Information on EC 4.2.3.51 - beta-phellandrene synthase (neryl-diphosphate-cyclizing)

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The expected taxonomic range for this enzyme is: Solanum lycopersicum

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EC NUMBER
COMMENTARY hide
4.2.3.51
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RECOMMENDED NAME
GeneOntology No.
beta-phellandrene synthase (neryl-diphosphate-cyclizing)
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
neryl diphosphate = beta-phellandrene + diphosphate
show the reaction diagram
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
trichome monoterpenes biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
neryl-diphosphate diphosphate-lyase [cyclizing; beta-phellandrene-forming]
The enzyme from Solanum lycopersicum has very poor affinity with geranyl diphosphate as substrate. Catalyses the formation of the acyclic myrcene and ocimene as major products in addition to beta-phellandrene [1].
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
transgenic fruits overexpressing isoform PHS1 produce only small amounts of GPP-derived monoterpene products. Neryl diphosphate synthase NDPS1 coexpression with PHS1 results in a monoterpene blend, including beta-phellandrene, similar to that produced from NPP by PHS1 in vitro and in trichomes. Fruits coexpressing both PHS1 and NDPS1 show recovery of lycopene levels compared to NDPS1 fruits. In vitro assays demonstrate that NPP serves as an inhibitor of geranylgeranyl diphosphate synthase. Monoterpenes produced in fruits coexpressing both PHS1 and NDPS1 contribute to direct plant defense negatively affecting feeding behavior of the herbivore Helicoverpa zea and displaying antifungal activity against Botrytis cinerea
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
5 neryl diphosphate
5 diphosphate + alpha-phellandrene + beta-phellandrene + alpha-terpinene + beta-terpinene + limonene
show the reaction diagram
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main product is beta-phellandrene. The profile of monoterpenes produced by PHS1 is identical with the monoterpenes found in type VI glandular trichome. In tomato glands, neryl diphosphate serves as a precursor for the synthesis of monoterpenes
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?
neryl diphosphate
diphosphate + beta-phellandrene + alpha-terpinene + beta-terpinene + limonene + alpha-phellandrene
show the reaction diagram
neryl diphosphate most likely ionizes to a neryl cation, which can further isomerize to an alpha-terpinyl cation. Further transformations of this cyclic intermediate can eventually yield all observed products of PHS1
the main product is beta-phellandrene
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?
additional information
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
5 neryl diphosphate
5 diphosphate + alpha-phellandrene + beta-phellandrene + alpha-terpinene + beta-terpinene + limonene
show the reaction diagram
C1K5M3
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main product is beta-phellandrene. The profile of monoterpenes produced by PHS1 is identical with the monoterpenes found in type VI glandular trichome. In tomato glands, neryl diphosphate serves as a precursor for the synthesis of monoterpenes
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?
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0091
neryl diphosphate
pH 8.0, 30°C
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4.1
neryl diphosphate
pH 8.0, 30°C
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
451.5
neryl diphosphate
pH 8.0, 30°C
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
type VI glandular trichome, highly expressed
Manually annotated by BRENDA team
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
the complete ORF of PHS1 encodes a plastid transit peptide, construction of an ORF of PHS1 that begins at Met45 and includes a His-tag extension at the N-terminus, expression in Eschreichia coli
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
agriculture
monoterpenes produced in fruits overexpressing both isoform PHS1 and neryl diphsphate synthase NDPS1 contribute to direct plant defense negatively affecting feeding behavior of the herbivore Helicoverpa zea and displaying antifungal activity against Botrytis cinerea
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LINKS TO OTHER DATABASES (specific for EC-Number 4.2.3.51)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
InterPro (database of protein families, domains and functional sites)