Department of Chemistry , Indiana University , 800 East Kirkwood Avenue , Bloomington , Indiana 47405-7102 , United States.
Org Lett. 2019 Apr 5;21(7):2200-2203. doi: 10.1021/acs.orglett.9b00125. Epub 2019 Mar 11.
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.
类细菌素是一类具有抗大多数革兰氏阳性菌活性的肽类抗生素。硫醚桥接的非蛋白氨基酸 Lanthionine (Lan) 和 β-MeLan 是类细菌素的特征性结构。本文报道了通过氮杂环丙烷的亲核开环反应,以立体选择性方式对 β-甲硫氨酸进行正交保护的简便合成方法。该方法可方便地获得 β-甲硫氨酸,并可在单个批次中生产超过 30 克的 β-甲硫氨酸。