Versatile synthesis of phenoxydiazirine-based fatty acid analogues and photoreactive galactosylceramide.
Makoto Hashimoto, Yasumaru Hatanaka, Kensuke Nabeta
Index: Bioorg. Med. Chem. Lett. 12(1) , 89-91, (2002)
Full Text: HTML
Abstract
A versatile synthesis of diazirine-based photoreactive fatty acid analogues is reported. The key step is phenoxy alkylation of diazirine with halo alkyl acid esters. The conditions described will be acceptable for the synthesis of various alkyl-length derivatives. The fatty acid derivatives are acceptors for reverse reactions of sphingolipid ceramide N-deacylase (SCDase), which catalyzes the condensation of psychosine and fatty acids to form photoreactive galactosylceramide. The photoreactive galactosylceramide can also be prepared with chemical synthesis, condensation of psychosine and fatty acid succinimidyl ester, and is recognized with anti-GarCer antibody both before and after irradiation.
Related Compounds
Related Articles:
Studies on ω-Oxidation of Fatty Acids in vitro. KAMEI S, et al.
[J. Biochem. 56(1) , 72-76, (1964)]
A Three Step Synthesis of 11-Cycloheptylundecanoic Acid, a Component of the Thermoacidophile Alicyclobacillus cycloheptanicus. Hassarajani SA and Mamdapur VR.
[Molecules 3(2) , 41-43, (1998)]