Hashimoto Makoto, Hatanaka Yasumaru, Nabeta Kensuke
Department of Bioresource Science, Obihiro University of Agriculture and Veterinary Medicine, Inada-cho, Obihiro 080-8555, Hokkaido, Japan.
Bioorg Med Chem Lett. 2002 Jan 7;12(1):89-91. doi: 10.1016/s0960-894x(01)00669-2.
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.
报道了一种基于重氮丙啶的光反应性脂肪酸类似物的通用合成方法。关键步骤是重氮丙啶与卤代烷基酸酯的苯氧基烷基化反应。所描述的条件对于合成各种不同烷基长度的衍生物是可行的。这些脂肪酸衍生物是鞘脂神经酰胺N-脱酰基酶（SCDase）逆反应的受体，该酶催化鞘氨醇和脂肪酸缩合形成光反应性半乳糖神经酰胺。光反应性半乳糖神经酰胺也可以通过化学合成，即鞘氨醇与脂肪酸琥珀酰亚胺酯的缩合来制备，并且在辐照前后都能被抗半乳糖神经酰胺抗体识别。
