Isomers of glucosaminylphospatiylglycerol in Bacillus megaterium.
1. The lipids of Bacillus megaterium were extracted and three lipids containing glucosamine were identified. One of these is not a phospholipid, but the other two, which differ in their chromatographic behaviour, contain phosphorus, glycerol, fatty acid and d-glucosamine in the molar proportions 1:2:2:1. 2. In both phosphoglycolipids, the fatty acids are bound in ester linkage, and both yield 2,5-anhydromannose and 3-sn-phosphatidyl-1'-sn-glycerol on treatment with sodium nitrite. 3. Both phosphoglycolipids were N-acetylated and, after removal of fatty acids by mild alkaline hydrolysis, in both cases N-acetylglucosamine was quantitatively released by beta-N-acetylhexosaminidase. 4. The glucosaminylglycerols derived from the two phosphoglycolipids by partial acid hydrolysis differ in their behaviour towards periodate. In one case 1 mole of periodate is rapidly consumed/mole of glucosaminylglycerol, but in the other case under identical conditions the consumption of periodate is negligible. 5. The phosphoglycolipids were identified as 1'-(1,2-diacyl-sn-glycero-3-phosphoryl)-3'-O-beta-(2-amino-2-deoxy-d-glucopyranosyl)-sn-glycerol and as 1'-(1,2-diacyl-sn-glycero-3-phosphoryl)-2'-O-beta-(2-amino-2-deoxy-d-glucopyranosyl)-sn-glycerol. 6. Both phosphoglycolipids are good substrates for phospholipase A: neither is a substrate for phospholipase C from Clostridium perfringens, and only the 3'-glucosaminide is a substrate for phospholipase D.
D001410:Bacillus megaterium / Q000032:analysis*; D002845:Chromatography; D003016:Clostridium perfringens; D005227:Fatty Acids / Q000032:analysis; D005944:Glucosamine / Q000032:analysis*; D005990:Glycerol / Q000032:analysis; D008055:Lipids / Q000032:analysis; D010504:Periodic Acid; D010740:Phospholipases; D010743:Phospholipids / Q000032:analysis*; D010758:Phosphorus / Q000032:analysis
D005227:Fatty Acids; D008055:Lipids; D010743:Phospholipids; D010504:Periodic Acid; D010758:Phosphorus; D010740:Phospholipases; D005944:Glucosamine; D005990:Glycerol