Acis-prenyltransferase fromMethanosarcina acetivoranscatalyzes both head-to-tail and nonhead-to-tail prenyl condensation

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Cis-prenyltransferase usually consecutively catalyzes the head-to-tail condensation reactions of isopentenyl diphosphate to allylic prenyl diphosphate in the production of (E,Z-mixed) polyprenyl diphosphate, which is the precursor of glycosyl carrier lipids. Some recently discovered homologs of the enzyme, however, catalyze the nonhead-to-tail condensation reactions between allylic prenyl diphosphates. In this study, we characterize a cis-prenyltransferase homolog from a methanogenic archaeon, Methanosarcina acetivorans, to obtain information on the biosynthesis of the glycosyl carrier lipids within it. This enzyme catalyzes both head-to-tail and nonhead-to-tail condensation reactions. The kinetic analysis shows that the main reaction of the enzyme is consecutive head-to-tail prenyl condensation reactions yielding polyprenyl diphosphates, while the chain lengths of the major products seem shorter than expected for the precursor of glycosyl carrier lipids. On the other hand, a subsidiary reaction of the enzyme, i.e., nonhead-to-tail condensation between dimethylallyl diphosphate and farnesyl diphosphate, gives a novel diterpenoid compound, geranyllavandulyl diphosphate.Cis-prenyltransferase catalyzes consecutive head-to-tail condensation of isopentenyl diphosphate with prenyl diphosphate to produce the precursor of glycosyl carrier lipid. We found that a cis-prenyltransferase homolog from Methanosarcina acetivorans catalyzes nonhead-to-tail condensation between farnesyl diphosphate and dimethylallyl diphosphate, in addition to the typical cis-prenyltransferase reaction. The kinetics and product analysis of the reactions were performed to infer its physiological roles.

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