One-Pot Multi-Enzymatic Synthesis of the Four Stereoisomers of 4-Methylheptan-3-ol

The use of pheromones in the integrated pest management of insects is currently considered a sustainable and environmentally benign alternative to hazardous insecticides. 4-Methylheptan-3-ol is an interesting example of an insect pheromone, because its stereoisomers are active towards different spec...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2017-09, Vol.22 (10), p.1591
Main Authors: Brenna, Elisabetta, Crotti, Michele, Gatti, Francesco G, Monti, Daniela, Parmeggiani, Fabio, Pugliese, Andrea
Format: Article
Language:English
Subjects:
Agricultural practices
Agrochemicals
Alcohol dehydrogenase
Alcohol Dehydrogenase - metabolism
Alcohols
Animals
biocatalysis
Catalysis
ene-reductase
Environmental management
Enzymatic synthesis
Insecta - drug effects
Insecticides
Insecticides - chemical synthesis
Insecticides - chemistry
Insecticides - pharmacology
Integrated pest management
Pest control
pheromone
Pheromones
Pheromones - chemistry
Reductase
Stereoisomerism
Stereoisomers
stereoselectivity
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Summary:The use of pheromones in the integrated pest management of insects is currently considered a sustainable and environmentally benign alternative to hazardous insecticides. 4-Methylheptan-3-ol is an interesting example of an insect pheromone, because its stereoisomers are active towards different species. All four possible stereoisomers of this compound were prepared from 4-methylhept-4-en-3-one by a one-pot procedure in which the two stereogenic centres were created during two sequential reductions catalysed by an ene-reductase (ER) and an alcohol dehydrogenase (ADH), respectively.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules22101591