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Molecules 2017, 22(10), 1591; doi:10.3390/molecules22101591

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

1
Politecnico di Milano, Dipartimento di Chimica, Materiali, Ingegneria Chimica, Via Mancinelli 7, I-20131 Milano, Italy
2
Istituto di Chimica del Riconoscimento Molecolare—CNR, Via M. Bianco 9, I-20131 Milano, Italy
Authors are listed in alphabetical order. M. C. is the principal author of the publication.
*
Author to whom correspondence should be addressed.
Received: 24 July 2017 / Revised: 12 September 2017 / Accepted: 21 September 2017 / Published: 22 September 2017
(This article belongs to the Collection Recent Advances in Flavors and Fragrances)
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Abstract

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. View Full-Text
Keywords: pheromone; stereoselectivity; biocatalysis; ene-reductase; alcohol dehydrogenase pheromone; stereoselectivity; biocatalysis; ene-reductase; alcohol dehydrogenase
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Brenna, E.; Crotti, M.; Gatti, F.G.; Monti, D.; Parmeggiani, F.; Pugliese, A. One-Pot Multi-Enzymatic Synthesis of the Four Stereoisomers of 4-Methylheptan-3-ol. Molecules 2017, 22, 1591.

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