Versatile synthesis of phenoxydiazirine-based fatty acid analogues and photoreactive galactosylceramide.
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.
Hashimoto
Makoto
M
Department of Bioresource Science, Obihiro University of Agriculture and Veterinary Medicine, Inada-cho, Obihiro 080-8555, Hokkaido, Japan. hasimoto@obihiro.ac.jp
Hatanaka
Yasumaru
Y
Nabeta
Kensuke
K
D000478:Alkylation; D000581:Amidohydrolases / Q000378:metabolism; D015153:Blotting, Western; D003978:Diazomethane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D005227:Fatty Acids / Q000138:chemical synthesis* / Q000737:chemistry; D005699:Galactosylceramides / Q000737:chemistry*; D010647:Phenyl Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D019920:Photoaffinity Labels / Q000138:chemical synthesis* / Q000737:chemistry; D010782:Photolysis; D011609:Psychosine / Q000737:chemistry / Q000378:metabolism; D013057:Spectrum Analysis; D013329:Structure-Activity Relationship
D005227:Fatty Acids; D005699:Galactosylceramides; D010647:Phenyl Ethers; D019920:Photoaffinity Labels; D011609:Psychosine; D003978:Diazomethane; D000581:Amidohydrolases; C096410:sphingolipid ceramide N-deacylase