Enacyloxin IIa
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| Category | Antibiotics |
| Catalog number | BBF-01222 |
| CAS | 126518-41-0 |
| Molecular Weight | 702.62 |
| Molecular Formula | C33H45Cl2NO11 |
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Description
It is produced by the strain of Frateuria sp. W-315. It is a polyene antibiotic, which has the activity of anti-gram-positive bacteria and negative bacteria. the activity of anti-fungus is weak, and has no effect on yeast.
Specification
| Synonyms | (1S,3R,4S)-3-{[(2E,4E,6E,8E,10Z,12S,13R,14S,17R,18S,19R,20E)-19-(carbamoyloxy)-11,18-dichloro-13,14,17-trihydroxy-6,12-dimethyl-15-oxotricosa-2,4,6,8,10,20-hexaenoyl]oxy}-4-hydroxycyclohexanecarboxylic acid; Enacyloxin II; Enacyloxin iia; Enx iia |
| IUPAC Name | (1S,3R,4S)-3-[(2E,4E,6E,8E,10Z,12S,13R,14S,17R,18S,19R,20E)-19-carbamoyloxy-11,18-dichloro-13,14,17-trihydroxy-6,12-dimethyl-15-oxotricosa-2,4,6,8,10,20-hexaenoyl]oxy-4-hydroxycyclohexane-1-carboxylic acid |
| Canonical SMILES | CCC=CC(C(C(CC(=O)C(C(C(C)C(=CC=CC=C(C)C=CC=CC(=O)OC1CC(CCC1O)C(=O)O)Cl)O)O)O)Cl)OC(=O)N |
| InChI | InChI=1S/C33H45Cl2NO11/c1-4-5-13-26(47-33(36)45)29(35)24(38)18-25(39)31(42)30(41)20(3)22(34)12-8-6-10-19(2)11-7-9-14-28(40)46-27-17-21(32(43)44)15-16-23(27)37/h5-14,20-21,23-24,26-27,29-31,37-38,41-42H,4,15-18H2,1-3H3,(H2,36,45)(H,43,44)/b8-6+,11-7+,13-5+,14-9+,19-10+,22-12-/t20-,21+,23+,24-,26-,27-,29+,30-,31-/m1/s1 |
| InChI Key | IWBADCVFZDCUTN-OCXJTLLTSA-N |
Properties
| Appearance | Yellow Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; Fungi |
| Boiling Point | 938.3 °C at 760 mmHg |
| Density | 1.33 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Antimicrobial activity of enacyloxin IIa and gladiolin against the urogenital pathogens Neisseria gonorrhoeae and Ureaplasma spp
N L Heath, R S Rowlands, G Webster, E Mahenthiralingam, M L Beeton J Appl Microbiol. 2021 May;130(5):1546-1551. doi: 10.1111/jam.14858. Epub 2020 Oct 21.
Aims: To determine the antimicrobial activity of enacyloxin IIa and gladiolin against Neisseria gonorrhoeae and Ureaplasma spp. Methods and results: The Burkholderia polyketide antibiotics enacyloxin IIa and gladiolin were tested against 14 N. gonorrhoeae and 10 Ureaplasma spp. isolates including multidrug-resistant N. gonorrhoeae isolates WHO V, WHO X and WHO Z as well as macrolide, tetracycline and ciprofloxacin-resistant ureaplasmas. Susceptibility testing of N. gonorrhoeae was carried out by agar dilution, whereas broth micro-dilution and growth kinetic assays were used for Ureaplasma spp. The MIC range for enacyloxin IIa and gladiolin against N. gonorrhoeae was 0·015-0·06 mg l-1 and 1-2 mg l-1 respectively. The presence of resistance to front line antibiotics had no effect on MIC values. The MIC range for enacyloxin IIa against Ureaplasma spp. was 4-32 mg l-1 with a clear dose-dependent effect when observed using a growth kinetic assay. Gladiolin had no antimicrobial activity on Ureaplasma spp. at 32 mg l-1 and limited impact on growth kinetics. Conclusions: Enacyloxin IIa and gladiolin antibiotics have antimicrobial activity against a range of antibiotic susceptible and resistant N. gonorrhoeae and Ureaplasma isolates. Significance and impact of the study: This study highlights the potential for a new class of antimicrobial against pathogens in which limited antibiotics are available. Development of these compounds warrants further investigation in the face of emerging extensively drug-resistant strains.
2. Towards improved understanding of intersubunit interactions in modular polyketide biosynthesis: Docking in the enacyloxin IIa polyketide synthase
Fanny Risser, Sabrina Collin, Raphael Dos Santos-Morais, Arnaud Gruez, Benjamin Chagot, Kira J Weissman J Struct Biol. 2020 Oct 1;212(1):107581. doi: 10.1016/j.jsb.2020.107581. Epub 2020 Jul 25.
Modular polyketide synthases (PKSs) are molecular-scale assembly lines comprising multiple gigantic polypeptide subunits. Faithful ordering of the subunits is mediated by extreme C- and N-terminal regions called docking domains (DDs). Decrypting how specificity is achieved by these elements is important both for understanding PKS function and modifying it to generate useful polyketide analogues for biological evaluation. Here we report the biophysical and structural characterisation of all six PKS/PKS interfaces in the unusual, chimaeric cis-AT/trans-AT PKS pathway responsible for biosynthesis of the antibiotic enacyloxin IIa in Burkholderia ambifaria. Taken together with previous work, our data reveal that specificity is achieved in the enacyloxin PKS by deploying at least three functionally orthogonal classes of DDs. We also demonstrate for the first time that cis-AT PKS subunits incorporate DDs with intrinsically disordered character, reinforcing the utility of such regions for achieving both medium affinity and high specificity at PKS intersubunit junctions. Overall, this work substantially increases the number of orthogonal DDs available for creating novel, highly-specific interfaces within cis- and trans-AT PKSs and their hybrids. It also reveals unexpected sequence/structure relationships in PKS DDs, identifying major current limitations to both accurately predicting and categorising these useful protein-protein interaction motifs.
3. Elfamycins: inhibitors of elongation factor-Tu
Samantha M Prezioso, Nicole E Brown, Joanna B Goldberg Mol Microbiol. 2017 Oct;106(1):22-34. doi: 10.1111/mmi.13750. Epub 2017 Aug 9.
Elfamycins are a relatively understudied group of antibiotics that target the essential process of translation through impairment of EF-Tu function. For the most part, the utility of these compounds has been as laboratory tools for the study of EF-Tu and the ribosome, as their poor pharmacokinetic profile and solubility has prevented implementation as therapeutic agents. However, due to the slowing of the antibiotic pipeline and the rapid emergence of resistance to approved antibiotics, this group is being reconsidered. Some researchers are using screens for novel naturally produced variants, while others are making directed, systematic chemical improvements on publically disclosed compounds. As an example of the latter approach, a GE2270 A derivative, LFF571, has completed phase 2 clinical trials, thus demonstrating the potential for elfamycins to become more prominent antibiotics in the future.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
