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Search The CSA
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Catalytic Site Atlas

CSA LITERATURE entry for 1n20

E.C. namebornyl diphosphate synthase
SpeciesSalvia officinalis (Garden sage)
E.C. Number (IntEnz) 5.5.1.8
CSA Homologues of 1n20There are 15 Homologs
CSA Entries With UniProtID O81192
CSA Entries With EC Number 5.5.1.8
PDBe Entry 1n20
PDBSum Entry 1n20
MACiE Entry M0259

Literature Report

IntroductionBoronyl diphosphate synthase catalyses the conversion of geranyl diphosphate to boronyl diphosphate. It is a member of the monoterpene synthases, a group of enzymes that catalyse the metal-dependent cyclisation of geranyl diphosphate to a variety of monoterpene products via carbocation intermediates.
MechansimBoronyl diphosphate synthase catalyses its reaction by promoting ionisation of the substrate and subsequently using both the departed pyrophosphate group and cation-pi interactions from aromatic residues to stabilise and orientate carbocation intermediates. Initial substrate ionisation is promoted by three Mg2+ ions that stabilise the departing pyrophosphate leaving group. Recapture of the pyrophosphate at C3 to give (3R)-linalyl diphosphate allows rotation around the C2-C3 bond. Re-ionisation now facilitates SN' cyclisation to give the (4R)-alpha-terpinyl cation. The C8 carbocation is likely to be stabilised by cation-pi interactions involving Phe 578 and Trp 323. Further anti-Markovnikov cyclisation gives the 2-boronyl cation that is quenched by pyrophosphate to yield the final product.
Reaction

Catalytic Sites for 1n20

Annotated By Reference To The Literature - Site 1 (Perform Site Search)
ResidueChainNumberUniProtKB NumberFunctional PartFunctionTargetDescription
PheA578578macie:sideChainProposed to stabilise accumulation of positive charge on C8 carbocation using cation-pi interactions.
TrpA323323macie:sideChainProposed to stabilise accumulation of positive charge on C8 carbocation using cation-pi interactions.

Annotated By Reference To The Literature - Site 2 (Perform Site Search)
ResidueChainNumberUniProtKB NumberFunctional PartFunctionTargetDescription
PheB578578macie:sideChainProposed to stabilise accumulation of positive charge on C8 carbocation using cation-pi interactions.
TrpB323323macie:sideChainProposed to stabilise accumulation of positive charge on C8 carbocation using cation-pi interactions.

Literature References

Notes:
Whittington DA
Bornyl diphosphate synthase: structure and strategy for carbocation manipulation by a terpenoid cyclase.
Proc Natl Acad Sci U S A 2002 99 15375-15380
PubMed: 12432096
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