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.
journal_name
Bioorg Med Chem Lettjournal_title
Bioorganic & medicinal chemistry lettersauthors
Hashimoto M,Hatanaka Y,Nabeta Kdoi
10.1016/s0960-894x(01)00669-2subject
Has Abstractpub_date
2002-01-07 00:00:00pages
89-91issue
1eissn
0960-894Xissn
1464-3405pii
S0960894X01006692journal_volume
12pub_type
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