85550-10-3

Upstream product

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

Downstream Products

• 85482-80-0 S-benzoyl-N-benzyloxycarbonyl-threo-3-methyl-D-cysteine methyl ester 
• 112194-82-8 (αR,βR)-N^α-carbobenzoxy-1,β-dimethyltryptophan 
• 128984-33-8 (2R,3R)-2-Benzyloxycarbonylamino-3-(1-ethyl-1H-indol-3-yl)-butyric acid 
• 128984-36-1 (2R,3R)-2-Benzyloxycarbonylamino-3-(1,5-dimethyl-1H-indol-3-yl)-butyric acid 
• 128984-37-2 (2R,3R)-2-Benzyloxycarbonylamino-3-(5-fluoro-1-methyl-1H-indol-3-yl)-butyric acid 
• 128984-34-9 (2R,3R)-2-Benzyloxycarbonylamino-3-(5-methoxy-1-methyl-1H-indol-3-yl)-butyric acid 
• 425399-95-7 2-benzyloxycarbonylamino-3-benzylsulfanyl-butyric acid methyl ester 
• 858669-60-0 (2S,3S)-2-Benzyloxycarbonylamino-3-tritylsulfanyl-butyric acid methyl ester 
• 858669-61-1 (2S,3S)-N-benzyloxycarbonyl-3-methylcysteine methyl ester 
• 858669-59-7 (2S,3S)-2-Benzyloxycarbonylamino-3-(4-methoxy-benzylsulfanyl)-butyric acid methyl ester 
• 103958-66-3 (αR,βR)-N-benzyloxycarbonyl-1,β-dimethyltryptophane methyl ester 
• 60027-61-4 methyl (2Z)-2-(N-benzyloxycarbonylamino)but-2-enoate 

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]

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