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Scalable Synthesis of Orthogonally Protected ?-Methyllanthionines by Indium(III)-Mediated Ring Opening of Aziridines.

ABSTRACT: Lantibiotics are a class of peptide antibiotics with activity against most Gram-positive bacteria. Lanthionine (Lan) and ?-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 ?-methyllanthionines with orthogonal protection by nucleophilic ring opening of aziridines. This method leads to an expedient access to ?-methyllanthionines and allows production of over 30 g of ?-methyllanthionine in a single batch.

SUBMITTER: Li Z

PROVIDER: S-EPMC6542561 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature

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Scalable Synthesis of Orthogonally Protected β-Methyllanthionines by Indium(III)-Mediated Ring Opening of Aziridines.

Li Ziran Z Gentry Zachary Z Murphy Brennan B VanNieuwenhze Michael S MS

Organic letters 20190311 7

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 o ...[more]

PMID: 30855974

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