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Chemical Compound Review:

AC1L47V5 (3,7-dimethylocta-1,6-dien-3- yloxy-hydroxy...

Synonyms: C05308, 16789-26-7, Linalyl diphosphate, Linalyl pyrophosphate, Linalool pyrophosphate

Satterwhite, D.M. et al., Savage, T.J. et al., Croteau, R.

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High impact information on Linaloyl diphosphate

The residual linalyl pyrophosphate was isolated and enzymatically hydrolyzed to the free alcohol, linalool, which was resolved by chiral phase capillary gas-liquid chromatography of the derived threo and erythro mixture of 1,2-epoxides [1].
Thus, like monoterpene synthases from herbaceous angiosperms, monoterpene synthases from lodgepole pine appear to catalyze both the stereospecific isomerization of geranyl pyrophosphate to linalyl pyrophosphate and the subsequent cyclization of this enzyme-bound intermediate to multiple, stereochemically related monoterpene olefin isomers [2].

Biological context of Linaloyl diphosphate

Conversion of geranyl pyrophosphate to cyclic monoterpenes is considered to involve the preliminary isomerization of this acyclic precursor to enzyme-bound linalyl pyrophosphate and the cyclization of this tertiary intermediate [3].

References

Biosynthesis of monoterpenes. Enantioselectivity in the enzymatic cyclization of linalyl pyrophosphate to (-)-endo-fenchol. Satterwhite, D.M., Wheeler, C.J., Croteau, R. J. Biol. Chem. (1985) [Pubmed]
Monoterpene synthases from gymnosperms and angiosperms: stereospecificity and inactivation by cysteinyl- and arginyl-directed modifying reagents. Savage, T.J., Ichii, H., Hume, S.D., Little, D.B., Croteau, R. Arch. Biochem. Biophys. (1995) [Pubmed]
Evidence for the ionization steps in monoterpene cyclization reactions using 2-fluorogeranyl and 2-fluorolinalyl pyrophosphates as substrates. Croteau, R. Arch. Biochem. Biophys. (1986) [Pubmed]

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