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Literature summary extracted from

  • Zhou, K.; Peters, R.J.
    Electrostatic effects on (di)terpene synthase product outcome (2011), Chem. Commun. (Camb. ), 47, 4074-4080.
    View publication on PubMedView publication on EuropePMC

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
5.5.1.8 analysis of tertiary crystal structures of bornyl diphosphate synthase complexed with diphosphate and/or aza-analogs, mimicking various carbocations of the BPS catalyzed reaction Salvia officinalis

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
5.5.1.8 geranyl diphosphate Salvia officinalis cyclization (+)-bornyl diphosphate
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?
5.5.1.8 additional information Salvia officinalis (di)terpene synthases seem to mediate specific reaction outcomes, at least in part, by providing electrostatic effects to counteract those exerted by the diphosphate co-product. Role for the diphosphate anion co-product in the reaction catalyzed by monoterpene cyclases, such as bornyl diphosphate synthase ?
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?

Organism

EC Number Organism UniProt Comment Textmining
5.5.1.8 Salvia officinalis
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-
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Reaction

EC Number Reaction Comment Organism Reaction ID
5.5.1.8 geranyl diphosphate = (+)-bornyl diphosphate reaction mechanism, overview Salvia officinalis

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
5.5.1.8 geranyl diphosphate cyclization Salvia officinalis (+)-bornyl diphosphate
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?
5.5.1.8 additional information (di)terpene synthases seem to mediate specific reaction outcomes, at least in part, by providing electrostatic effects to counteract those exerted by the diphosphate co-product. Role for the diphosphate anion co-product in the reaction catalyzed by monoterpene cyclases, such as bornyl diphosphate synthase Salvia officinalis ?
-
?
5.5.1.8 additional information hydroxyl dipole stabilization of the specific carbocation formed by initial cyclization, enabling deprotonation of this early intermediate, whereas the lack of such stabilization, i.e. in the presence of an aliphatic side chain leads to carbocation migration towards the pyrophosphate co-product, resulting in a more complex reaction. The 7-aza-7,8-dihydrolimonene analogue is clearly bound backwards to enable aza-diphosphate ion-pairing, indicating that this is the thermodynamically favored binding mode for such a carbocation. The diphosphate co-product is tightly bound and may serve as a general acid/base during terpene synthase reactions without becoming reattached itself. Consistent with such tight binding is the stereospecificity of bornyl diphosphate formation by BPS, which reattaches the bornyl cation to the same oxygen of the diphosphate involved in the original diphosphate ester bond of the GPP substrate, indicating that the diphosphate anion remains in a fixed orientation during the catalyzed reaction Salvia officinalis ?
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?

Subunits

EC Number Subunits Comment Organism
5.5.1.8 More analysis of tertiary crystal structures of bornyl diphosphate synthase, the aza moiety is ion-paired with the diphosphate, whose position is essentially invariant Salvia officinalis

Synonyms

EC Number Synonyms Comment Organism
5.5.1.8 (di)terpene synthase
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Salvia officinalis
5.5.1.8 BPS
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Salvia officinalis