetic stereoselective formation of methyllanthionine.

Fmoc-(2R,3S)-3-methyl-Se-phenylselenocysteine was used for the synthesis of dehydrobutyrine (Dhb)-containing peptides. Biomimetic cyclization via Michael addition of Cys to a Dhb yielded the B-ring of the lantibiotic subtilin as a single diastereomer. The methyllanthionine product was shown to have the natural configuration by preparation of the authentic stereoisomer. The formation of a single isomer suggests that the prepeptide has a strong intrinsic preference for the stereochemistry observed in lantibiotics. [reaction: see text]