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Chemical Compound Review:

AC1NQZD5 [[(E)-5-[(1R,4aS,8aS)-5,5,8a- trimethyl-2...

Synonyms: CHEBI:30939, LMPR0104030002, C11901, Copalyl diphosphate, Labdadienyl diphosphate

Tudzynski, B. et al., Peters, R.J. et al., Yamaguchi, S. et al., Kawaide, H. et al., Chang, C.W. et al., et al.

Kawaide, Imai, Sassa, Kamiya,

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High impact information on Copalyl diphosphate

The first reaction, protonation-initiated cyclization, converts the universal diterpene precursor geranylgeranyl diphosphate to the stable bicyclic intermediate copalyl diphosphate [1].
The deduced amino acid sequence shared 24 and 21% identity with maize copalyl diphosphate synthase and pumpkin ent-kaurene synthase, respectively [2].
The reaction proceeds at two active sites by way of the intermediate, copalyl diphosphate (9) [3].
Previous biochemical studies have suggested that the ga2 mutant is impaired in the conversion of copalyl diphosphate to ent-kaurene, which is catalyzed by ent-kaurene synthase (KS) [4].
The Arabidopsis GA1 gene encodes copalyl diphosphate synthase, which catalyzes the first committed step in the gibberellin biosynthetic pathway [5].

Gene context of Copalyl diphosphate

Next to the two P450 monooxygenase genes, a putative geranylgeranyl diphosphate synthase gene, the copalyl diphosphate synthase gene, which is the first specific gene of the gibberellin pathway, and a third P450 monooxygenase gene were identified [6].

References

Abietadiene synthase catalysis: mutational analysis of a prenyl diphosphate ionization-initiated cyclization and rearrangement. Peters, R.J., Croteau, R.B. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
Ent-kaurene synthase from the fungus Phaeosphaeria sp. L487. cDNA isolation, characterization, and bacterial expression of a bifunctional diterpene cyclase in fungal gibberellin biosynthesis. Kawaide, H., Imai, R., Sassa, T., Kamiya, Y. J. Biol. Chem. (1997) [Pubmed]
Mechanism of abietadiene synthase catalysis: stereochemistry and stabilization of the cryptic pimarenyl carbocation intermediates. Ravn, M.M., Peters, R.J., Coates, R.M., Croteau, R. J. Am. Chem. Soc. (2002) [Pubmed]
The GA2 locus of Arabidopsis thaliana encodes ent-kaurene synthase of gibberellin biosynthesis. Yamaguchi, S., Sun, T., Kawaide, H., Kamiya, Y. Plant Physiol. (1998) [Pubmed]
Characterization of cis-regulatory regions responsible for developmental regulation of the gibberellin biosynthetic gene GA1 in Arabidopsis thaliana. Chang, C.W., Sun, T.P. Plant Mol. Biol. (2002) [Pubmed]
Gibberellin biosynthetic pathway in Gibberella fujikuroi: evidence for a gene cluster. Tudzynski, B., Hölter, K. Fungal Genet. Biol. (1998) [Pubmed]

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