Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
6.3
3.9
Journals
Catalysts
Special Issues
Biocatalytic Resolution of Chiral Molecules
share announcement

Biocatalytic Resolution of Chiral Molecules

A special issue of Catalysts (ISSN 2073-4344). This special issue belongs to the section "Biocatalysis".

Deadline for manuscript submissions: closed (31 December 2021) | Viewed by 5472

Special Issue Editors

Prof. Dr. Jaime Escalante

E-Mail Website
Guest Editor
Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Av. Universidad 1001, Chamilpa, Cuernavaca 62210, Mexico
Interests: asymmetric synthesis; synthesis and modification of peptides in catalysis and medicinal chemistry; biocatalysis; sustainable chemistry (green chemistry); synthesis of heterocyclic compounds
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Harald Gröger

E-Mail Website
Guest Editor
Industrial Organic Chemistry and Biotechnology, Faculty of Chemistry, Bielefeld University, Universitätsstrasse 25, 33615 Bielefeld, Germany
Interests: enzymatic processes; biocatalytic syntheses with whole cell-catalysts
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Eusebio Juaristi

E-Mail Website
Guest Editor
1. Department of Chemistry, Centro de Investigación y de Estudios Avanzados, Mexico City 07360, Mexico
2. El Colegio Nacional, Mexico City 06020, Mexico
Interests: stereochemistry; asymmetric organocatalysis; green chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Natural catalysts such as enzymes often outperform synthetic catalysts, both kinetically and in terms of selectivity (e.g., enantioselectivity). Biocatalysis can usually be carried out under mild conditions (e.g., ambient temperature and pressure, aqueous and organic solutions), and the catalysts used are generally biodegradable, biocompatible, and renewable, making these catalytic systems highly attractive for environmentally benign processes. A major application of enzymes, which has already gained industrial importance, are kinetic resolutions of racemic substrates. What makes enzymatic resolution attractive is the easy access to racemic substrates by means of many chemical methodologies in combination with the high efficiency and selectivity provided by the biocatalyst. In spite of the achievements in these fields, numerous challenges still exist.

This Special Issue will discuss recent developments in the preparation of enantiopure substances by means of enantioselective enzymatic resolutions and will include strategies that involve enzymatic catalysis in combination with chemical, photochemical, mechanochemical, and other types of non-traditional activation. A further focus of this special Issue will also be on dynamic kinetic resolution processes combining enzymatic resolutions with novel types of chemocatalytic or enzymatic racemization steps.

Prof. Dr. Jaime Escalante
Prof. Dr. Harald Gröger
Prof. Dr. Eusebio Juaristi
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Catalysts is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • acylation
  • alcohols
  • amines
  • dynamic kinetic resolution
  • esterases
  • fine chemicals
  • hydrolysis
  • kinetic resolution
  • lipases
  • organic reaction media
  • pharmaceutical products
  • proteases
  • β-amino acids
  • CaL-B

Published Papers (2 papers)

Download All Papers
Order results
Result details
Show export options expand_more Show export options expand_less
Select all
Export citation of selected articles as:

Research

18 pages, 976 KiB  
Article
Chemoenzymatic Stereoselective Synthesis of trans-Flavan-4-ols via Lipase-Catalyzed Kinetic Resolutions
by Martín Soto, Irene Sanz-Machín, Humberto Rodríguez-Solla and Vicente Gotor-Fernández
Catalysts 2021, 11(11), 1296; https://doi.org/10.3390/catal11111296 - 27 Oct 2021
Cited by 1 | Viewed by 2094
Abstract
Flavan-4-ols are a subclass of flavonoids that are present in complex molecules with application in the industrial sector as pigments, antioxidants, or antimitotics, among many others. The most traditional way to achieve their synthesis is from naturally abundant flavanones, asymmetric transfer hydrogenation reactions [...] Read more.
Flavan-4-ols are a subclass of flavonoids that are present in complex molecules with application in the industrial sector as pigments, antioxidants, or antimitotics, among many others. The most traditional way to achieve their synthesis is from naturally abundant flavanones, asymmetric transfer hydrogenation reactions or bioreduction being well known strategies, while their preparation from racemic flavan-4-ols has been less explored. In this article, we have focused on the synthesis of a series of trans-flavan-4-ols bearing different substitution patterns in the aromatic ring to explore later the potential of lipases as biocatalysts for stereoselective acylation reactions. Therefore, a series of flavanones have been chemically prepared, starting from the corresponding benzaldehydes by aldol condensation with 2′-hydroxyacetophenone in a strongly basic medium, and later transformed into the corresponding racemic trans-flavan-4-ols following a carbonyl reduction, Mitsunobu reaction, and ester deprotection sequence. A screening of lipases and optimization of the reaction conditions for the stereoselective acylation of racemic 2-phenylchroman-4-ol were performed before expanding the best reaction conditions to the kinetic resolution of other 2-arylchroman-4-ols. Interestingly, the combination of AK lipase from Pseudomonas fluorescens as enzyme and vinyl acetate as both acyl donor and solvent allowed the performance of highly asymmetric transformations (E > 200, 50–99% eeS and >99% eeP) under mild reaction conditions (30 °C and 250 rpm). Full article
(This article belongs to the Special Issue Biocatalytic Resolution of Chiral Molecules)
►▼ Show Figures

Graphical abstract

10 pages, 1088 KiB  
Article
Lipase-Catalyzed Kinetic Resolution of Alcohols as Intermediates for the Synthesis of Heart Rate Reducing Agent Ivabradine
by Anna Morandini, Arianna Rossetti and Alessandro Sacchetti
Catalysts 2021, 11(1), 53; https://doi.org/10.3390/catal11010053 - 01 Jan 2021
Cited by 1 | Viewed by 2635
Abstract
Ivabradine (Corlanor®), is a chiral benzocycloalkane currently employed and commercialized for the treatment of chronic stable angina pectoris and for the reduction in sinus tachycardia. The eutomer (S)-ivabradine is usually produced via chiral resolution of intermediates, by employing enantiopure [...] Read more.
Ivabradine (Corlanor®), is a chiral benzocycloalkane currently employed and commercialized for the treatment of chronic stable angina pectoris and for the reduction in sinus tachycardia. The eutomer (S)-ivabradine is usually produced via chiral resolution of intermediates, by employing enantiopure auxiliary molecules or through preparative chiral HPLC separations. Recently, more sustainable biocatalytic approaches have been reported in literature for the preparation of the chiral amine precursor. In this work, we report on a novel biocatalyzed pathway, via a resolution study of a key alcohol intermediate used as a precursor of the chiral amine. After screening several enzymatic reaction conditions, employing different lipases and esterases both for the esterification and hydrolysis reactions, the best result was achieved with Pseudomonas cepacia Lipase and the final product was obtained in up to 96:4 enantiomeric ratio (e.r.) of an ivabradine alcohol precursor. This enantiomer was then efficiently converted into the desired amine in a facile three step synthetic sequence. Full article
(This article belongs to the Special Issue Biocatalytic Resolution of Chiral Molecules)
►▼ Show Figures

Graphical abstract

Show export options expand_more Show export options expand_less
Select all
Export citation of selected articles as:
 
Displaying articles 1-2
Back to TopTop