- Solution-phase and solid-phase syntheses of enzyme inhibitor RK-682 and antibiotic agglomerins
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The enzyme inhibitor RK-682 (5A)-(+)-1 was prepared in solution and on a solid support from (2R)-glycerates in five steps and ca. 40% overall yield. Key steps were a ring-closing tandem addition-Wittig alkenation reaction of the respective protected or im
- Schobert, Rainer,Jagusch, Garsten
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p. 6129 - 6132
(2007/10/03)
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- 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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RK-682 was reported to be a potent protein tyrosine phosphatase inhibitor. We found that (R)-3-hexadecanoyl-5-hydroxymethyltetronic acid (I) 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)-I 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,Sampe,Kojima,Baba,Morisaki,Hashimoto
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p. 206 - 212
(2007/10/03)
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- Asymmetric synthesis of RK-682 and its analogs, and evaluation of their protein phosphatase inhibitory activities
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We report an asymmetric synthesis of a potent tyrosine phosphatase inhibitor, RK-682 and its analogs. The absolute stereochemistry of RK-682 was determined to be (R). The inhibitory activities of RK-682 and its analogs, (R)-1a, (S)-1a, (R)-1b and (R)-1c toward various protein phosphatases (VHR, cdc25A, cdc25B, and PPI) are also reported.
- Sodeoka, Mikiko,Sampe, Ruriko,Kagamizono, Terumi,Osada, Hiroyuki
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p. 8775 - 8778
(2007/10/03)
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