Isolated from the bacterium Streptomyces clavuligerus. The 1-proR hydrogen atom of geranylgeranyl diphosphate is lost in the reaction. The enzyme also produces hydropyrenol, isoelisabethatriene and traces of other diterpenoids. cf. EC 4.2.3.202, hydropyrenol synthase, and EC 4.2.3.203, isoelisabethatriene synthase.
The expected taxonomic range for this enzyme is: Streptomyces clavuligerus
Isolated from the bacterium Streptomyces clavuligerus. The 1-proR hydrogen atom of geranylgeranyl diphosphate is lost in the reaction. The enzyme also produces hydropyrenol, isoelisabethatriene and traces of other diterpenoids. cf. EC 4.2.3.202, hydropyrenol synthase, and EC 4.2.3.203, isoelisabethatriene 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/l. 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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