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Literature summary extracted from

  • Liu, M.; Chen, C.C.; Chen, L.; Xiao, X.; Zheng, Y.; Huang, J.W.; Liu, W.; Ko, T.P.; Cheng, Y.S.; Feng, X.; Oldfield, E.; Guo, R.T.; Ma, Y.
    Structure and function of a head-to-middle prenyltransferase: lavandulyl diphosphate synthase (2016), Angew. Chem. Int. Ed. Engl., 55, 4721-4724.
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

EC Number Cloned (Comment) Organism
2.5.1.69 recombinant expression of truncated mutant enzymes with 30, 50, or 55 N-terminal residues deleted. The DELTA30 and DELTA50 proteins are unstable but the DELTA55 protein is successfully expressed Lavandula x intermedia

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
2.5.1.69 purified recombinat DELTA55 LPPS enzyme mutant as dimeric apo-protein and with ligands bound, soaking of LPPS crystals with S-thiolo-dimethylallyl diphosphate and with S-thiolo-isopentenyldiphosphate, X-ray diffraction structure determination and analysis at 1.87 A resolution Lavandula x intermedia

Protein Variants

EC Number Protein Variants Comment Organism
2.5.1.69 H78N site-directed mutagenesis, inactive mutant Lavandula x intermedia
2.5.1.69 W100V site-directed mutagenesis, the mutant shows 15% of wild-type activity Lavandula x intermedia
2.5.1.69 Y139F site-directed mutagenesis, the mutant shows 62% of wild-type activity Lavandula x intermedia

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
2.5.1.69 Mg2+ required, activates Lavandula x intermedia

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.5.1.69 2 dimethylallyl diphosphate Lavandula x intermedia
-
 diphosphate + lavandulyl diphosphate
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.5.1.69 Lavandula x intermedia M4QSY7
-
-

Reaction

EC Number Reaction Comment Organism Reaction ID
2.5.1.69 2 dimethylallyl diphosphate = diphosphate + lavandulyl diphosphate the two dimethylallyl diphosphate molecules, both allylic diphosphates, condense via a so-called head-to-middle condensation to form the (C10) monterpene, lavandulyl diphosphate. The enzyme structure is similar to that of the bacterial cis-prenyl synthase, undecaprenyl diphosphate synthase, and contains an allylic site (S1) in which dimethylallyl diphosphate ionizes and a second site (S2) which houses the dimethylallyl diphosphate nucleophile. Both S-thiolo-dimethylallyl diphosphate and S-thiolo-isopentenyl diphosphate bind intact to S2, but are cleaved to (thio)diphosphate, in S1. His78 is essential for catalysis and is proposed to facilitate diphosphate release in S1, while the P1 phosphate in S2 abstracts a proton from the lavandulyl carbocation to form the LPP product, structure-based catalytic mechanism, overview Lavandula x intermedia
a

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.5.1.69 2 dimethylallyl diphosphate
-
 Lavandula x intermedia diphosphate + lavandulyl diphosphate
-
 ?

Synonyms

EC Number Synonyms Comment Organism
2.5.1.69 LPPS
-
 Lavandula x intermedia

General Information

EC Number General Information Comment Organism
2.5.1.69 additional information enzyme structure comparisons, ligand binding structure analysis, residue H78 is essential for catalysis, modelling, overview Lavandula x intermedia
2.5.1.69 additional information the enzyme structure is similar to that of the bacterial cis-prenyl synthase, undecaprenyl diphosphate synthase, and contains an allylic site (S1) in which dimethylallyl diphosphate ionizes and a second site (S2) which houses the dimethylallyl diphosphate nucleophile. Both S-thiolo-dimethylallyl diphosphate and S-thiolo-isopentenyl diphosphate bind intact to S2, but are cleaved to (thio)diphosphate, in S1. His78 is essential for catalysis and is proposed to facilitate diphosphate release in S1, while the P1 phosphate in S2 abstracts a proton from the lavandulyl carbocation to form the LPP product, structure-based mechanism, overview Lavandula x intermedia
2.5.1.69 physiological function the enzyme catalyzes the formation of C10 mononterpene lavandulyl diphosphate, the precursor of the fragrances (R)-lavandulol and (R)-lavandulyl acetate Lavandula x intermedia