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J. Biol. Chem., Vol. 255, Issue 3, 1074-1079, 02, 1980

The mechanism of ether bond formation in O-alkyl lipid synthesis

SJ Friedberg, DM Gomillion and PL Stotter

O-Alkyl dihydroxyacetone phosphate is formed enzymatically from acyl dihydroxyacetone phosphate and a long chain fatty alcohol. This reaction is accompanied by stereospecific exchange of the pro-R hydrogen of carbon 1 (carbon 1 of all compounds corresponds to carbon 1 of sn-glycerol) of the dihydroxyacetone phosphate moiety with retention of configuration. In the present investigation, data are provided to show that the initial loss of hydrogen from carbon 1 of acyl dihydroxyacetone phosphate does not depend on the presence of the fatty alcohol. In addition, the occurrence of a Schiff base between enzyme and acyl dihydroxyacetone phosphate, comparable to the fructose-1,6- diphosphate aldolase reaction, could not be demonstrated. It is concluded that the formation of 1-O-alkyl dihydroxyacetone phosphate via the formation of intermediate 1-O-acyl endiol and 1-O-alkyl endiol is a likely mechanism.
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				E. C. J. M. de Vet, Y. H. A. Hilkes, M. W. Fraaije, and H. van den Bosch Alkyl-dihydroxyacetonephosphate Synthase. PRESENCE AND ROLE OF FLAVIN ADENINE DINUCLEOTIDE J. Biol. Chem., February 25, 2000; 275(9): 6276 - 6283. [Abstract] [Full Text] [PDF]