Nature 217, 35 - 37 (06 January 1968); doi:10.1038/217035a0

Conformational Relationship between the O–C–C–N⁺ System of Phospholipids and Substrates of Muscarinic and Cholinergic Systems

M. SUNDARALINGAM

Department of Chemistry, Case Western Reserve University, Cleveland, Ohio

The O–C–C–N⁺ system is a common structural feature of phospholipids and nerve amines and it displays the gauche conformation about the carbon–carbon bond. The characteristic gauche conformation is probably associated with the biological activity of the phospholipids and the nerve amines. The close structural relationship between the phospholipid components and acetylcholine suggests that the lecithins and the sphingomyelins of cell membranes may be competitive inhibitors and sites of concentration of acetylcholinesterase.

1. Sundaralingam, M. , and Jensen, L. H. , Science, 150, 1035 (1965). | PubMed | ISI | ChemPort |
2. Shefter, E. , and Kennard, O. , Science, 153, 1389 (1966). | PubMed | ISI | ChemPort |
3. Sutor, D. J. , J. Chem. Soc., 1105 (1963).
4. Abrahamson, S. , and Pascher, I. , Acta Cryst., 21, 79 (1966). | ISI |
5. Jellinek, F. , Acta Cryst., 10, 277 (1957). | Article | ISI | ChemPort |
6. Senko, M. E. , and Templeton, D. H. , Acta Cryst., 13 281 (1960). | Article | ISI | ChemPort |
7. Sörum, H. , Acta Chem. Scand., 13, 345 (1959).
8. Canepa, F. G. , Pauling, P. , and Sörum, H. , Nature, 210, 907 (1966). | Article | PubMed | ISI | ChemPort |
9. Stora, C. , Bull. Soc. Chim., 199, 867 (1949).
10. Stora, C. , Bull. Soc. Chim., 200, 874 (1949).
11. Kraut, J. , Acta Cryst., 14, 1146 (1961). | Article | ISI | ChemPort |
12. McCallum, G. H. , Robertson, J. M. , and Sim, G. A. , Nature, 184, 1864 (1959).
13. Shoemaker, D. P. , Barieau, R. E. , Donohue, J. , and Lu, C. S. , Acta Cryst., 6, 241 (1953). | Article | ISI | ChemPort |
14. Shoemaker, D. P. , Donohue, J. , Shoemaker, V. , and Corey, R. D. , J. Amer. Chem. Soc., 72, 2328 (1950). | Article | ISI | ChemPort |
15. Culvenor, C. C. J. , and Ham, N. S. , Chem. Commun., No. 15, 537 (1966).
16. Tammelin, L. E. , Arkiv Kemi, 12, 287 (1958); Svensk Kem Tidskr., 70, 157 (1958). | ISI | ChemPort |
17. Wilson, I. B. , in The Enzymes (edit. by Boyer, P. D., Lardy, H., and Myrbäck, K.), 4, 501 (Academic Press, New York, 1960).
18. Foldes, F. F. , van Hees, G. , Davis, D. L. , and Shannor, S. P. , J. Pharmacol., 122, 457 (1958). | ISI | ChemPort |
19. Wilson, I. B. , and Quan, C. , Arch. Biochem. Biophys., 73, 131 (1958). | Article | PubMed | ISI | ChemPort |
20. Okaya, Y. , Acta Cryst., 21, 726 (1966). | Article | ISI | ChemPort |
21. Okaya, Y. , Acta Cryst., 21, A124 (1966).