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MedKoo Cat#: 585394 | Name: Enterocin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Enterocin is an antibiotic isolated from Streptomyces candidus var. enterostaticus WS-8096 and Streptomyces viridochromogenes M-127.

Chemical Structure

Enterocin
Enterocin
CAS#59678-46-5

Theoretical Analysis

MedKoo Cat#: 585394

Name: Enterocin

CAS#: 59678-46-5

Chemical Formula: C22H20O10

Exact Mass: 444.1056

Molecular Weight: 444.39

Elemental Analysis: C, 59.46; H, 4.54; O, 36.00

Price and Availability

Size Price Availability Quantity
1mg USD 450.00 2 Weeks
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Related CAS #
No Data
Synonym
Enterocin; Vulgamycin; (-)-Enterocin
IUPAC/Chemical Name
3,6-Methanocyclopenta(c)pyran-1(3H)-one, 7-benzoylhexahydro-4a,6,7a,8-tetrahydroxy-5-(4-methoxy-2-oxo-2H-pyran-6-yl)-, (3R,4aR,5S,6S,7S,7aS,8R)-
InChi Key
CTBBEXWJRAPJIZ-VHPBLNRZSA-N
InChi Code
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-/m1/s1
SMILES Code
O=C1[C@@]2(O)[C@@]([C@@H](C(O3)=CC(OC)=CC3=O)[C@]4(O)[C@@H]2C(C5=CC=CC=C5)=O)(O)C[C@@]([C@H]4O)([H])O1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 444.39 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Ankaiah D, Palanichamy E, Antonyraj CB, Ayyanna R, Perumal V, Ahamed SIB, Arul V. Cloning, overexpression, purification of bacteriocin enterocin-B and structural analysis, interaction determination of enterocin-A, B against pathogenic bacteria and human cancer cells. Int J Biol Macromol. 2018 Sep;116:502-512. doi: 10.1016/j.ijbiomac.2018.05.002. Epub 2018 May 2. PubMed PMID: 29729340. 2: Qiao X, Du R, Wang Y, Han Y, Zhou Z. Purification, characterization and mode of action of enterocin, a novel bacteriocin produced by Enterococcus faecium TJUQ1. Int J Biol Macromol. 2019 Dec 14;144:151-159. doi: 10.1016/j.ijbiomac.2019.12.090. [Epub ahead of print] PubMed PMID: 31846663. 3: Lauková A, Styková E, Kubašová I, Gancarčíková S, Plachá I, Mudroňová D, Kandričáková A, Miltko R, Belzecki G, Valocký I, Strompfová V. Enterocin M and its Beneficial Effects in Horses-a Pilot Experiment. Probiotics Antimicrob Proteins. 2018 Sep;10(3):420-426. doi: 10.1007/s12602-018-9390-2. PubMed PMID: 29417475. 4: Ogaki MB, Rocha KR, Terra MR, Furlaneto MC, Maia LF. Screening of the Enterocin-Encoding Genes and Antimicrobial Activity in Enterococcus Species. J Microbiol Biotechnol. 2016 Jun 28;26(6):1026-34. doi: 10.4014/jmb.1509.09020. PubMed PMID: 26907753. 5: Himeno K, Rosengren KJ, Inoue T, Perez RH, Colgrave ML, Lee HS, Chan LY, Henriques ST, Fujita K, Ishibashi N, Zendo T, Wilaipun P, Nakayama J, Leelawatcharamas V, Jikuya H, Craik DJ, Sonomoto K. Identification, Characterization, and Three-Dimensional Structure of the Novel Circular Bacteriocin, Enterocin NKR-5-3B, from Enterococcus faecium. Biochemistry. 2015 Aug 11;54(31):4863-76. doi: 10.1021/acs.biochem.5b00196. Epub 2015 Jul 31. PubMed PMID: 26174911. 6: Vandera E, Tsirka G, Kakouri A, Koukkou AI, Samelis J. Approaches for enhancing in situ detection of enterocin genes in thermized milk, and selective isolation of enterocin-producing Enterococcus faecium from Baird-Parker agar. Int J Food Microbiol. 2018 Sep 20;281:23-31. doi: 10.1016/j.ijfoodmicro.2018.05.020. Epub 2018 May 21. PubMed PMID: 29803907. 7: Norris GE, Patchett ML. The glycocins: in a class of their own. Curr Opin Struct Biol. 2016 Oct;40:112-119. doi: 10.1016/j.sbi.2016.09.003. Epub 2016 Sep 21. Review. PubMed PMID: 27662231. 8: Shehata AA, Tarabees R, Basiouni S, Gamil M, Kamal AS, Krüger M. Phenotypic and Genotypic Characterization of Bacteriocinogenic Enterococci Against Clostridium botulinum. Probiotics Antimicrob Proteins. 