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Information on EC 4.2.3.18 - abieta-7,13-diene synthase and Organism(s) Picea abies and UniProt Accession Q675L4

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EC Tree
     4 Lyases
         4.2 Carbon-oxygen lyases
             4.2.3 Acting on phosphates
                4.2.3.18 abieta-7,13-diene synthase
IUBMB Comments
Part of a bifunctional enzyme involved in the biosynthesis of abietadiene. See also EC 5.5.1.12, copalyl diphosphate synthase. Requires Mg2+.
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This record set is specific for:
Picea abies
UNIPROT: Q675L4
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The taxonomic range for the selected organisms is: Picea abies
The enzyme appears in selected viruses and cellular organisms
Synonyms
pdabs, pttps-las, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
(-)-abietadiene synthase
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-
-
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abietadiene cyclase
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-
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cyclase, abietadiene
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-
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PaLAS
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-
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(+)-copalyl diphosphate = abieta-7,13-diene + diphosphate
show the reaction diagram
reaction mechanism proceeds via water quenching of the abieta-8(14)-en-13-yl carbocation, resulting in 13-hydroxy-8(14)-abietene
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
cyclization
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elimination of diphosphate
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SYSTEMATIC NAME
IUBMB Comments
(+)-copalyl-diphosphate diphosphate-lyase [cyclizing, abieta-7,13-diene-forming]
Part of a bifunctional enzyme involved in the biosynthesis of abietadiene. See also EC 5.5.1.12, copalyl diphosphate synthase. Requires Mg2+.
CAS REGISTRY NUMBER
COMMENTARY hide
157972-08-2
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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
(+)-copalyl-diphosphate
(-)-abietadiene + levopimaradiene + neoabietadiene + palustradiene + diphosphate
show the reaction diagram
reaction intermediate is C8-sandaracopimaradienyl cation
bifunctional levopimaradiene/abietadiene synthase produces a mixture of diterpenes
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?
(+)-copalyl diphosphate
(+-)-13-hydroxy-8(14)-abietene + diphosphate
show the reaction diagram
-
-
initial product of the reaction, thermally unstable. Dehydration of the alcohol products of (+)-copalyl diphosphate, yielding the well established diterpene products levopimaradiene, abietadiene, neoabietadiene, and palustradiene, may occurr due to three conditions of the GC-MS analysis typically used for identification of diterpene synthase products: a hot injector, a hot oven temperature necessary for eluting the compounds, and the high temperature and high energy of the MS and its interface
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?
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
bifunctional levopimaradiene/abietadiene synthase
SwissProt
Manually annotated by BRENDA team
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
TPSD1_PICAB
859
0
98458
Swiss-Prot
other Location (Reliability: 1)
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
homology model of the second active site of enzyme based on the structure of 5-epiaristolochene synthase from Nicotiana tabacum, Protein Data Bank ID code 5EAT
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
A713S
products are isopimaradiene and sandaracopimaradiene
G651V
no change in product
V717L
no change in product
W679L/Y686H/A713S/V717L
products are isopimaradiene and sandaracopimaradiene
Y686H
no change in product
Y686H/A713S
main products are isopimaradiene and sandaracopimaradiene
Y686H/A713S A713S
main products are isopimaradiene and sandaracopimaradiene
Y686H/A713S/V717L
products are isopimaradiene and sandaracopimaradiene
additional information
swapping of residues 568–640 of isopimaradiene synhase to corresponding residues 560-632 of levopimaradiene/abietadiene synthase results in complete reversion of the product profiles of the two enzymes
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Keeling, C.I.; Weisshaar, S.; Lin, r.P.C.; Bohlmann, J.
Functional plasticity of paralogous diterpene synthases involved in conifer defense
Proc. Natl. Acad. Sci. USA
105
1085-1090
2008
Picea abies (Q675L4)
Manually annotated by BRENDA team
Keeling, C.I.; Madilao, L.L.; Zerbe, P.; Dullat, H.K.; Bohlmann, J.
The primary diterpene synthase products of Picea abies levopimaradiene/abietadiene synthase (PaLAS) are epimers of a thermally unstable diterpenol
J. Biol. Chem.
286
21145-21153
2011
Picea abies
Manually annotated by BRENDA team