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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Main Authors:	Elisabetta Brenna, Michele Crotti, Francesco G. Gatti, Daniela Monti, Fabio Parmeggiani, Andrea Pugliese
Format:	Article
Language:	English
Published:	MDPI AG 2017-09-01
Series:	Molecules
Subjects:	pheromone stereoselectivity biocatalysis ene-reductase alcohol dehydrogenase
Online Access:	https://www.mdpi.com/1420-3049/22/10/1591

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spelling	doaj-54b0116206ba44e386568c2b056e8a5a2020-11-25T00:51:50ZengMDPI AGMolecules1420-30492017-09-012210159110.3390/molecules22101591molecules22101591One-Pot Multi-Enzymatic Synthesis of the Four Stereoisomers of 4-Methylheptan-3-olElisabetta Brenna0Michele Crotti1Francesco G. Gatti2Daniela Monti3Fabio Parmeggiani4Andrea Pugliese5Politecnico di Milano, Dipartimento di Chimica, Materiali, Ingegneria Chimica, Via Mancinelli 7, I-20131 Milano, ItalyPolitecnico di Milano, Dipartimento di Chimica, Materiali, Ingegneria Chimica, Via Mancinelli 7, I-20131 Milano, ItalyPolitecnico di Milano, Dipartimento di Chimica, Materiali, Ingegneria Chimica, Via Mancinelli 7, I-20131 Milano, ItalyIstituto di Chimica del Riconoscimento Molecolare—CNR, Via M. Bianco 9, I-20131 Milano, ItalyPolitecnico di Milano, Dipartimento di Chimica, Materiali, Ingegneria Chimica, Via Mancinelli 7, I-20131 Milano, ItalyPolitecnico di Milano, Dipartimento di Chimica, Materiali, Ingegneria Chimica, Via Mancinelli 7, I-20131 Milano, ItalyThe 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.https://www.mdpi.com/1420-3049/22/10/1591pheromonestereoselectivitybiocatalysisene-reductasealcohol dehydrogenase
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Elisabetta Brenna Michele Crotti Francesco G. Gatti Daniela Monti Fabio Parmeggiani Andrea Pugliese
spellingShingle	Elisabetta Brenna Michele Crotti Francesco G. Gatti Daniela Monti Fabio Parmeggiani Andrea Pugliese One-Pot Multi-Enzymatic Synthesis of the Four Stereoisomers of 4-Methylheptan-3-ol Molecules pheromone stereoselectivity biocatalysis ene-reductase alcohol dehydrogenase
author_facet	Elisabetta Brenna Michele Crotti Francesco G. Gatti Daniela Monti Fabio Parmeggiani Andrea Pugliese
author_sort	Elisabetta Brenna
title	One-Pot Multi-Enzymatic Synthesis of the Four Stereoisomers of 4-Methylheptan-3-ol
title_short	One-Pot Multi-Enzymatic Synthesis of the Four Stereoisomers of 4-Methylheptan-3-ol
title_full	One-Pot Multi-Enzymatic Synthesis of the Four Stereoisomers of 4-Methylheptan-3-ol
title_fullStr	One-Pot Multi-Enzymatic Synthesis of the Four Stereoisomers of 4-Methylheptan-3-ol
title_full_unstemmed	One-Pot Multi-Enzymatic Synthesis of the Four Stereoisomers of 4-Methylheptan-3-ol
title_sort	one-pot multi-enzymatic synthesis of the four stereoisomers of 4-methylheptan-3-ol
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2017-09-01
description	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.
topic	pheromone stereoselectivity biocatalysis ene-reductase alcohol dehydrogenase
url	https://www.mdpi.com/1420-3049/22/10/1591
work_keys_str_mv	AT elisabettabrenna onepotmultienzymaticsynthesisofthefourstereoisomersof4methylheptan3ol AT michelecrotti onepotmultienzymaticsynthesisofthefourstereoisomersof4methylheptan3ol AT francescoggatti onepotmultienzymaticsynthesisofthefourstereoisomersof4methylheptan3ol AT danielamonti onepotmultienzymaticsynthesisofthefourstereoisomersof4methylheptan3ol AT fabioparmeggiani onepotmultienzymaticsynthesisofthefourstereoisomersof4methylheptan3ol AT andreapugliese onepotmultienzymaticsynthesisofthefourstereoisomersof4methylheptan3ol
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One-Pot Multi-Enzymatic Synthesis of the Four Stereoisomers of 4-Methylheptan-3-ol

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