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Information on EC 4.2.3.140 - cis-abienol synthase

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EC Tree

4 Lyases

4.2 Carbon-oxygen lyases

4.2.3 Acting on phosphates

4.2.3.140 cis-abienol synthase

IUBMB Comments

Isolated from the plants Abies balsamea (balsam fir) and Nicotiana tabacum (tobacco) .

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4.2.3.140
diterpene
enterovirus
epidemic
mainland
seroprevalence
virus-like
solanaceae
coxsackievirus
pre-school
diterpenoids
abchs
seroepidemiology
habrochaites
trichome

The enzyme appears in viruses and cellular organisms

Reaction Schemes

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(13E)-8alpha-hydroxylabd-13-en-15-yl diphosphate

cis-abienol

diphosphate

Synonyms

ntabs, abcas, z-abienol synthase, show all synonyms

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SYNONYM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

AbCAS

AbdiTPS4

CAS

cis-abienol synthase

NtABS

TPS4

Z-abienol synthase

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REACTION

REACTION DIAGRAM

COMMENTARY

ORGANISM

UNIPROT

LITERATURE

(13E)-8alpha-hydroxylabd-13-en-15-yl diphosphate = cis-abienol + diphosphate

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PATHWAY SOURCE

PATHWAYS

KEGG

Biosynthesis of secondary metabolites, Diterpenoid biosynthesis

MetaCyc

cis-abienol biosynthesis

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SYSTEMATIC NAME

IUBMB Comments

(13E)-8alpha-hydroxylabd-13-en-15-yl-diphosphate-lyase (cis-abienol forming)

Isolated from the plants Abies balsamea (balsam fir) [1] and Nicotiana tabacum (tobacco) [2].

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SUBSTRATE

PRODUCT

REACTION DIAGRAM

ORGANISM

UNIPROT

COMMENTARY
(Substrate)

LITERATURE
(Substrate)

COMMENTARY
(Product)

LITERATURE
(Product)

Reversibility
r=reversible
ir=irreversible
?=not specified

(13E)-8alpha-hydroxylabd-13-en-15-yl diphosphate

cis-abienol + diphosphate

3 entries

additional information

4 entries

(13E)-8alpha-hydroxylabd-13-en-15-yl diphosphate

cis-abienol + diphosphate

Abies balsamea

746854

(13E)-8alpha-hydroxylabd-13-en-15-yl diphosphate

cis-abienol + diphosphate

Abies balsamea

H8ZM73

formation of cis-abienol proceeds via cyclization and hydroxylation at carbon C-8 of a postulated carbocation intermediate in the class II active site, followed by cleavage of the diphosphate group and termination of the reaction sequence without further cyclization in the class I active site

720008

(13E)-8alpha-hydroxylabd-13-en-15-yl diphosphate

cis-abienol + diphosphate

Nicotiana tabacum

720709

additional information

Abies balsamea

using (E,E,E)-geranylgeranyl diphosphate as a substrate AbdiTPS4 shows a unique single-peak product profile, which corresponds to cis-abienol 4

720008

additional information

Abies balsamea

H8ZM73

using (E,E,E)-geranylgeranyl diphosphate as a substrate AbdiTPS4 shows a unique single-peak product profile, which corresponds to cis-abienol 4

720008

additional information

Abies balsamea

bifunctional class I/II enzyme

720008

additional information

Abies balsamea

H8ZM73

bifunctional class I/II enzyme

720008

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NATURAL SUBSTRATE

NATURAL PRODUCT

REACTION DIAGRAM

ORGANISM

UNIPROT

COMMENTARY
(Substrate)

LITERATURE
(Substrate)

COMMENTARY
(Product)

LITERATURE
(Product)

REVERSIBILITY
r=reversible
ir=irreversible
?=not specified

(13E)-8alpha-hydroxylabd-13-en-15-yl diphosphate

cis-abienol + diphosphate

Abies balsamea

746854

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pH OPTIMUM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

7.2

assay at

7.8

assay at

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TEMPERATURE OPTIMUM

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

assay at

assay at

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ORGANISM

COMMENTARY

LITERATURE

UNIPROT

SEQUENCE DB

SOURCE

Abies balsamea

720008, 746854

H8ZM73

UniProt

brenda

Nicotiana tabacum

720709

brenda

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SOURCE TISSUE

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

SOURCE

brenda

predominantly expressed

720709

brenda

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LOCALIZATION

ORGANISM

UNIPROT

COMMENTARY

GeneOntology No.

