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Names | |
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IUPAC name (10S)-2-benzoyl-1,3,8,10-tetrahydroxy-9-(4-methoxy-6-oxopyran-2-yl)-5-oxatricyclo[4.3.1.03,8]decan-4-one | |
Other names Vulgamycin | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
PubChem CID | |
CompTox Dashboard (EPA) | |
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Properties | |
C22H20O10 | |
Molar mass | 444.392 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Enterocin and its derivatives are bacteriocins synthesized by the lactic acid bacteria, Enterococcus . This class of polyketide antibiotics are effective against foodborne pathogens including L. monocytogenes, Listeria, and Bacillus. [1] Due to its proteolytic degradability in the gastrointestinal tract, enterocin is used for controlling foodborne pathogens via human consumption. [2]
Enterocin was discovered from soil and marine Streptomyces [3] strains as well as from marine ascidians of Didemnum [4] and it has also been found in a mangrove strains Streptomyces qinglanensis and Salinispora pacifica . [5]
The total synthesis of enterocin has been reported. [6]
Enterocin has a caged, tricyclic, nonaromatic core and its formation undergoes a flavoenzyme (EncM) catalyzed Favorskii-like rearrangement of a poly(beta-carbonyl). [7] Studies done on enterocin have shown that it is biosynthesized from a type II polyketide synthase (PKS) pathway, starting with a structure derived from phenylalanine or activation of benzoic acid followed by the EncM catalyzed rearrangement.
The enzyme EncN catalyzes the ATP-dependent transfer of the benzoate to EncC, the acyl carrier protein. EncC transfers the aromatic unit to EncA-EncB, the ketosynthase in order for malonation via FabD, the malonyl-CoA:ACP transacylase. A Claisen condensation occurs between the benzoyl and malonyl groups and occurs six more times followed by reaction with EncD, a ketoreductase; the intermediate undergoes the EncM catalyzed oxidative rearrangement to form the enterocin tricyclic core. Further reaction with O-methyltransferase, EncK and cytochrome P450 hydroxylase, EncR yields enterocin. [9]