4-hexadecanoyl-3-hydroxy-2-(hydroxymethyl)-2H-furan-5-one

BeschreibungTAN 1364B is a protein tyrosine phosphatase (PTP) inhibitor and the racemic and monomeric form of RK-682 . TAN 1364B inhibits the activity of the PTPs LMW-PTP, CDC25B, and PTP1B (IC50s = 8.6, 12.4, and 0.7 μM, respectively), but the inhibitory activity against LMW-PTP and CDC25B is blocked in the presence of magnesium. TAN 1364B forms aggregates in solution and binds to both the PTP binding site and to protein surfaces.

VerwendenTAN 1364B (RK-682) is the most abundant analogue of a tetronic acid complex isolated from Streptomyces species, first patented by Takeda in 1993 and more formally identified by Ciba Geigy as the sodium salt of 3-hexadecanoyl-5-hydroxymethyltetronic acid. In 1995 researchers at RIKEN reported the isolation of 3-hexadecanoyl-5-hydroxymethyltetronic acid, named as RK-682. Subsequent synthesis in 2001 showed that the RIKEN RK-682 was in fact the calcium complex of TAN 1364B formed as an artefact during silica chromatography. As the complex, salt or free acid, TAN 1364B inhibits protein tyrosine phosphatases, phospoholipase A2, heparinase and HIV-1 protease. However, it is unclear whether biological activity is due to the monomer (TAN 1364B) or dimeric complex (RK-682)