4.2.3.132: neoabietadiene synthase

This is an abbreviated version!
For detailed information about neoabietadiene synthase, go to the full flat file.

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Synonyms

abietadiene synthase, abietadiene/levopimaradiene synthase, AGAS, NAS, PtTPS-LAS, TPS-LAS

ECTree

     4 Lyases

         4.2 Carbon-oxygen lyases

             4.2.3 Acting on phosphates

                4.2.3.132 neoabietadiene synthase

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Results	in table
6	AA Sequence
3	Cloned(Commentary)
1	Crystallization (Commentary)
1	General Information
1	kcat/KM [mM/s]
4	KM Value [mM]
1	Localization
1	Metals/Ions
1	Molecular Weight [Da]
4	Organism
3	Pathway
1	pH Optimum
1	pI Value
20	Protein Variants
3	Purification (Commentary)
1	Reaction
4	Reference
1	Storage Stability
4	Substrates and Products (Substrate)
2	Subunits
8	Synonyms
1	Systematic Name
4	Turnover Number [1/s]

Substrates Products

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Substrates Products on EC 4.2.3.132 - neoabietadiene synthase

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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

(+)-copalyl diphosphate

?

Abies grandis

-

the enzyme converts geranylgeranyl diphosphate and the intermediate (+)-copalyl diphosphate to a nearly equal mixture of abietadiene (31%), levopimaradiene (34%), and neoabietadiene (28%), as well as to three minor products pimara-8(14),15-diene (3%), palustradiene (2%), and sandaracopimaradiene (2%)

440065

-

-

?

(+)-copalyl diphosphate

neoabietadiene + diphosphate

Abies grandis

Q38710

-

720053

-

-

?

additional information

?

-

2 entries

additional information

?

-

Abies grandis

-

abietadiene synthase catalyzes the cyclization and rearrangement of (E,E,E)-geranylgeranyl diphosphate to a mixture of abietadiene double-bond isomers. The enzyme is bifunctional: Protonation across the terminal 14-15 double bond of (E,E,E)-geranylgeranyl diphosphate followed by bicyclization and deprotonation, produces the stable intermediate (+)-copalyl diphosphate (CPP). Then the enzyme ionizes CPP to promote cyclization to the tricyclic perhydrophenanthrene backbone. However, this cyclization is further coupled to a 1,2-methyl migration, by means of intramolecular proton transfer within a pimarenyl intermediate, to generate the C13 isopropyl group characteristic of the abietane skeleton. Finally, deprotonation of the resulting abietenyl carbocation at one of three alternative positions (C7, C12, or C15) leads to the three principal olefin products abieta-7(8),13(14)-diene (abietadiene), abieta-8(14),12(13)-diene (levopimaradiene), and abieta-8(14)-13(15)-diene (neoabietadiene), respectively, as a function of pH

440068

-

-

?

additional information

?

-

Pinus taeda

-

the enzyme forms levopimaradiene (45.2%), abietadiene (27.6%), palustradiene (4.5%), and neoabietadiene (22.4%) from geranylgeranyl diphosphate, but shows no activity with geranyl diphosphate or farnesyl diphosphate

666567

-

-

?