Diperamycin

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Category Antibiotics
Catalog number BBF-01162
CAS 220766-06-3
Molecular Weight 856.96
Molecular Formula C38H46N8O14

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Description

It is produced by the strain of Streptomyces griseoaurantiacus MK393-AF2. It has activity against gram-positive bacteria, including Enterococcus seriolicida and MRSA (MIC is 0.10-0.20 μg/mL). It also strongly inhibits the activity of L1210, P388, LS-180, KB, HeLaS3, Meth A and B16-BL6 (IC50 is 0.009-0.098 μg/mL).

Specification

Synonyms GNF-Pf-91; N-[6,18-dihydroxy-7-(methoxymethyl)-19,22-dimethyl-5,8,11,17,20,24-hexaoxodocosahydro-13H,22H-dipyridazino[6,1-f:6',1'-o][1,4,7,10,13,16]oxapentaazacyclononadecin-23-yl]-2-(5-hexyl-2-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)-2-hydroxypropanamide
IUPAC Name N-[7,21-dihydroxy-6-(methoxymethyl)-17,20-dimethyl-2,5,8,15,19,22-hexaoxo-18-oxa-1,4,7,13,14,21,27-heptazatricyclo[21.4.0.09,14]heptacosan-16-yl]-2-(5-hexyl-2-hydroxy-6-methyloxan-2-yl)-2-hydroxypropanamide
Canonical SMILES CCCCCCC1CCC(OC1C)(C(C)(C(=O)NC2C(OC(=O)C(N(C(=O)C3CCCNN3C(=O)CNC(=O)C(N(C(=O)C4CCCNN4C2=O)O)COC)O)C)C)O)O
InChI InChI=1S/C38H64N8O14/c1-7-8-9-10-13-25-16-17-38(55,60-23(25)3)37(5,54)36(53)42-30-24(4)59-35(52)22(2)45(56)32(49)26-14-11-18-40-43(26)29(47)20-39-31(48)28(21-58-6)46(57)33(50)27-15-12-19-41-44(27)34(30)51/h22-28,30,40-41,54-57H,7-21H2,1-6H3,(H,39,48)(H,42,53)
InChI Key IHQIMVZJVJTKSV-UHFFFAOYSA-N

Properties

Appearance White Powder
Antibiotic Activity Spectrum Gram-positive bacteria; Neoplastics (Tumor)
Melting Point 152-154 °C (dec.)
Solubility Soluble in Methanol

Reference Reading

1. Diperamycin, a new antimicrobial antibiotic produced by Streptomyces griseoaurantiacus MK393-AF2. I. Taxonomy, fermentation, isolation, physico-chemical properties and biological activities
N Matsumoto, I Momose, M Umekita, N Kinoshita, M Chino, H Iinuma, T Sawa, M Hamada, T Takeuchi J Antibiot (Tokyo). 1998 Dec;51(12):1087-92. doi: 10.7164/antibiotics.51.1087.
Antibacterial antibiotics, diperamycin (1) was produced in the culture broth of Streptomyces griseoaurantiacus MK393-AF2. Various spectroscopic analyses of 1 suggested that 1 belonged to a member of cyclic hexadepsipeptide antibiotic. Antibiotic 1 had potent inhibitory activity against various Gram-positive bacteria including Enterococcus seriolicida and methicillin-resistant Staphylococcus aureus.

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