New glycopeptide antibiotics: II. The isolation and structures of chloroorienticins.

The Journal of Antibiotics
1988.0

Abstract

During screening studies to find new glycopeptide antibiotics, we elucidated the structure of orienticins which have excellent antibacterial activity against methicillin-resistant Staphylococcus aureus equivalent to vancomycin. We isolated new vancomycin-type antibiotics, chloroorienticins (including A, B, C, D, and E), from the fermentation broth of Amycolatopsis orientalis (Nocardia orientalis) PA-45052. In this communication paper, we report the isolation of chloroorienticins and their structures. The chloroorienticin complex was separated by MCI gel CHP20P (Mitsubishi Chemical Industries Limited) column and Packed column RQ-2 (C18, Fuji gel) chromatography. The structures of these molecules were elucidated by ¹H, ¹³C NMR and mass spectroscopies and confirmed by chemical transformations or degradations. Chloroorienticin A is very similar to orienticin A but has Cl substitutions at positions A-3 and C-5 (like vancomycin), which was confirmed by selective hydrogenolysis to orienticin A and hydrolysis to the aglycone of vancomycin and identification of sugar parts (D-glucose and L-4-epi-vancosamine). Chloroorienticin B, one of the major components, lacks one of the 4-epi-vancosamine units from chloroorienticin A and was identified from the products of partial hydrolysis of chloroorienticin A. Chloroorienticin C, a major component, lacks D-glucose from chloroorienticin B. Physico-chemical properties such as specific rotation ([α]ₙ), elemental analysis, and molecular formulas of chloroorienticins A-E are also described.

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