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boromycin

Structure via PubChem · Public domain (PubChem)

EntityQ4946240· pop 7· linked from 113 articles

Boromycin is a bacteriocidal polyether-macrolide antibiotic. It was initially isolated from the 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. Boromycin has not been approved as a drug for medical use.

Chemical data

Formula
C45H74BNO15
Molecular weight
879.9 g/mol
IUPAC name
[(2R)-1-[(1R)-1-[(1R,5S,7E,11S,13S,16R,17R,24S,25R,27R,31R,33S,36R)-11,31-dihydroxy-12,12,16,25,32,32,36-heptamethyl-3,22-dioxo-4,18,20,23,26,37,38,40,41-nonaoxa-19-boranuidaheptacyclo[17.17.1.11,33.12,19.113,17.124,27.017,21]hentetracont-7-en-5-yl]ethoxy]-3-methyl-1-oxobutan-2-yl]azanium
SMILES
[B-]123OC4C(=O)O[C@@H](C/C=C/CC[C@@H](C([C@@H]5CC[C@H]([C@@](O1)(O5)C(O2)C(=O)O[C@H]6C[C@@H](CCC[C@H](C([C@@H]7CC[C@H]([C@@]4(O3)O7)C)(C)C)O)O[C@@H]6C)C)(C)C)O)[C@@H](C)OC(=O)[C@@H](C(C)C)[NH3+]
InChIKey
OOBFYEMEQCZLJL-XURNZCJASA-O
Polar surface area
212 Ų
H-bond donors
3
H-bond acceptors
16
Formal charge
0

via PubChem

Wikidata facts

Mass
879.5151510680001
Show 3 more facts
chemical formula
C₄₅H₇₄BNO₁₅
canonical SMILES
[B-]123OC4C(=O)OC(CC=CCCC(C(C5CCC(C(O1)(O5)C(O2)C(=O)OC6CC(CCCC(C(C7CCC(C4(O3)O7)C)(C)C)O)OC6C)C)(C)C)O)C(C)OC(=O)C(C(C)C)[NH3+]
isomeric SMILES
CC(C)[C@@H]([NH3+])C(=O)O[C@H](C)[C@@H]1C/C=C/CC[C@H](O)C(C)(C)[C@@H]2CC[C@@H](C)[C@]3(O2)O[B-]24OC(C(=O)O1)[C@@]1(O[C@@H](CC[C@H]1C)C(C)(C)[C@H](O)CCC[C@@H]1C[C@H](OC(=O)C3O2)[C@@H](C)O1)O4

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~8 min read

Encyclopedic overview

7 sections
Contents
  • Discovery
  • General information
  • Research
  • Anti-HIV activity
  • Anti-plasmodium activity
  • Activity against intracellular protozoal parasites
  • References

Boromycin is a bacteriocidal polyether-macrolide antibiotic. It was initially isolated from the 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. Boromycin has not been approved as a drug for medical use.

==Discovery== Boromycin was discovered by the scholars of the Institute for Special Botany and Organic Chemical Laboratories at the Swiss Federal Institute of Technology, Zurich, Switzerland, who, in 1967, published a study in as an article called "Metabolic products of microorganisms" in the Helvetica Chimica Acta journal. In this article, the authors described that a new strain of Streptomyces antibioticus produces a novel antibiotic which was the first boron-containing organic compound found in nature. The authors called this new compound boromycin and characterized it as a complex of boric acid with a tetradentate organic complexing agent that yields by hydrolysis D-valine, boric acid, and a polyhydroxy compound of macrolide type.

Excerpted from Wikipedia’s “boromycin” article, available under the CC BY-SA 4.0 licence.

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