By combination of chemical, XKand 13C NMR,and mass spectrometric studies, the structures of the three components of the antibiotic ramoplanin (A-16686), produced by Actinoplanes sp. ATCC 33076, have been elucidated. All the components have structures formed by a commondepsipeptide skeleton carrying a dimannosyl group and are differentiated by the presence of various acylamide moieties, derived from C8, C9 and C10 fatty acids. A-16686,n an antibiotic produced by Actinoplanes sp. ATCC33076,1} is active against aerobic and anaerobic Gram-positive bacteria, including methicillin-resistant Staphylococci and bacteria resistant to ampicillin and/or erythromycin.2~5) In particular, it is very active against a series of clinical isolates of strains of Propionibacterium acnes.® Preliminary physico-chemical characterization^indicated that A-16686 is formed by a peptidic core carrying two D-mannose units. Reversed-phase high pressure liquid chromatography (HPLC) showed at an early stage that it consists of three related factors, designated Al, A2 and A3, as shown in Fig. 1. Single fac-Factor F
Actinoplanes sp. ATCC 33076 is a new strain that was found to produce an antibiotic, designated A-16686, which is a complex of three closely-related polypeptides containing chlorinated phenyl moieties and D-mannose. Both the complex and the single fractions possess a good activity against Gram-positive bacteria. A-16686 specifically inhibits the synthesis of the bacterial cell wall. Culture media* Medium No. 2 (yeast extract-malt agar)
Homonuclear 2D NMRspectroscopy double quantum filter correlation spectroscopy (DQF-COSY),relayed-COSY, nuclear Overhauser enhancement spectroscopy (NOESY),and DQF-relayed-NOESY) allowed the complete determination of the core depsipeptide of antibiotic ramoplanin (A-16686). In particular, the DQF-relayed-NOESYexperiments were essential in assigning the single signals close to the diagonal.
Ramoplanin (A-16686) is a new antibioticproduced by Actinoplanes sp. ATCC33076. The taxonomy of the producing organism, the production, isolation and properties of the antibiotic were previously described.1'^The antibiotic was shown to consist of three components designated Al, Fig. 1. m NMR spectrum (500 MHz) ofA-16686 factor A2 in H2O -DMSO (4: 1) at pH 4.6, 40°C.
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