RK-682 hemicalcium
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04285 |
| CAS | 332131-32-5 |
| Molecular Weight | 419.8 |
| Molecular Formula | C18H14ClF4NO4 |
| Purity | >95% by HPLC |
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Description
It is a dimeric calcium complex of the major analogue of tetronic acid complex isolated from streptomyces. It inhibits protein tyrosine phosphatases, phospoholipase A2, heparinase and HIV-1 protease.
Specification
| Related CAS | 150627-37-5 (free acid) |
| Synonyms | 332131-32-5;TAN 1364B, CI 010;calcium;(2R)-4-hexadecanoyl-2-(hydroxymethyl)-5-oxo-2H-furan-3-olate;RK-682 (calcium salt);Calcium (R)-2-(hydroxymethyl)-5-oxo-4-palmitoyl-2,5-dihydrofuran-3-olate; |
| Storage | Please store the product under the recommended conditions in the Certificate of Analysis. |
| IUPAC Name | calcium;(2R)-4-hexadecanoyl-2-(hydroxymethyl)-5-oxo-2H-furan-3-olate |
| Canonical SMILES | CC(C)C(=O)OC1=CC(=C(C=C1C(=O)NC2=CC=C(C=C2)OC(F)(F)F)Cl)F |
| InChI | InChI=1S/2C21H36O5.Ca/c2*1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-17(23)19-20(24)18(16-22)26-21(19)25;/h2*18,22,24H,2-16H2,1H3;/q;;+2/p-2/t2*18-;/m11./s1 |
| InChI Key | LNDPLBYJXMIJFP-ZMFXSWHNSA-L |
| Source | Streptomyces sp. |
Properties
| Appearance | White Solid |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1. Asymmetric synthesis of a 3-acyltetronic acid derivative, RK-682, and formation of its calcium salt during silica gel column chromatography
S Kojima, R Sampe, N Morisaki, Y Baba, Y Hashimoto, M Sodeoka Chem Pharm Bull (Tokyo) . 2001 Feb;49(2):206-12. doi: 10.1248/cpb.49.206.
RK-682 was reported to be a potent protein tyrosine phosphatase inhibitor. We found that (R)-3-hexadecanoyl-5-hydroxymethyltetronic acid (1) was easily converted to its calcium salt during column chromatography on Silica gel 60, and this calcium salt was identical to RK-682 originally isolated from a natural source. Here we report details of the asymmetric synthesis of (R)-1 and its conversion to the calcium salt. Fast atom bombardment mass spectrometric (FAB-MS) analysis of the free and calcium salt forms of RK-682 is also reported.
2. Conversion of Ca2+ salt of an organic compound to its Li+ salt to simplify the fast atom bombardment mass spectrum
Hisayoshi Kobayashi, Yoshiyasu Baba, Yuichi Hashimoto, Naoko Morisaki, Mikiko Sodeoka, Kazuo Nagasawa Chem Pharm Bull (Tokyo) . 2003 Nov;51(11):1341-4. doi: 10.1248/cpb.51.1341.
The FAB mass spectrum of the Ca(2+) salt of RK-682 (1, MW 368), a potent protein tyrosine phosphatase inhibitor, shows a complex pattern due to Ca(2+) adduct ions with multimers of 1 and their decomposition ions. Addition of LiCl greatly simplified the FAB mass spectrum, providing a prominent Li(+) adduct ion of 1 at m/z 381 [M+2Li-H](+). The addition of LiCl also greatly simplified the FAB mass spectrum of calcium pantothenate. This approach may be generally useful for molecular weight determination of multivalent metal salts of organic compounds, or organic compounds that can form Li salts, by FAB mass spectrometry.
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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 ╳
