Boromycin

Title: Boromycin
CAS Registry Number: 34524-20-4
Molecular Formula: C45H74BNO15
Molecular Weight: 879.88
Percent Composition: C 61.43%, H 8.48%, B 1.23%, N 1.59%, O 27.28%
Literature References: Antibiotic produced by Streptomyces antibioticus ETH 28829: Hütter et al., Helv. Chim. Acta 50, 1533 (1967). The first known natural product in which boron has been found. It is a complex of boric acid with a tetradentate organic complexing agent and yields D-valine, boric acid and a polyhydroxy macrolide-type compound upon hydrolysis. Structure: Dunitz et al., ibid. 54, 1709 (1971). Mechanism of action studies: Pache, Zähner, Arch. Mikrobiol. 67, 156 (1969). Activity as a coccidiostat: Miller, Burg, US 3864479 (1975 to Merck & Co.). Biosynthesis: T. S. S. Chen et al., J. Org. Chem. 46, 2661 (1981). Partial synthesis: M. A. Avery et al., Tetrahedron Lett. 22, 3123 (1981). Synthesis of C-3¢ to C-17¢: S. Hanessian et al., J. Am. Chem. Soc. 103, 6243 (1981); of C-3 to C-17: eidem, Can. J. Chem. 61, 634 (1983); of C-1 to C-17: J. D. White et al., J. Am. Chem. Soc. 105, 6517 (1983). Total synthesis: eidem, ibid. 111, 790 (1989). Review: Pache in Antibiotics vol. 3, J. W. Corcoran, F. E. Hahn, Eds. (Springer-Verlag, New York, 1975) pp 585-587.
Properties: Colorless crystals from methanol, mp 223-228° (dec). [a]D +63.5° (c = 0.55 in CHCl3). No uv absorption between 210 and 400 nm. LD50 orally in mice: 180 mg/kg (Hütter).
Melting point: mp 223-228° (dec)
Optical Rotation: [a]D +63.5° (c = 0.55 in CHCl3)
Toxicity data: LD50 orally in mice: 180 mg/kg (Hütter)
Boron Carbide Boron Monoxide Boron Nitride Boron Tribromide Boron Trichloride

Boromycin
Boromycin.png
Systematic (IUPAC) name
[1-{(1R)-1-[(1R,2R,5S,6R,8R,12R,14S,17R,18R,22S,24Z,28S,30S,33R)-12,28-dihydroxy-1,2,18,19-tetra(hydroxy-kO)-6,13,13,17,29,29,33-heptamethyl-3,20-dioxo-4,7,21,34,35-pentaoxatetracyclo[28.3.1.15,8.114,
Clinical data
Legal status -only (US)
Identifiers
CAS number 34524-20-4
ATC code None
PubChem CID 6436027
ChemSpider 16735705 YesY
Chemical data
Formula C45H74BNO15 
Mol. mass 879.878 g/mol
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Boromycin is a bacteriocidal polyether-macrolide antibiotic. It was initially isolated from the Streptomyces strain Streptomyces antibioticus, and is notable for being the first natural product found to contain the element boron. It is effective against most Gram-positive bacteria, but is ineffective against Gram-negative bacteria. Boromycin kills bacteria by negatively affecting the cytoplasmic membrane, resulting in the loss of potassium ions from the cell.