Enterocin
Names
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
ChemSpider
InChI=1S/C22H20O10/c1-30-11-7-12(31-14(23)8-11)16-20(27)9-13-18(25)21(16,28)17(22(20,29)19(26)32-13)15(24)10-5-3-2-4-6-10/h2-8,13,16-18,25,27-29H,9H2,1H3/t13?,16?,17?,18-,20?,21?,22?/m0/s1
Key: CTBBEXWJRAPJIZ-LXJDDUSDSA-N
COC1=CC(=O)OC(=C1)C2C3(CC4C(C2(C(C3(C(=O)O4)O)C(=O)C5=CC=CC=C5)O)O)O
Properties
C 22 H 20 O 10
Molar mass
−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Enterocin and its derivatives are bacteriocins synthesized by the lactic acid bacteria, Enterococcus polyketide antibiotics are effective against foodborne pathogens including L. monocytogenes , Listeria ,Bacillus .[ 1] gastrointestinal tract , enterocin is used for controlling foodborne pathogens via human consumption.[ 2]
History
Enterocin was discovered from soil and marine Streptomyces [ 3] Didemnum [ 4] Streptomyces qinglanensis Salinispora pacifica [ 5]
Total synthesis
The total synthesis of enterocin has been reported.[ 6]
Biosynthesis
Enterocin has a caged, tricyclic, nonaromatic core and its formation undergoes a flavoenzyme (EncM) catalyzed Favorskii -like rearrangement of a poly(beta-carbonyl).[ 7] phenylalanine or activation of benzoic acid followed by the EncM catalyzed rearrangement.
Proposed biosynthetic pathway of enterocin.[ 8] 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 -methyltransferasecytochrome P450 hydroxylase, EncR yields enterocin.[ 9]
References
^ Khan H, Flint S, Yu PL (June 2010). "Enterocins in food preservation". International Journal of Food Microbiology . 141 (1– 2): 1– 10. doi :10.1016/j.ijfoodmicro.2010.03.005 . PMID 20399522 . ^ Singh A, Walia D, Batra N (2018-01-01). "Fresh-Cut Fruits: Microbial Degradation and Preservation". Microbial Contamination and Food Degradation . pp. 149– 176. doi :10.1016/B978-0-12-811515-2.00006-8 . ISBN 978-0-12-811515-2 ^ Miyairi N, Sakai H, Konomi T, Imanaka H (March 1976). "Enterocin, a new antibiotic taxonomy, isolation and characterization" . The Journal of Antibiotics . 29 (3): 227– 35. doi :10.7164/antibiotics.29.227 PMID 770404 . ^ Kang H, Jensen PR, Fenical W (1996). "Isolation of Microbial Antibiotics from a Marine Ascidian of the GenusDidemnum" The Journal of Organic Chemistry . 61 (4): 1543– 1546. doi :10.1021/jo951794g . ISSN 0022-3263 . ^ Bonet B, Teufel R, Crüsemann M, Ziemert N, Moore BS (March 2015). "Direct capture and heterologous expression of Salinispora natural product genes for the biosynthesis of enterocin" . Journal of Natural Products . 78 (3): 539– 42. doi :10.1021/np500664q . PMC 4380194 PMID 25382643 . ^ Rizzo A, Trauner D (April 2018). "Toward (-)-Enterocin: An Improved Cuprate Barbier Protocol To Overcome Strain and Sterical Hindrance". Organic Letters . 20 (7): 1841– 1844. doi :10.1021/acs.orglett.8b00353 . PMID 29553746 . ^ Teufel R, Miyanaga A, Michaudel Q, Stull F, Louie G, Noel JP, et al. (November 2013). "Flavin-mediated dual oxidation controls an enzymatic Favorskii-type rearrangement" . Nature . 503 (7477): 552– 556. Bibcode :2013Natur.503..552T . doi :10.1038/nature12643 . PMC 3844076 PMID 24162851 . ^ Rohr J, Hertweck C (2010-01-01). "Type II PKS". In Liu HW, Mander L (eds.). Comprehensive Natural Products II . pp. 227– 303. doi :10.1016/B978-008045382-8.00703-6 . ISBN 9780080453828 ^ Kalaitzis JA, Cheng Q, Thomas PM, Kelleher NL, Moore BS (March 2009). "In vitro biosynthesis of unnatural enterocin and wailupemycin polyketides" . Journal of Natural Products . 72 (3): 469– 72. doi :10.1021/np800598t . PMC 2765504 PMID 19215142 .
