Next Article in Journal
Catalysts—Looking Back and Peering Ahead
Next Article in Special Issue
Old Yellow Enzyme-Catalysed Asymmetric Hydrogenation: Linking Family Roots with Improved Catalysis
Previous Article in Journal
Mechanistic Analysis of Water Oxidation Catalyst cis-[Ru(bpy)2(H2O)2]2+: Effect of Dimerization
Previous Article in Special Issue
N-acetylglucosamine 2-Epimerase from Pedobacter heparinus: First Experimental Evidence of a Deprotonation/Reprotonation Mechanism
Article Menu
Issue 2 (February) cover image

Export Article

Open AccessFeature PaperCommunication
Catalysts 2017, 7(2), 37; doi:10.3390/catal7020037

Stereoselective Chemoenzymatic Synthesis of Optically Active Aryl-Substituted Oxygen-Containing Heterocycles

1
Dipartimento di Farmacia-Scienze del Farmaco, Università degli Studi di Bari «Aldo Moro», Consorzio C.I.N.M.P.I.S., Via E. Orabona 4, I-70125 Bari, Italy
2
Department of Biosciences, Biotechnologies and Biopharmaceutics, University of Bari, Via E. Orabona 4, I-70125 Bari, Italy
3
Consorzio C.I.R.C.C. Via Celso Ulpiani 27, I-70126 Bari, Italy
4
Dipartimento di Scienze e Tecnologie Biologiche ed Ambientali, Università del Salento, Prov.le Lecce-Monteroni, I-73100 Lecce, Italy
5
CNR ICCOM, Dipartimento di Chimica, Università di Bari, Via E. Orabona 4, I-70125 Bari, Italy
Dedicated to Professor Luigino Troisi on the occasion of his retirement.
*
Authors to whom correspondence should be addressed.
Academic Editors: Jose M. Palomo and Cesar Mateo
Received: 22 December 2016 / Revised: 16 January 2017 / Accepted: 17 January 2017 / Published: 25 January 2017
(This article belongs to the Special Issue Asymmetric and Selective Biocatalysis)
View Full-Text   |   Download PDF [1316 KB, uploaded 25 January 2017]   |  

Abstract

A two-step stereoselective chemoenzymatic synthesis of optically active α-aryl-substituted oxygen heterocycles was developed, exploiting a whole-cell mediated asymmetric reduction of α-, β-, and γ-chloroalkyl arylketones followed by a stereospecific cyclization of the corresponding chlorohydrins into the target heterocycles. Among the various whole cells screened (baker’s yeast, Kluyveromyces marxianus CBS 6556, Saccharomyces cerevisiae CBS 7336, Lactobacillus reuteri DSM 20016), baker’s yeast was the one providing the best yields and the highest enantiomeric ratios (up to 95:5 er) in the bioreduction of the above ketones. The obtained optically active chlorohydrins could be almost quantitatively cyclized in a basic medium into the corresponding α-aryl-substituted cyclic ethers without any erosion of their enantiomeric integrity. In this respect, valuable, chiral non-racemic functionalized oxygen containing heterocycles (e.g., (S)-styrene oxide, (S)-2-phenyloxetane, (S)-2-phenyltetrahydrofuran), amenable to be further elaborated on, can be smoothly and successfully generated from their prochiral precursors. View Full-Text
Keywords: whole cell biocatalyst; baker’s yeast; enantioselective bioreduction; oxiranes; oxetanes; tetrahydrofurans; halohydrins; chloroketones; oxygen-containing heterocycles; chemoenzymatic synthesis whole cell biocatalyst; baker’s yeast; enantioselective bioreduction; oxiranes; oxetanes; tetrahydrofurans; halohydrins; chloroketones; oxygen-containing heterocycles; chemoenzymatic synthesis
Figures

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).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Vitale, P.; Digeo, A.; Perna, F.M.; Agrimi, G.; Salomone, A.; Scilimati, A.; Cardellicchio, C.; Capriati, V. Stereoselective Chemoenzymatic Synthesis of Optically Active Aryl-Substituted Oxygen-Containing Heterocycles. Catalysts 2017, 7, 37.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Catalysts EISSN 2073-4344 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top