Ebelactone A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01776 |
| CAS | 76808-16-7 |
| Molecular Weight | 338.48 |
| Molecular Formula | C20H34O4 |
| Purity | ≥98% |
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Description
It is produced by the strain of Streptomyces aburaviensis. It has the inhibitory effect on Esterases (IC50 is 0.56 μg/mL), Pancreatic lipase (IC50 is 0.003 μg/mL) and Cutinase on fungal cells.
Specification
| Synonyms | 2-Oxetanone, 4-(8-hydroxy-1,3,5,7,9-pentamethyl-6-oxo-3-undecenyl)-3-methyl-, (3S-(3-alpha,4-beta(1R*,3E,5S*,7R*,8S*,9S*)))-; (-)-ebelactone a |
| Storage | 2-8 °C |
| IUPAC Name | (3S,4S)-4-[(E,2S,6R,8S,9R,10R)-9-hydroxy-4,6,8,10-tetramethyl-7-oxododec-4-en-2-yl]-3-methyloxetan-2-one |
| Canonical SMILES | CCC(C)C(C(C)C(=O)C(C)C=C(C)CC(C)C1C(C(=O)O1)C)O |
| InChI | InChI=1S/C20H34O4/c1-8-12(3)17(21)15(6)18(22)13(4)9-11(2)10-14(5)19-16(7)20(23)24-19/h9,12-17,19,21H,8,10H2,1-7H3/b11-9+ |
| InChI Key | WOISDAHQBUYEAF-QIQXJRRPSA-N |
Properties
| Appearance | Colorless Powder |
| Antibiotic Activity Spectrum | Fungi |
| Boiling Point | 462.8 °C at 760 mmHg |
| Melting Point | 86 °C |
| Density | 1.011 g/cm3 |
| Solubility | Soluble in Ethanol |
Reference Reading
1. Purification and characterization of a rat liver enzyme that hydrolyzes valaciclovir, the L-valyl ester prodrug of acyclovir
J E Reardon, B M Merrill, P de Miranda, T C Burnette, J A Harrington J Biol Chem . 1995 Jun 30;270(26):15827-31. doi: 10.1074/jbc.270.26.15827.
Valaciclovir is an oral prodrug of the antiherpetic agent acyclovir. An enzyme that hydrolyzes valaciclovir to acyclovir, valaciclovir hydrolase (VACVase), was purified from rat liver and characterized. VACVase was a basic (pI 9.4) protein associated with mitochondria. It was monomeric and had a molecular mass of 29 kDa. Amino acid sequences of six VACVase peptides, including its NH2 terminus (13 amino acids) and accounting for approximately 20% of its complete sequence, were not found in the SwissProt protein data base. VACVase hydrolyzed other amino acid esters of acyclovir in addition to valaciclovir (kcat/Km = 58 mM-1 s-1), with a preference for the L-alanyl (kcat/Km = 226 mM-1 s-1) and L-methionyl (kcat/Km = 200 mM-1 s-1) esters. It did not hydrolyze other types of esters or numerous di- and tripeptides and aminoacyl-beta-naphthylamides. Hydrolysis of valaciclovir by VACVase was not inhibited by amastatin, antipain, aprotinin, bestatin, chymostatin, E-64, EDTA, ebelactone A, ebelactone B, elastatinal, leupeptin, pepstatin, or phosphoramidon. It was neither inhibited nor activated by Ca2+, Co2+, Mg2+, Mn2+, or Zn2+. Therefore, this enzyme is not a typical esterase or peptidase and, to our knowledge, it has not been described previously. Its physiological function is not known; however, it may play a significant role in the biotransformation of valaciclovir to acyclovir.
2. Stereocontrolled total synthesis of (-)-ebelactone A
Amit K Mandal Org Lett . 2002 Jun 13;4(12):2043-5. doi: 10.1021/ol020058d.
[structure: see text] The highly stereocontrolled hydroboration of an alkene, a subsequent Suzuki-Miyaura cross-coupling reaction, a silylcupration on a nonterminal acetylene, and an iododesilylation were the key steps in a convergent total synthesis of (-)-ebelactone A.
3. β-Lactone natural products and derivatives inactivate homoserine transacetylase, a target for antimicrobial agents
Ishac Nazi, Paul H M Harrison, Gerard D Wright, Gianfranco De Pascale J Antibiot (Tokyo) . 2011 Jul;64(7):483-7. doi: 10.1038/ja.2011.37.
Homoserine transacetylase (HTA) catalyzes the transfer of an acetyl group from acetyl-CoA to the hydroxyl group of homoserine. This is the first committed step in the biosynthesis of methionine (Met) from aspartic acid in many fungi, Gram-positive and some Gram-negative bacteria. The enzyme is absent in higher eukaryotes and is important for microorganism growth in Met-poor environments, such as blood serum, making HTA an attractive target for new antimicrobial agents. HTA catalyzes acetyl transfer via a double displacement mechanism facilitated by a classic Ser-His-Asp catalytic triad located at the bottom of a narrow actives site tunnel. We explored the inhibitory activity of several β-lactones to block the activity of HTA. In particular, the natural product ebelactone A, a β-lactone with a hydrophobic tail was found to be a potent inactivator of HTA from Haemophilus influenzae. Synthetic analogs of ebelactone A demonstrated improved inactivation characteristics. Covalent modification of HTA was confirmed by mass spectrometry, and peptide mapping identified Ser143 as the modified residue, consistent with the known structure and mechanism of the enzyme. These results demonstrate that β-lactone inhibitors are excellent biochemical probes of HTA and potential leads for new antimicrobial agents.
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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 ╳
