Asymmetric synthesis of a 3-acyltetronic acid derivative, RK-682, and formation of its calcium salt during silica gel column chromatography

Asymmetric synthesis of a 3-acyltetronic acid derivative, RK-682, and formation of its calcium salt during silica gel column chromatography
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DOI:
10.1248/cpb.49.206
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发表时间:
2001-02-01
影响因子:
1.7
通讯作者:
Hashimoto, Y
Hashimoto, Y
中科院分区:
医学4区
文献类型:
--
作者:
Sodeoka, M;Sampe, R;Hashimoto, Y

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RK-682 was reported to be a potent protein tyrosine phosphatase inhibitor. We found that (R)-3-hexadecanoyl -5-hydrolxymethyltetronic 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.