Antibiotic A-269A

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Antibiotic A-269A
Category Antibiotics
Catalog number BBF-03035
CAS 38621-52-2
Molecular Weight 459.46
Molecular Formula C17H29N7O8

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Description

It is a streptomycin antibiotic produced by the strain of Streptomyces sp. No. A-269. It mainly has the activity against gram-negative bacteria including Escherichia coli and common proteus with MIC (μg/mL) of 1 and 5, respectively.

Specification

Synonyms Antibiotic 6241B; Antibiotic SF 701; Antibiotic LL-BL 136; A-269A; 4H-Imidazo(4,5-c)pyridin-4-one, 1,3a,5,6,7,7a-hexahydro-2-((4-O-(aminocarbonyl)-2-deoxy-2-(methyl((methylamino)acetyl)amino)-beta-D-gulopyranoxyl)amino)-7-hydroxy-, (3aS-(3a-alpha,7-alpha,7a-beta))-
IUPAC Name [4-hydroxy-2-(hydroxymethyl)-6-[(7-hydroxy-4-oxo-1,3a,5,6,7,7a-hexahydroimidazo[4,5-c]pyridin-2-yl)amino]-5-[methyl-[2-(methylamino)acetyl]amino]oxan-3-yl] carbamate
Canonical SMILES CNCC(=O)N(C)C1C(C(C(OC1NC2=NC3C(N2)C(CNC3=O)O)CO)OC(=O)N)O
InChI InChI=1S/C17H29N7O8/c1-19-4-8(27)24(2)11-12(28)13(32-16(18)30)7(5-25)31-15(11)23-17-21-9-6(26)3-20-14(29)10(9)22-17/h6-7,9-13,15,19,25-26,28H,3-5H2,1-2H3,(H2,18,30)(H,20,29)(H2,21,22,23)
InChI Key UVPMSKRAZBXYRJ-UHFFFAOYSA-N

Properties

Appearance White Amorphous Powder
Antibiotic Activity Spectrum Gram-negative bacteria
Boiling Point 775.3±70.0°C at 760 mmHg
Melting Point 192-194°C (dec.)
Density 1.86 g/cm3
Solubility Soluble in Water

Reference Reading

1. A streptothricin-like antibiotic mixture, A-269A (and A-269A')
Y Kido, T Furuie, K Suzuki, K Sakamoto, Y Yokoyama, M Uyeda, J Kinjyo, S Yahara, T Nohara, M Shibata J Antibiot (Tokyo). 1987 Dec;40(12):1698-706. doi: 10.7164/antibiotics.40.1698.
A streptothricin-like antibiotic, A-269A (referred to as A-269A hereafter) was isolated from the culture broth of Streptomyces sp., strain No. A-269. In this paper, the characterization of the producer, and the production, isolation, physico-chemical properties and biological properties of A-269A are reported. The structure of the antibiotic was also examined by 1H NMR, 13C NMR and fast atom bombardment mass spectra studies. From the spectroscopic data, A-269A was assumed to be a mixture of antibiotic LL-BL 136 and an isomeric compound in which the carbamoyl group is substituted on C-12' hydroxyl instead of C-10 hydroxyl.

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