The structure of a glycerylphosphoryldiglucosyl diglyceride from the lipids of Acholeplasma laidlawii strain B.
1. 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.
D000128:Acholeplasma laidlawii / Q000032:analysis; D000215:Acylation; D002854:Chromatography, Paper; D002855:Chromatography, Thin Layer; D005227:Fatty Acids / Q000378:metabolism; D005989:Glycerides / Q000032:analysis; D005994:Glycerophosphates / Q000032:analysis; D006017:Glycolipids / Q000032:analysis*; D006858:Hydrofluoric Acid; D006868:Hydrolysis; D008956:Models, Chemical; D009174:Mycoplasma / Q000032:analysis*; D010084:Oxidation-Reduction; D010504:Periodic Acid; D010740:Phospholipases; D010743:Phospholipids / Q000032:analysis*
D005227:Fatty Acids; D005989:Glycerides; D005994:Glycerophosphates; D006017:Glycolipids; D010743:Phospholipids; D010504:Periodic Acid; D010740:Phospholipases; D006858:Hydrofluoric Acid