Abstract
Linoleic acid hydroperoxide isomerase from corn germ inverted the stereoconfiguration of its substrate. 9-D(S)-Hydroperoxy-trans-10,cis-12-octadecadienoic acid was converted to 10-oxo-9-L(R)-hydroxy-cis-12-octadecenoic acid. Presumably, the H2O solvent of OH− acted as a nucleophile. In the presence of another nucleophile, linoleate, the 9-D(S)-hydroperoxide was transformed into 9-L(R)-linoleoyloxy-10-oxo-cis-12-octadecenoic acid. The substitution of nucleophiles from the incubation solution and the inversion of stereoconfiguration at carbon-9 are consistent with a bimolecular nucleophilic substitution (SN2) mechanism.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Zimmerman, D.C., Biochem. Biophys. Res. Commun. 23:398 (1966).
Veldink, G.A., J.F.G. Vliegenthart, and J. Bolding, Biochem. J. 120:55 (1970).
Gardner, H.W., J. Lipid Res. 11:311 (1970).
Gardner, H.W., R. Kleiman, D.D. Christianson, and D. Weisleder, Lipids 10:602 (1975).
Veldink, G.A., J.F.G. Vliegenthart, and J. Boldingh, FEBS Lett. 7:188 (1970).
Gerritsen, M., G.A. Veldink, J.F.G. Vliegenthart, and J. Boldingh, FEBS Lett. 67:149 (1976).
Christianson, D.D., and H.W. Gardner, Lipids 10:448 (1975).
Gardner, H.W., and D. Weisleder, Lipids 5:678 (1970).
Morris, L.J., J. Chromatogr. 12:321 (1963).
Kleiman, R., and G.F. Spencer, J. Am. Oil Chem. Soc. 50:31 (1973).
Chan, H.W.-S., C.T. Costaras, F.A.A. Prescott, and P.A.T. Swoboda, Biochim. Biophys. Acta 398:347 (1975).
Morris, L.J., and M.L. Crouchman, Lipids 7:372 (1972).
Morris, L.J., and D.M. Wharry, Lipids 1:41 (1966).
Daly, J.W., D.M. Jerina, and B. Witkop, Experientia 28:1129 (1972).
Zimmerman, D.C., and B.A. Vick, Plant Physiol. 46:445 (1970).
Author information
Authors and Affiliations
Additional information
The mention of firm names or trade products does not imply that they are endorsed or recommended by the U.S. Department of Agriculture over other firms or similar products not mentioned.