来自莱氏无胆甾原体B株脂质的甘油磷酸二葡糖二甘油酯的结构

The structure of a glycerylphosphoryldiglucosyl diglyceride from the lipids of Acholeplasma laidlawii strain B.

Shaw N, Smith P F, Verheij H M

Biochem J. 1972 Aug;129(1):167-73. doi: 10.1042/bj1290167.

Abstract

The phosphatidylglucose structure proposed previously (Smith & Henrikson, 1965) for the glucose-containing phospholipid from Acholeplasma laidlawii is incorrect. 2. The structure now proposed is 3-(sn-glycerol-3-phosphoryl-6'-[O-alpha-d-glucopyranosyl-(1-->2)-O-alpha-d-glucopyranosyl])- sn-1,2-diglyceride, a new type of bacterial lipid. 3. Deacylation of the lipid gave a single water-soluble phosphate ester which could be distinguished on chromatography from synthetic samples of glucosylphosphorylglycerols. 4. Hydrolysis of the lipid with alkali gave a mixture of fatty acids, glycerol 2-phosphate, sn-glycerol 3-phosphate and O-alpha-d-glucopyranosyl-(1-->2)-O-alpha- d-glucopyranosyl-(1-->1)-d-glycerol. 5. The lipid was unaffected on incubation with phospholipases A, C and D. 6. Diglucosyl diglyceride was isolated after treatment of the lipid with 60% HF, establishing the location of the fatty acid residues. 7. Periodate oxidation studies showed that the sn-glycerol 3-phosphate was esterified to the 6-hydroxyl group of one of the glucose residues in diglucosyl diglyceride.

摘要

先前（史密斯和亨里克森，1965年）提出的关于莱氏无胆甾原体含葡萄糖磷脂的磷脂酰葡萄糖结构是不正确的。2. 现在提出的结构是3-(sn-甘油-3-磷酸-6'-[O-α-D-吡喃葡萄糖基-(1→2)-O-α-D-吡喃葡萄糖基])-sn-1,2-二甘油酯，一种新型的细菌脂质。3. 该脂质的脱酰作用产生了一种单一的水溶性磷酸酯，在色谱分析中可与葡萄糖基磷酸甘油的合成样品区分开来。4. 用碱水解该脂质得到脂肪酸、甘油2-磷酸、sn-甘油3-磷酸和O-α-D-吡喃葡萄糖基-(1→2)-O-α-D-吡喃葡萄糖基-(1→1)-D-甘油的混合物。5. 该脂质在与磷脂酶A、C和D孵育时不受影响。6. 用60%的氢氟酸处理该脂质后分离出二葡萄糖基二甘油酯，确定了脂肪酸残基的位置。7. 高碘酸盐氧化研究表明，sn-甘油3-磷酸酯与二葡萄糖基二甘油酯中一个葡萄糖残基的6-羟基酯化。