Evidence for the presence of water within the hydrophobic core of membranes.
The photoreactive ganglioside derivative N-diazirinyl-lyso-GM1 was incorporated into liposomes and calf brain microsomes. After photoactivation at 350 nm it was found to dimerize with phospholipids such as phosphatidylcholine and phosphatidylserine and with cholesterol. The predominant covalent reaction product, however, was the alcohol, resulting from the reaction with water. It amounted to about 45% of the covalent reaction products in calf brain microsomes and to about 58% in pure phosphatidylcholine liposomes. Based on the temperature dependence of the photoreaction of N-diazirinyl-lyso-GM1 in liposomes consisting of 1,2-dipalmitoyl-sn-glycero-3-phosphoryl-choline or 1,2-distearoyl-sn-glycero- 3-phosphorylcholine and on affinity labeling experiments with cholera toxin we propose that the predominant reaction of N-diazirinyl-lyso-GM1 with water is due to the presence of water within the hydrophobic core of artificial and biological membranes.
Meier
E M
EM
Institute of Organic Chemistry and Biochemistry, University of Bonn, F.R.G.
Schummer
D
D
Sandhoff
K
K
D015060:1,2-Dipalmitoylphosphatidylcholine / Q000378:metabolism; D000818:Animals; D002417:Cattle; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D002772:Cholera Toxin / Q000378:metabolism; D005677:G(M1) Ganglioside / Q000031:analogs & derivatives / Q000737:chemistry / Q000378:metabolism; D005732:Gangliosides / Q000378:metabolism; D008081:Liposomes / Q000378:metabolism*; D008566:Membranes / Q000378:metabolism*; D008823:Micelles; D010713:Phosphatidylcholines / Q000378:metabolism; D010777:Photochemistry; D014316:Tritium; D014867:Water / Q000737:chemistry / Q000378:metabolism*
D005732:Gangliosides; D008081:Liposomes; D008823:Micelles; D010713:Phosphatidylcholines; D014867:Water; D014316:Tritium; C067340:5-(4-(3-(trifluromethyl)diazirinyl)phenyl)pentanoyl-lyso-G(M1) ganglioside; D015060:1,2-Dipalmitoylphosphatidylcholine; D005677:G(M1) Ganglioside; D002772:Cholera Toxin; C010942:1,2-distearoyllecithin