Fosfadecin

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Category Antibiotics
Catalog number BBF-01436
CAS 120909-50-4
Molecular Weight 467.27
Molecular Formula C13H19N5O10P2

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Description

Fosfadecin is produced by the strain of Pseudomonas fluorescens PK-5. It has a weak antibacterial activity, the ED50 of Escherichia coli O-111 and Staphylococcus aureus 308A-1 was 800mg/kg and 566mg/kg (mice, oral).

Specification

Synonyms Tan 930; 9-[5-O-(Hydroxy{[hydroxy(3-methyloxiran-2-yl)phosphoryl]oxy}phosphoryl)pentofuranosyl]-9H-purin-6-amine
IUPAC Name [[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-(3-methyloxiran-2-yl)phosphinic acid
Canonical SMILES CC1C(O1)P(=O)(O)OP(=O)(O)OCC2C(C(C(O2)N3C=NC4=C(N=CN=C43)N)O)O
InChI InChI=1S/C13H19N5O10P2/c1-5-13(26-5)29(21,22)28-30(23,24)25-2-6-8(19)9(20)12(27-6)18-4-17-7-10(14)15-3-16-11(7)18/h3-6,8-9,12-13,19-20H,2H2,1H3,(H,21,22)(H,23,24)(H2,14,15,16)
InChI Key XLKKASKVRUMAHE-UHFFFAOYSA-N

Properties

Appearance White Powder
Antibiotic Activity Spectrum fungi
Boiling Point 840.9°C at 760 mmHg
Density 2.34 g/cm3

Reference Reading

1. Fosfadecin and fosfocytocin, new nucleotide antibiotics produced by bacteria
N Katayama, S Tsubotani, Y Nozaki, S Harada, H Ono J Antibiot (Tokyo). 1990 Mar;43(3):238-46. doi: 10.7164/antibiotics.43.238.
Two new nucleotide antibiotics, fosfadecin and fosfocytocin, have been isolated from the culture filtrates of Pseudomonas viridiflava PK-5 and Pseudomonas fluorescens PK-52, respectively. These antibiotics were purified by column chromatographies using adsorption, gel filtration and ion exchange resins. On the basis of the spectroscopic and degradation studies, the chemical structures of fosfadecin and fosfocytocin were determined. These antibiotics were either enzymatically or chemically hydrolyzed to generate fosfomycin and a new antibiotic, fosfoxacin, which are also produced in the culture filtrates. They showed antibacterial activity against Gram-positive and Gram-negative bacteria. The antibacterial activity of these nucleotide antibiotics was weaker than that of fosfomycin and fosfoxacin.

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