MacDonald D L, Patt L M, Hakomori S
J Lipid Res. 1980 Jul;21(5):642-5.
Some simplified and efficient procedures are described for the following chemical modifications of glycophingolipids. 1) The olefinic bond of the ceramide moiety of the acetylated glycolipid was quantitatively oxidized with osmium tetroxide and periodic acid. Treatment of the resulting glycolipid aldehyde with sodium methodixe resulted in the release of the intact oligosaccharide. The yield of oligosaccharides under the new conditions was much higher than previously found. 2) The olefinic bond was also oxidized to a carboxyl function by either of two methods: a) the aldehyde group resulting from the above oxidation was further oxidized with performic acid; and b) the olefinic bond of the fully acetylated glycolipid was oxidized directly to the acid by potassium permanganate in acetone. 3) The methyl ester of the carboxyl group of the sialic acid in gangliosides can be formed with diazomethane in methanol-ether after treatment of the gangliosides with Dowex-50 (H+ form). Possible uses of these glycolipid modifications are discussed.
本文描述了一些用于糖鞘脂以下化学修饰的简化高效方法。1）用四氧化锇和高碘酸对乙酰化糖脂的神经酰胺部分的烯键进行定量氧化。用甲酸钠处理所得的糖脂醛，可释放出完整的寡糖。新条件下寡糖的产率比以前高得多。2）烯键也可通过以下两种方法之一氧化为羧基：a）上述氧化产生的醛基用过甲酸进一步氧化；b）完全乙酰化糖脂的烯键在丙酮中被高锰酸钾直接氧化为酸。3）在用Dowex - 50（H +型）处理神经节苷脂后，可在甲醇 - 乙醚中用重氮甲烷形成神经节苷脂中唾液酸羧基的甲酯。讨论了这些糖脂修饰的可能用途。
