Summary
The transfer of the phosphatidyl residue from egg phosphatidylcholine to primary alkanols catalyzed by phospholipase D was systematically investigated. It was demonstrated that 1) the chain length of the alkanols is of critical importance, e.g. transphosphatidylation does not occur to alkanols or alkandiols with more than six carbon atoms; 2) double or triple bonds in the acceptor molecule do not influence the transfer reaction; 3) fluorine is tolerated in the acceptor molecule, but the transfer rate decreases with increasing atomic weight from chlorine to iodine.
Synthetic phosphatidylcholines with large variations in the apolar part of the molecule, the phosphorylcholines of 1.2-diacyl-snglycerol, Acyl-propandiol-(1.3) and 1.2-cyclopentadecylmethylideneglycerol, have been successfully used in the transfer reaction. Transesterification is an attractive route for the synthesis of phospholipids differing in the polar part of the molecule.
Keywords
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsPreview
Unable to display preview. Download preview PDF.
References
Hanahan, D.J., and Chaikoff, J.L., J. Biol. Chem. 172 (1948) 191–198
Kates, M., Can. J. Biochem. Physiol. 34 (1956) 967–980
Benson, A.A., Freer, S., and Yang, S.F., (1965) 9th Intern. Conf. Biochem. Lipids, Noordwijk aan Zee, The Netherlands
Bartels, C.T., and van Deenen, L.L.M., Biochim. Biophys. Acta 125 (1966) 395–397
Yang, S.F., Freer, S., and Benson, A.A., J. Biol. Chem. 242 (1967) 477–484
Dawson, R.M.C., Biochem. J. 102 (1967) 205–210
Lennarz, W.J., Bonsen, P.P.M., and van Deenen, L.L.M., Biochemistry 6 (1967) 2307–2312
Jezyk, P.F., and Hughes, H.N., Biochim. Biophys. Acta 296 (1973) 24–33
Eibl, H., Arnold, D., Weltzien, H.U., and Westphal, O., Liebigs Ann. Chem. 709 (1967) 226–230
Eibl, H., and Westphal, O., Liebigs Ann. Chem. 738 (1970) 170–173
Eibl, H., and Nicksch, A., Chem. Phys. Lipids, submitted for publication
Davidson, F.M., and Long, C., Biochem. J. 69, (1958) 458–466
Lowry, 0.H., Rosebrough, N.J., Farr, A.L., and Randall, R.J., J. Biol. Chem. 193 (1951) 265–275
Singleton, W.S., Gray, M.S., Brown, M.L., and White, J.L., J. Am. Oil Chem. Soc. 42 (1965) 53–56
Eibl, H., and Westphal, O., Liebigs Ann. Chem. 709 (1967) 244–247
Eibl, H., and Lands, W.E.M., Anal. Biochem. 30 (1969) 51–57
Eibl, H., and Lands, W.E.M., Biochemistry 9 (1970) 423–428
Gould, E.S., in: Mechanismus und Struktur in der organischen Chemie, Verlag Chemie, Weinheim (1971) 47–50
Comfurius, P., and Zwaal, R.F.A., Biochim. Biophys. Acta 488 (1977) 36–42
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1978 Plenum Press, New York
About this chapter
Cite this chapter
Kovatchev, S., Eibl, H. (1978). The Preparation of Phospholipids by Phospholipase D. In: Gatt, S., Freysz, L., Mandel, P. (eds) Enzymes of Lipid Metabolism. Advances in Experimental Medicine and Biology, vol 101. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-9071-2_21
Download citation
DOI: https://doi.org/10.1007/978-1-4615-9071-2_21
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4615-9073-6
Online ISBN: 978-1-4615-9071-2
eBook Packages: Springer Book Archive