Wedgwood J F, Warren C D, Jeanloz R W, Strominger J L
Proc Natl Acad Sci U S A. 1974 Dec;71(12):5022-6. doi: 10.1073/pnas.71.12.5022.
Fully acetylated chitobiose was treated with phosphoric acid to give a mixture of products from which 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta- D-glucopyranosyl)-3,6-di-O-acetyl-2-deoxy-alpha,beta- D-glucopyranosyl phosphate (Ac(3)GlcNAc-Ac(2)GlcNAc-P) was isolated by preparative thin layer chromatography. Treatment of this compound with P(1)-diphenyl P(2)-dolichyl pyrophosphate gave an acetylated pyrophosphate diester, which was purified chromatographically and deacetylated. The product, P(1)-di-N-acetylchitobiosyl P(2)-dolichyl pyrophosphate (Dol-P-P-GlcNAc-GlcNAc), was readily separated from P(1)-2-acetamido-2-deoxy-alpha-D-glucopyranosyl P(2)-dolichyl pyrophosphate (Dol-P-P-GlcNAc) by thin layer chromatography in several solvent systems. Addition of this compound to human lymphocyte membrane preparations led to the formation of a mannose-containing derivative which appears to be an oligosaccharide phospholipid, as judged by its behavior on DEAE-cellulose chromatography and by its hydrolysis to give an oligosaccharide containing more than four monosaccharide units.
将完全乙酰化的壳二糖用磷酸处理，得到产物混合物，通过制备型薄层色谱从中分离出2-乙酰氨基-4-O-(2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-β-D-吡喃葡萄糖基)-3,6-二-O-乙酰基-2-脱氧-α,β-D-吡喃葡萄糖基磷酸酯(Ac(3)GlcNAc-Ac(2)GlcNAc-P)。用P(1)-二苯基P(2)-多萜醇焦磷酸酯处理该化合物，得到一种乙酰化的焦磷酸二酯，将其进行色谱纯化并脱乙酰化。产物P(1)-二-N-乙酰壳二糖基P(2)-多萜醇焦磷酸酯(Dol-P-P-GlcNAc-GlcNAc)通过在几种溶剂系统中的薄层色谱很容易与P(1)-2-乙酰氨基-2-脱氧-α-D-吡喃葡萄糖基P(2)-多萜醇焦磷酸酯(Dol-P-P-GlcNAc)分离。将该化合物添加到人淋巴细胞膜制剂中导致形成一种含甘露糖的衍生物，根据其在DEAE-纤维素色谱上的行为以及其水解产生一种含有超过四个单糖单元的寡糖判断，该衍生物似乎是一种寡糖磷脂。
