Kurasoin B
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| Category | Enzyme inhibitors |
| Catalog number | BBF-01556 |
| CAS | |
| Molecular Weight | 279.33 |
| Molecular Formula | C18H17NO2 |
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Description
It is produced by the strain of Paecilomyces sp. FO-3184, Kurasoin B has the effect of inhibiting the protein fannicyl transferase.
Specification
| Synonyms | (+)-Kurasoin B |
| IUPAC Name | (3S)-3-hydroxy-4-(1H-indol-3-yl)-1-phenylbutan-2-one |
| Canonical SMILES | C1=CC=C(C=C1)CC(=O)C(CC2=CNC3=CC=CC=C32)O |
| InChI | InChI=1S/C18H17NO2/c20-17(10-13-6-2-1-3-7-13)18(21)11-14-12-19-16-9-5-4-8-15(14)16/h1-9,12,18-19,21H,10-11H2/t18-/m0/s1 |
| InChI Key | OLNJBNLERUYZTA-SFHVURJKSA-N |
Properties
| Appearance | White Powder |
Reference Reading
1. Total synthesis of the hydroxyketone kurasoin A using asymmetric phase-transfer alkylation
Merritt B Andrus, Erik J Hicken, Jeffrey C Stephens, D Karl Bedke J Org Chem. 2006 Oct 27;71(22):8651-4. doi: 10.1021/jo061395t.
The total synthesis of the farnesyltransferase inhibitor kurasoin A has been achieved using a novel asymmetric phase-transfer-catalyzed glycolate alkylation reaction. 2,5-Dimethoxyacetophenone 7 with cinchonidinium catalyst 9(10 mol %) and hydroxide base with pivaloyl benzyl bromide 8 provided S-alkylation product 10 in high yield (80-99%) and excellent enantioselectivity. Baeyer-Villiger oxidation, Weinreb amide formation, and benzyl Grignard addition to the TES-ether 17 gave the protected target. Lithium hydroxide and peroxide generated kurasoin A ([alpha](D) +8.4 degrees ) without isomerization.
2. Kurasoins A and B, new protein farnesyltransferase inhibitors produced by Paecilomyces sp. FO-3684. II. Structure elucidation and total synthesis
R Uchida, K Shiomi, T Sunazuka, J Inokoshi, A Nishizawa, T Hirose, H Tanaka, Y Iwai, S Omura J Antibiot (Tokyo). 1996 Sep;49(9):886-9. doi: 10.7164/antibiotics.49.886.
The structures of new protein farnesyltransferase inhibitors, kurasoins A and B, were elucidated by NMR study. Kurasoins A and B are acyloin compounds having in common a 3-hydroxy-1-phenyl-2-butanone moiety, to which p-hydroxyphenyl and 3-indolyl moieties respectively, are connected at C-4. The structures were confirmed by total synthesis.
3. Neuroactive diol and acyloin metabolites from cone snail-associated bacteria
Zhenjian Lin, Lenny Marett, Ronald W Hughen, Malem Flores, Imelda Forteza, Mary Anne Ammon, Gisela P Concepcion, Samuel Espino, Baldomero M Olivera, Gary Rosenberg, Margo G Haygood, Alan R Light, Eric W Schmidt Bioorg Med Chem Lett. 2013 Sep 1;23(17):4867-9. doi: 10.1016/j.bmcl.2013.06.088. Epub 2013 Jul 8.
The bacterium Gordonia sp. 647W.R.1a.05 was cultivated from the venom duct of the cone snail, Conus circumcisus. The Gordonia sp. organic extract modulated the action potential of mouse dorsal root ganglion neurons. Assay-guided fractionation led to the identification of the new compound circumcin A (1) and 11 known analogs (2-12). Two of these compounds, kurasoin B (7) and soraphinol A (8), were active in a human norepinephrine transporter assay with Ki values of 2575 and 867 nM, respectively. No neuroactivity had previously been reported for compounds in this structural class. Gordonia species have been reproducibly isolated from four different cone snail species, indicating a consistent association between these organisms.
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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 ╳
