Isolated from the bacterium Streptomyces clavuligerus. The 1-proR hydrogen atom of geranylgeranyl diphosphate is involved in a 1,3-hydride shift to the side-chain. The enzyme also produces hydropyrene, hydropyrenol, and traces of other diterpenoids. cf. EC 4.2.3.201, hydropyrene synthase, and EC 4.2.3.202, hydropyrenol synthase.
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Isolated from the bacterium Streptomyces clavuligerus. The 1-proR hydrogen atom of geranylgeranyl diphosphate is involved in a 1,3-hydride shift to the side-chain. The enzyme also produces hydropyrene, hydropyrenol, and traces of other diterpenoids. cf. EC 4.2.3.201, hydropyrene synthase, and EC 4.2.3.202, hydropyrenol synthase.
in wild-type, there is a great thermodynamic preference for hydropyrene and hydropyrenol formation. The synthesis of the isoelisabethatriene byproducts is under kinetic control. to IEs A and B as well as hydropyrene and hydropyrenol. In the reactions generating isoelisabethatrienes there is an exchange of two pi-bonds for sigma-bonds, resulting in a total exergonicity of -34.4 and -35.9 kcal/mol, respectively. The reactions to hydropyrene and hydropyrol replace four pi-bonds for sigma-bonds and share a common final carbocation, the exergonicity is -62.8 kcal/mol. These values reflect the energetics of exchanging pi-bonds for sigma-bonds
mutant displays a significantly enhanced yield of isoelisabethatriene A and B, with a concomitant reduction in hydroperene and hydropyrol production. M75F shows the highest isoelisabethatriene B yield observed
mutant displays a significantly enhanced yield of isoelisabethatriene A and B, with a concomitant reduction in hydroperene and hydropyrol production. M75L shows the highest isoelisabethatriene A yield observed
expression in Escherichia coli host gives a total terpene yield of mutant M75L of 41.91 mg/. Lipase catalysed chemo-enzymatic oxidation differentially transforms the isomers isoelisabethatriene A and B to the advanced pseudopterosin precursor erogorgiaene (yield: 69%) and the compound 1R-epoxy-elisabetha-5,14-diene (yield: 41%), respectively
Ringel, M.; Reinbold, M.; Hirte, M.; Haack, M.; Huber, C.; Eisenreich, W.; Masri, M.; Schenk, G.; Guddat, L.; Loll, B.; Kerr, R.; Garbe, D.; Brueck, T.
Towards a sustainable generation of pseudopterosin-type bioactives
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