Acylation of alkyllysophospholipids by Fischer sarcoma microsomes.

Acylation of alkyllysophospholipids in most cells occurs by: (a) CoA-independent transacylation, (b) CoA-dependent transacylation, and (c) acyl-CoA-dependent acylation. Using a recently developed high-performance liquid chromatography method, we have investigated the factors that influence the molecular species composition of the acylated products formed via these pathways with 1-hexadecyl-2-lyso-sn-glycero-3-phosphocholine (alkyllyso-GPC) or 1-hexadecyl-2-lyso-sn-glycero-3-phospho-ethanolamine (alkyllyso-GPE) as substrates for the enzymes in Fischer R-3259 sarcoma microsomes. We found that short incubation times and low substrate concentrations favored the formation of polyunsaturated molecular species, i.e., 16:0-22:6, 16:0-22:5 (n - 3), and 16:0-20:4. Also, in agreement with results from other systems, CoA-independent transacylation produced a high percentage of polyunsaturated molecular species; acyl-CoA-dependent acylations generated the least polyunsaturated molecular species and CoA-dependent transacylation gave intermediate values. Furthermore, no substrate selectivity occurred with respect to alkyl chain lengths of alkyllyso-GPE; similar molecular species composition was obtained with either hexadecyllyso-GPE or octadecyllyso-GPE as substrates. Responses to N-ethylmaleimide inhibition and heat inactivation as well as pH optima suggest the same enzyme catalyzes the CoA-independent transacylation of both alkyllyso-GPC and alkyllyso-GPE.