title: Artificial substrates for prenyltransferase.
abstract: Four out of 16 new allylic pyrophosphates synthesized were found to be artificial substrates for liver prenyltransferase (EC 2.5.1.1). These were the trans-and the cis-3-ethyl-3-methylallyl, the 3,3-diethylallyl and the (mixture of cis and trans) 3-methyl-3-n-propylallyl pyrophosphates. The products synthesized from these substrates and isopentenyl pyrophosphate were the appropriate homo- and bishomo-farnesyl pyrophosphates. Substitution of 3,3-dimethylallyl pyrophosphate at C-2 with a methyl group destroyed its reactivity with the enzyme. Neither the unsubstituted allyl pyrophosphate nor the cis- or trans-3-methylallyl pyrophosphate could be condensed with isopentenyl pyrophosphate. Thus the simplest allylic substrate for prenyltransferase is 3,3-dimethylallyl pyrophosphate.
mesh_terms: D000818:Animals; D002849:Chromatography, Gas; D011756:Diphosphates / Q000138:chemical synthesis; D005204:Farnesol; D008099:Liver / Q000201:enzymology; D013057:Spectrum Analysis; D013552:Swine; D014166:Transferases
chemical_list: D011756:Diphosphates; D005204:Farnesol; D014166:Transferases