2017 Jun;9(2):182-188. doi: 10.1007/s12602-016-9240-z. PubMed PMID: 27914002. 9: Perez RH, Sugino H, Ishibashi N, Zendo T, Wilaipun P, Leelawatcharamas V, Nakayama J, Sonomoto K. Mutations near the cleavage site of enterocin NKR-5-3B prepeptide reveal new insights into its biosynthesis. Microbiology. 2017 Apr;163(4):431-441. doi: 10.1099/mic.0.000435. Epub 2017 Apr 12. PubMed PMID: 28113050. 10: Maky MA, Ishibashi N, Zendo T, Perez RH, Doud JR, Karmi M, Sonomoto K. Enterocin F4-9, a Novel O-Linked Glycosylated Bacteriocin. Appl Environ Microbiol. 2015 Jul;81(14):4819-26. doi: 10.1128/AEM.00940-15. Epub 2015 May 8. PubMed PMID: 25956765; PubMed Central PMCID: PMC4551185. 11: Al-Seraih A, Belguesmia Y, Baah J, Szunerits S, Boukherroub R, Drider D. Enterocin B3A-B3B produced by LAB collected from infant faeces: potential utilization in the food industry for Listeria monocytogenes biofilm management. Antonie Van Leeuwenhoek. 2017 Feb;110(2):205-219. doi: 10.1007/s10482-016-0791-5. Epub 2016 Nov 22. PubMed PMID: 27878401. 12: Caly DL, Chevalier M, Flahaut C, Cudennec B, Al Atya AK, Chataigné G, D'Inca R, Auclair E, Drider D. The safe enterocin DD14 is a leaderless two-peptide bacteriocin with anti-Clostridium perfringens activity. Int J Antimicrob Agents. 2017 Mar;49(3):282-289. doi: 10.1016/j.ijantimicag.2016.11.016. Epub 2017 Jan 16. PubMed PMID: 28104423. 13: Liu G, Wang Y, Li X, Hao X, Xu D, Zhou Y, Mehmood A, Wang C. Genetic and Biochemical Evidence That Enterococcus faecalis Gr17 Produces a Novel and Sec-Dependent Bacteriocin, Enterocin Gr17. Front Microbiol. 2019 Aug 13;10:1806. doi: 10.3389/fmicb.2019.01806. eCollection 2019. PubMed PMID: 31456764; PubMed Central PMCID: PMC6700250. 14: Teufel R. Preparation and Characterization of the Favorskiiase Flavoprotein EncM and Its Distinctive Flavin-N5-Oxide Cofactor. Methods Enzymol. 2018;604:523-540. doi: 10.1016/bs.mie.2018.01.036. Epub 2018 Mar 16. PubMed PMID: 29779666. 15: Grande Burgos MJ, Pulido RP, Del Carmen López Aguayo M, Gálvez A, Lucas R. The Cyclic Antibacterial Peptide Enterocin AS-48: Isolation, Mode of Action, and Possible Food Applications. Int J Mol Sci. 2014 Dec 8;15(12):22706-22727. Review. PubMed PMID: 25493478; PubMed Central PMCID: PMC4284732. 16: Öncül N, Yıldırım Z. Inhibitory effect of bacteriocins against Escherichia coli O157:H7. Food Sci Technol Int. 2019 Sep;25(6):504-514. doi: 10.1177/1082013219840462. Epub 2019 Apr 4. PubMed PMID: 30947545. 17: Rizzo A, Trauner D. Toward (-)-Enterocin: An Improved Cuprate Barbier Protocol To Overcome Strain and Sterical Hindrance. Org Lett. 2018 Apr 6;20(7):1841-1844. doi: 10.1021/acs.orglett.8b00353. Epub 2018 Mar 19. PubMed PMID: 29553746. 18: Tiwari SK, Sutyak Noll K, Cavera VL, Chikindas ML. Improved antimicrobial activities of synthetic-hybrid bacteriocins designed from enterocin E50-52 and pediocin PA-1. Appl Environ Microbiol. 2015 Mar;81(5):1661-7. doi: 10.1128/AEM.03477-14. Epub 2014 Dec 19. PubMed PMID: 25527560; PubMed Central PMCID: PMC4325174. 19: Wang Y, Li A, Jiang X, Zhang H, Mehmood K, Zhang L, Jiang J, Waqas M, Iqbal M, Li J. Probiotic Potential of Leuconostoc pseudomesenteroides and Lactobacillus Strains Isolated From Yaks. Front Microbiol. 2018 Dec 4;9:2987. doi: 10.3389/fmicb.2018.02987. eCollection 2018. PubMed PMID: 30564222; PubMed Central PMCID: PMC6289064. 20: Choyam S, Srivastava AK, Shin JH, Kammara R. Ocins for Food Safety. Front Microbiol. 2019 Aug 2;10:1736. doi: 10.3389/fmicb.2019.01736. eCollection 2019. Review. PubMed PMID: 31428063; PubMed Central PMCID: PMC6687839.

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Protosappanin A

Protosappanin A