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Actaplanin (A4696), a new complex of broad spectrum Gram-positive antibiotics is produced by Actinoplanes inissouriensis. High performance liquid chromatography was used to show that this complex is composed of several actaplanins.Hydrolytic experiments with actaplanins A, B,, B., B3, C, and G showed that these actaplanins were composed of the same peptide core, an amino sugar and varying amounts of glucose, mannose and rhamnose. The neutral sugar content was determined for each actaplanin. A bioautographic study of aglycone formation during hydrolysis of the actaplanin complex showed that within a short time a simple mixture of two antimicrobially active hydrolysis products was obtained. These substances retained the antimicrobial spectrum and a high percentage of the antibiotic activity of the parent actaplanin complex.Methanolysis of the actaplanin complex as well as the individual actaplanins resulted in the selective loss of the neutral sugar moieties and the isolation of actaplanin T(pseudo)-aglyconethe core peptide which still retained an amino sugar group. The 1H NMR spectrum of this substance indicated a similarity to many features of ristocetin ?Ir aglycone. Hydrolytic studies showed that the amino sugar present in actaplanin was identical with L-ristosamine. It is concluded that the aglycone of actaplanin is a complex peptide composed of aromatic amino acids, and that the actaplanins each possess this aglycone and L-ristosamine but are differentiated by their neutral sugar composition. Actaplanin (A4696)**, a new complex of glycopeptide antibiotics produced by Actinoplanes missouriensis (ATCC 23342), exhibits strong inhibitory activity against a broad spectrum of Gram-positive bacteria.The isolation of the actaplanin complex showed that actaplanin was composed of several closely related glycopeptide components (hereafter referred to as actaplanins) by their chromatographic behavior.Several recent structural studies of glycopeptide antibiotics1~5) have shown that these antibiotics appear to hold several chemical features in common. Typically, glycopeptides give rise to an "aglycone," neutral sugars"') and an amino sugar upon mild hydrolysis',1-12). Furthermore, the aglycone is a complex peptide which retains the same amino acids present in the parent after total hydrolysis and also some of the antimicrobial activity of the parent.The purpose of the present study was to determine the general chemical characteristics of the actaplanin complex and to relate the differences and the similarities it bears to known members of its class". The chemical relationship between the various actaplanins has also been determined.

The structures of some of the minor factors of the nebramycin complex of antibiotics are elucidated through a combination of physical and chemical methods.

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offers this solution:16 5.203 (H-5), 3.745, 3.613 (H-4, /gem = (15) We are grateful to Dr. Richard S. Egan for this spectrum and solution. The ABX spectrum was calculated using laocn3 [S. Castellano and A. A. Bothner-by, J. Chem. Phys., 41, 3853 (1964) ], as modified by Mr. W. C. Bass, Abbott Laboratories.

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