Conocandin
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| Category | Antibiotics |
| Catalog number | BBF-01053 |
| CAS | 61371-61-7 |
| Molecular Weight | 294.43 |
| Molecular Formula | C18H30O3 |
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Description
It is produced by the strain of Hormococcus conorium. It has strong antifungal activity.
Specification
| Synonyms | 2-Methylidene-10-methyl-trans-3,4-epoxy-9-hexadecenoic acid |
| IUPAC Name | 2-[(2S,3S)-3-[(E)-6-methyldodec-5-enyl]oxiran-2-yl]prop-2-enoic acid |
| Canonical SMILES | CCCCCCC(=CCCCCC1C(O1)C(=C)C(=O)O)C |
| InChI | InChI=1S/C18H30O3/c1-4-5-6-8-11-14(2)12-9-7-10-13-16-17(21-16)15(3)18(19)20/h12,16-17H,3-11,13H2,1-2H3,(H,19,20)/b14-12+/t16-,17-/m0/s1 |
| InChI Key | WSCIWZRMZZZKRD-KIXISSKZSA-N |
Properties
| Appearance | Viscous Oily Matter |
| Antibiotic Activity Spectrum | Fungi |
Reference Reading
1. A stereodivergent synthesis of beta-hydroxy-alpha-methylene lactones via vinyl epoxides
Marion Davoust, Frédéric Cantagrel, Patrick Metzner, Jean-François Brière Org Biomol Chem. 2008 Jun 7;6(11):1981-93. doi: 10.1039/b802310g. Epub 2008 Apr 9.
A catalytic diastereoselective sulfonium ylide epoxidation of aldehydes furnished original vinyl epoxides, having an MBH backbone. These highly functionalized building blocks were used for a formal synthesis of the antibiotic conocandin, and opened up a stereodivergent route towards beta-hydroxy-alpha-methylene lactones, core units of naturally occurring compounds. Under acidic conditions, the oxiranes were mainly transformed, with moderate to good yields, into trans beta-hydroxy-alpha-methylene lactones. On the other hand, a user-friendly palladium-catalysed CO2 insertion and cyclisation sequence gave the cis beta-hydroxy-alpha-methylene lactone counterparts along with an interesting cis-trans equilibration of the pi-allyl intermediates.
2. Chemical Exchanges between Multilateral Symbionts
Munhyung Bae, Emily Mevers, Gleb Pishchany, Sarah G Whaley, Charles O Rock, David R Andes, Cameron R Currie, Monica T Pupo, Jon Clardy Org Lett. 2021 Mar 5;23(5):1648-1652. doi: 10.1021/acs.orglett.1c00068. Epub 2021 Feb 16.
Herein is a report on the molecular exchange occurring between multilateral symbiosis partners-a tit-for-tat exchange that led to the characterization of two new metabolites, conocandin B (fungal-derived) and dentigerumycin F (bacterial-derived). The structures were determined by NMR, mass spectrometry, genomic analysis, and chemical derivatizations. Conocandin B exhibits antimicrobial activity against both the bacterial symbionts of fungus-growing ant and human pathogenic strains by selectively inhibiting FabH, thus disrupting fatty acid biosynthesis.
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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 ╳
