Cyclooctatin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01113 |
| CAS | 139552-97-9 |
| Molecular Weight | 322.49 |
| Molecular Formula | C20H34O3 |
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Description
It is produced by the strain of Sreptomyces melanosporofaciens M1614-43F2. It can inhibit the hemolysis phospholipase [EC 3.1.1.5] (Lyso-PL) activity. Terpentecin as substrates, it inhibits Lyso-PL, PL-A2, PL-C and PL-D with IC50 of 2.9 μg/mL, 65.0 μg/mL, 70.0 μg/mL and >100 μg/mL, respectively. Ki is 4.8 X 10-6 mol/L.
Specification
| Synonyms | Dicyclopenta(a,d)cyclooctene-3,4-diol,1,2,3,3a,4,5,7,8,9,9a,10,10a-dodecahydro-4,9a-dimethyl-1-(hydroxymethyl)-7-(1-methylethyl)-; 1-(Hydroxymethyl)-7-isopropyl-4,9a-dimethyl-1,2,3,3a,4,5,7,8,9,9a,10,10a-dodecahydrodicyclopenta[a,d]cyclooctene-3,4-diol |
| IUPAC Name | (10Z)-4-(hydroxymethyl)-1,8-dimethyl-12-propan-2-yltricyclo[9.3.0.03,7]tetradec-10-ene-6,8-diol |
| Canonical SMILES | CC(C)C1CCC2(C1=CCC(C3C(CC(C3C2)CO)O)(C)O)C |
| InChI | InChI=1S/C20H34O3/c1-12(2)14-5-7-19(3)10-15-13(11-21)9-17(22)18(15)20(4,23)8-6-16(14)19/h6,12-15,17-18,21-23H,5,7-11H2,1-4H3/b16-6- |
| InChI Key | MSKFOQCDNOFJAT-SOFYXZRVSA-N |
Properties
| Appearance | Colorless Powder |
| Boiling Point | 465.2 °C at 760 mmHg |
| Melting Point | 183-185 °C (dec.) |
| Density | 1.10 g/cm3 |
| Solubility | Soluble in Methanol, Acetone, DMSO; Insoluble in Water |
Reference Reading
1. The energetic viability of an unexpected skeletal rearrangement in cyclooctatin biosynthesis
Young J Hong, Dean J Tantillo Org Biomol Chem. 2015 Nov 7;13(41):10273-8. doi: 10.1039/c5ob01785h.
Results of density functional theory calculations on possible mechanisms for formation of the diterpenoid cyclooctatin are described. These results are consistent with the involvement of an unexpected 1,3-alkyl shift that interconverts two cyclopropylcarbinyl carbocations and interchanges the positions of two carbon atoms in an 8-membered ring. Predictions for future experiments to provide further support of this mechanism also are described.
2. Understanding the role of active site residues in CotB2 catalysis using a cluster model
Keren Raz, Ronja Driller, Thomas Brück, Bernhard Loll, Dan T Major Beilstein J Org Chem. 2020 Jan 8;16:50-59. doi: 10.3762/bjoc.16.7. eCollection 2020.
Terpene cyclases are responsible for the initial cyclization cascade in the multistep synthesis of a large number of terpenes. CotB2 is a diterpene cyclase from Streptomyces melanosporofaciens, which catalyzes the formation of cycloocta-9-en-7-ol, a precursor to the next-generation anti-inflammatory drug cyclooctatin. In this work, we present evidence for the significant role of the active site's residues in CotB2 on the reaction energetics using quantum mechanical calculations in an active site cluster model. The results revealed the significant effect of the active site residues on the relative electronic energy of the intermediates and transition state structures with respect to gas phase data. A detailed understanding of the role of the enzyme environment on the CotB2 reaction cascade can provide important information towards a biosynthetic strategy for cyclooctatin and the biomanufacturing of related terpene structures.
3. Investigation on antimicrobial agents of the terrestrial Streptomyces sp. BCC71188
Khomsan Supong, Paranee Sripreechasak, Somboon Tanasupawat, Kannawat Danwisetkanjana, Pranee Rachtawee, Pattama Pittayakhajonwut Appl Microbiol Biotechnol. 2017 Jan;101(2):533-543. doi: 10.1007/s00253-016-7804-1. Epub 2016 Aug 23.
The terrestrial actinomycete strain BCC71188 was identified as Streptomyces by its morphology (having spiral chain spore on the aerial mycelium), chemotaxonomy (containing LL-diaminopimelic acid in the cell wall), and 16S rRNA gene sequence analysis [showing high similarity values compared with Streptomyces samsunensis M1463T (99.85 %) and Streptomyces malaysiensis NBRC 16446T (99.40 %)]. The crude extract exhibited antimalarial against Plasmodium falciparum (IC50 0.19 μg/ml), anti-TB against Mycobacterial tuberculosis (MIC 6.25 μg/ml), and antibacterial against Bacillus cereus (MIC 1.56 μg/ml) activities. Therefore, chemical investigation was conducted by employing bioassay-guided method and led to the isolation of 19 compounds including two cyclic peptides (1-2), five macrolides (3-7), new naphthoquinone (8), nahuoic acid C (9), geldanamycin derivatives (10-13), cyclooctatin (14), germicidins A (15) and C (16), actinoramide A (17), abierixin, and 29-O-methylabierixin. These isolated compounds were evaluated for antimicrobial activity, such as antimalarial, anti-TB, and antibacterial activities, and for cytotoxicity against both cancerous (MCF-7, KB, NCI-H187) and non-cancerous (Vero) cells. Compounds 1-7, 10-14 exhibited antimalarial (IC50 0.22-7.14 μg/ml), and elaiophylin analogs (4-6) displayed anti-TB (MIC 0.78-12.00 μg/ml) and B. cereus (MIC 0.78-3.13 μg/ml) activities. Compounds 1, 2, 14, and abierixin displayed weak cytotoxicity, indicating a potential for 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 ╳
