Araki S, Satake M, Ando S, Hayashi A, Fujii N
J Biol Chem. 1986 Apr 15;261(11):5138-44.
The complete structure is proposed for a ceramide (Cer), bis(2-aminoethylphosphono)-pentaoside, isolated from the skin of Aplysia kurodai. This new phosphonoglycosphingolipid was purified using two systems of column chromatography on silicic acid. The purity of the glycolipid was confirmed by thin-layer chromatography, analysis of its composition, and proton magnetic resonance spectrometry. The component carbohydrates were glucose, galactose, N-acetylgalactosamine, and 3-O-methylgalactose. Most (90%) of the fatty acid was palmitic acid and the major sphingosine bases were octadeca-4-sphingenine (51%) and anteisononadeca-4-sphingenine (38%). 2-Aminoethylphosphonyl-6-galactose was identified after its partial hydrolysis. From studies by methanolysis, permethylation, mild acid hydrolysis, hydrogen fluoride treatment, chromium trioxide oxidation combined with thin-layer chromatography, gas liquid chromatography, gas chromatography-mass spectrometry, and proton magnetic resonance spectrometry, the structure of the glycolipid was concluded to be 3-OMeGal beta 1----3GalNAc alpha 1----36'-O-(2-aminoethylphosphonyl)-Gal alpha 1----2Gal beta 1----4Glc beta 1----1Cer.
从黑指纹海兔皮肤中分离出一种神经酰胺（Cer）——双（2-氨乙基膦酰基）戊糖苷，并提出了其完整结构。这种新的膦酰基糖鞘脂通过两种硅酸柱色谱系统进行纯化。通过薄层色谱、成分分析和质子磁共振光谱法确认了糖脂的纯度。组成碳水化合物为葡萄糖、半乳糖、N-乙酰半乳糖胺和3-O-甲基半乳糖。大部分（90%）脂肪酸为棕榈酸，主要鞘氨醇碱为十八碳-4-鞘氨醇（51%）和反式十九碳-4-鞘氨醇（38%）。2-氨乙基膦酰基-6-半乳糖经部分水解后得以鉴定。通过甲醇解、全甲基化、温和酸水解、氟化氢处理、三氧化铬氧化结合薄层色谱、气液色谱、气相色谱-质谱和质子磁共振光谱等研究，得出该糖脂的结构为3-OMeGalβ1----3GalNAcα1----36'-O-(2-氨乙基膦酰基)-Galα1----2Galβ1----4Glcβ1----1Cer。
