Substrate specificities of farnesyl diphosphate synthases from Bacillus stearothermophilus and porcine liver with cyclic substrate homologs

We investigated the substrate specificity of farnesyl diphosphate (FPP) synthase derived from Bacillus stearothermophilus and porcine liver by examining the reactivities of two cyclic substrate homologs, cyclohexylideneethyl diphosphate and cyclohexenylethyl diphosphate. Reaction of geranyl diphosph...

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Bibliographic Details
Published in:Journal of molecular catalysis. B, Enzymatic Enzymatic, 2009-10, Vol.60 (3), p.186-190
Main Authors: Nagaki, Masahiko, Kanno, Hiroshi, Musashi, Tohru, Shimizu, Rie, Maki, Yuji, Sagami, Hiroshi, Koyama, Tanetoshi
Format: Article
Language:English
Subjects:
2-Cyclohexenylethyl diphosphate
Bacillus stearothermophilus
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
Cyclohexylideneethyl diphosphate
Farnesyl diphosphate synthase
Fundamental and applied biological sciences. Psychology
Methods. Procedures. Technologies
Substrate specificity
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Summary:We investigated the substrate specificity of farnesyl diphosphate (FPP) synthase derived from Bacillus stearothermophilus and porcine liver by examining the reactivities of two cyclic substrate homologs, cyclohexylideneethyl diphosphate and cyclohexenylethyl diphosphate. Reaction of geranyl diphosphate with 2-cyclohexenylethyl diphosphate using bacterial or porcine liver FPP synthase produced ( S)-geranylcyclohexylideneethyl diphosphate, with relative yields of 13.6% for the bacterial enzyme and 42.2% for the porcine liver enzyme. Reaction of cyclohexylideneethyl diphosphate with isopentenyl diphosphate produced 10-cyclohexyliden-3,7-dimethyldeca-2,6-dien-1-ol as a double condensation product, with relative yields of 23.1% (bacterial enzyme) and 3.0% (porcine liver enzyme). Reaction of cyclohexylideneethyl diphosphate with 2-cyclohexenylethyl diphosphate using bacterial enzyme produced (cyclohexylideneethyl)-cyclohexylideneethyl diphosphate (0.8% yield).
ISSN:1381-1177
1873-3158
DOI:10.1016/j.molcatb.2009.05.002