Amidepsine B
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| Category | Enzyme inhibitors |
| Catalog number | BBF-00439 |
| CAS | 169181-29-7 |
| Molecular Weight | 553.51 |
| Molecular Formula | C28H27NO11 |
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Description
It is produced by the strain of Humicola sp. FO-2942. It inhibits DGAT activity, and the IC50 of rat liver microsomes DGAT is 19.2 X 10-6mol/L. It also inhibits triacylglycerol formation in intact Raji cells.
Specification
| IUPAC Name | 2-[[2-hydroxy-4-[2-hydroxy-4-(2-hydroxy-4-methoxy-6-methylbenzoyl)oxy-6-methylbenzoyl]oxy-6-methylbenzoyl]amino]propanoic acid |
| Canonical SMILES | CC1=CC(=CC(=C1C(=O)OC2=CC(=C(C(=C2)C)C(=O)OC3=CC(=C(C(=C3)C)C(=O)NC(C)C(=O)O)O)O)O)OC |
| InChI | InChI=1S/C28H27NO11/c1-12-7-17(10-19(30)22(12)25(33)29-15(4)26(34)35)39-28(37)24-14(3)8-18(11-21(24)32)40-27(36)23-13(2)6-16(38-5)9-20(23)31/h6-11,15,30-32H,1-5H3,(H,29,33)(H,34,35) |
| InChI Key | MRXFLJQBLAIVOO-UHFFFAOYSA-N |
Reference Reading
1. Amidepsines, inhibitors of diacylglycerol acyltransferase produced by Humicola sp. FO-2942. II. Structure elucidation of amidepsines A, B and C
H Tomoda, N Tabata, M Ito, S Omura J Antibiot (Tokyo). 1995 Sep;48(9):942-7. doi: 10.7164/antibiotics.48.942.
Structures of amidepsines A, B, C and D, diacylglycerol acyltransferase (DGAT) inhibitors, were determined by spectroscopic studies including various NMR measurements. They were elucidated as 2-hydroxy-4-[[2-hydroxy-4-[(2,4-dimethoxy-6-methylbenzoyl) oxy]6-methylbenzoyl]-oxy]-6-methylbenzoic acid N-alanine amide for amidepsine A, 2-hydroxy-4-[[2-hydroxy-4-[(2-hydroxy-4-methoxy-6-methylbenzoyl) oxy]6-methylbenzoyl]oxy]-6-methylbenzoic acid N-alanine amide for amidepsine B and 2-hydroxy-4-[[2-hydroxy-4-[(2-hydroxy-4-methoxy-6-methylbenzoyl) oxy]6-methylbenzoyl]oxy]-6-methylbenzoic acid N-valine amide for amidepsine C. Amidepsine D was identified with 2,4-di-O-methylgryphoric acid.
2. Amidepsines, inhibitors of diacylglycerol acyltransferase produced by Humicola sp. FO-2942. I. Production, isolation and biological properties
H Tomoda, M Ito, N Tabata, R Masuma, Y Yamaguchi, S Omura J Antibiot (Tokyo). 1995 Sep;48(9):937-41. doi: 10.7164/antibiotics.48.937.
Humicola sp. FO-2942, a soil isolate, was found to produce a series of new inhibitors of diacylglycerol acyltransferase (DGAT). Three active compounds, designated amidepsines A, B and C, were isolated from the fermentation broth of the producing strain by solvent extraction, silica gel column chromatography, ODS column chromatography and HPLC. Amidepsines inhibit DGAT activity with IC50 values of 10.2 approximately 51.6 microM in an enzyme assay system using rat liver microsomes. Amidepsines also showed specific inhibition of triacylglycerol formation in intact Raji cells, indicating that they inhibit DGAT activity in living cells.
3. Total synthesis of amidepsine B and revision of its absolute configuration
Tohru Nagamitsu, Kaori Marumoto, Asami Nagayasu, Takeo Fukuda, Shiho Arima, Ryuji Uchida, Taichi Ohshiro, Yoshihiro Harigaya, Hiroshi Tomoda, Satoshi Omura J Antibiot (Tokyo). 2009 Feb;62(2):69-74. doi: 10.1038/ja.2008.12. Epub 2009 Jan 23.
The total synthesis of (-)-amidepsine B, a potent diacylglycerol acyltransferase inhibitor, has been achieved. This synthetic study resulted in the revision of the previously assigned stereostructure of the natural amidepsine B and determined the absolute configuration.
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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 ╳