LITERATURE

SOURCE

brenda

brenda

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GENERAL INFORMATION

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

malfunction

Nicotiana tabacum

ectopic expression of both NtCPS2 encoding a class-II terpene synthase that synthesizes 8-hydroxy-copalyl diphosphate and NtABS, driven by a trichomespecific promoter in transgenic Nicotiana sylvestris confers Z-abienol formation to this species, which does not normally produce it

720709

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UNIPROT

ENTRY NAME

ORGANISM

NO. OF AA

NO. OF TRANSM. HELICES

MOLECULAR WEIGHT[Da]

SOURCE

Sequence

H8ZM73 pBLAST

CAS_ABIBA

Abies balsamea

867

99539

Swiss-Prot

Show Sequence

G3CCC1 pBLAST

CABS_TOBAC

Nicotiana tabacum

792

91772

Swiss-Prot

Show Sequence

A0A2G9HJ45 pBLAST

A0A2G9HJ45_9LAMI

Handroanthus impetiginosus

745

86452

TrEMBL

Show Sequence

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CRYSTALLIZATION/commentary

ORGANISM

UNIPROT

LITERATURE

homology modeling based on PDB entry 3p5pA. The active site residues Asp-48, Leu617, Phe696, and Gly723 are potentially important for the specificity

Abies balsamea

720008

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PROTEIN VARIANTS

ORGANISM

UNIPROT

COMMENTARY

LITERATURE

D402A/D404A

Abies balsamea

monofunctional class II protein variant, complete loss of enzymatic activity with geranylgeranyl diphosphate as substrate; mutation results in complete loss of activity

720008

D621A

Abies balsamea

monofunctional class I protein variant, mutant produces trace amounts of copalyl diphosphate plus labda-13-en-8,15-diol

720008

additional information

Abies balsamea

lab-scale cultivation and pilot-scale cultivation setup of transgenic cell wall-deficient Chlamydomonas reinhardtii strain TN72-TPS4 recombinantly expressing enzyme TPS4, for establishment of industrial production of abietol, method evaluation, overview

746854

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PURIFICATION/commentary

ORGANISM

UNIPROT

LITERATURE

using Ni-NTA chromatography

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CLONED/commentary

ORGANISM

UNIPROT

LITERATURE

gene TPS4, recombinant expression in a cell wall-deficient Chlamydomonas reinhardtii strain TN72-TPS4 in chloroplasts, pilot-scale cultivation setup, method overview

Abies balsamea

746854

recombinantly expressed in Escherichia coli

Abies balsamea

720008

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REF.

AUTHORS

TITLE

JOURNAL

VOL.

PAGES

YEAR

ORGANISM (UNIPROT)

PUBMED ID

SOURCE

720008

Zerbe, P.; Chiang, A.; Yuen, M.; Hamberger, B.; Hamberger, B.; Draper, J.A.; Britton, R.; Bohlmann, J.

Bifunctional cis-abienol synthase from Abies balsamea discovered by transcriptome sequencing and its implications for diterpenoid fragrance production

J. Biol. Chem.

287

12121-12131

2012

Abies balsamea, Abies balsamea (H8ZM73)

22337889

brenda

720709

Sallaud, C.; Giacalone, C.; Toepfer, R.; Goepfert, S.; Bakaher, N.; Roesti, S.; Tissier, A.

Characterization of two genes for the biosynthesis of the labdane diterpene Z-abienol in tobacco (Nicotiana tabacum) glandular trichomes

Plant J.

1-17