Asymmetric synthesis of a 3-acyltetronic acid derivative, RK-682, and formation of its calcium salt during silica gel column chromatography.
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.
Sodeoka
M
M
Institute for Chemical Reaction Science, Tohoku University, Sendai, Miyagi, Japan. sodeoka@icrs.tohoku.ac.jp
Sampe
R
R
Kojima
S
S
Baba
Y
Y
Morisaki
N
N
Hashimoto
Y
Y
D002118:Calcium / Q000737:chemistry*; D002850:Chromatography, Gel / Q000379:methods*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010749:Phosphoprotein Phosphatases / Q000037:antagonists & inhibitors* / Q000138:chemical synthesis* / Q000737:chemistry; D016339:Spectrometry, Mass, Fast Atom Bombardment
D004791:Enzyme Inhibitors; C094097:RK 682; D010749:Phosphoprotein Phosphatases; D002118:Calcium