85482-79-7Relevant academic research and scientific papers
Scalable synthesis of orthogonally protected β-methyllanthionines by indium(III)-mediated ring opening of aziridines
Li, Ziran,Gentry, Zachary,Murphy, Brennan,Vannieuwenhze, Michael S.
supporting information, p. 2200 - 2203 (2019/03/26)
Lantibiotics are a class of peptide antibiotics with activity against most Gram-positive bacteria. Lanthionine (Lan) and β-MeLan are unusual thioether-bridged, non-proteinogenic amino acids, which are characteristic features of lantibiotics. In this paper, we report the facile stereoselective synthesis of β-methyllanthionines with orthogonal protection by nucleophilic ring opening of aziridines. This method leads to an expedient access to β-methyllanthionines and allows production of over 30 g of β-methyllanthionine in a single batch.
Versatile and stereoselective syntheses of orthogonally protected β-methylcysteine and β-methyllanthionine
Narayan, Radha S.,VanNieuwenhze, Michael S.
, p. 2655 - 2658 (2007/10/03)
(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
Synthesis of threo-3-Methylcysteine from Threonine
Wakamiya, Tateaki,Shimbo, Kuniaki,Shiba, Tetsuo,Nakajima, Kiichiro,Neya, Masahiro,Okawa, Kenji
, p. 3878 - 3881 (2007/10/02)
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
