425399-95-7

Upstream product

• 85482-83-3 (2R,3S)-3-Methanesulfonyloxy-2-(trityl-amino)-butyric acid methyl ester 
• 85482-79-7 N-trityl-D-threonine methyl ester 
• 85550-09-0 (2R,3R)-1-trityl-3-methyl-2-aziridinecarboxylic acid methyl ester 
• 85551-31-1 (2R,3R)-3-MeAzyOMe 
• 501-53-1 benzyl chloroformate 
• 85550-10-3 (2R,3R)-1-benzyloxycarbonyl-3-methyl-2-aziridinecarboxylic acid methyl ester 
• 100-53-8 phenylmethanethiol 

Relevant academic research and scientific papers

Versatile and stereoselective syntheses of orthogonally protected β-methylcysteine and β-methyllanthionine

(Chemical Equation Presented) Lantibiotics are a class of lanthionine (and/or β-methyllanthionine)-containing peptides with antibioitic activity against Gram-positive bacteria. As part of our research effort directed toward the synthesis and mechanistic s

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]