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Green Enzymatic Strategies for the Preparation of Chemically and Pharmaceutically Important Enantiomeric Compounds

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Green Chemistry".

Deadline for manuscript submissions: closed (1 November 2023) | Viewed by 1180

Special Issue Editors


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Guest Editor
Enzymatic Synthesis Group, Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary
Interests: stereochemistry; bioatalysis; asymmetric synthesis; green (sustainable) enzymatic chemistry

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Guest Editor
Bioorganic Chemistry Group, Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, Budapest, Hungary
Interests: biocatalysis; stereoselective synthesis; immobilization of biocatalysts; flow chemistry and biocatalysis; enzyme mechanisms
Special Issues, Collections and Topics in MDPI journals

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Guest Editor
Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Hungary
Interests: hydroxyquinolines; 8-quinolinols; 4-Hydroxyquinoline-2-carboxylic acid (KYNA); bioactive compounds; neuroprotection; antiproliferative activity
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

There is a continually growing demand for enantiomerically pure products. Enantiomers of chemically and pharmaceutically interesting compounds and their key intermediates or building blocks for their synthesis can be obtained either from transformations of enantiomerically pure compounds called “chiral pool”, involving mostly natural compounds, such as amino acids, carbohydrates, terpenes and steroids, or from asymmetric syntheses (which often involve the use of expensive enantiomerically pure auxiliary reagents). The enzymatic methods for asymmetric synthesis exploiting the biocatalysts’ inherent enantiomer or enantiotope selectivity represent clear advantages. Enzyme-based catalysis is starting to challenge traditional synthetic methods of producing optically active compounds.

By using enzymes in reactions, the previous reactions under harsh conditions can be coaxed to proceed faster under mild conditions (lower temperatures and pressures; neutral pH), with fewer work-up steps and a higher yield, all of which results in the improvement in the reaction’s efficiency and saves energy.

In the last two decades, many efficient enzymatic strategies (kinetic, dynamic kinetic, sequential kinetic resolution of racemates; desymmetrization of meso and prochiral substrates) and new techniques have been published for the synthesis of enantiopure products. Although a great number of innovative enzymatic routes that involve either using a nature-friendly solvent (water, green organic solvent, or supercritical solvent) or refrain from using any added solvent, based on the principle the best solvent is no solvent, have been published. Sustainable mechanoenzymatic kinetic resolution of several racemic compounds, with the use of ball milling, has also been described.

To attain sustainable enzymatic green strategies that allow the large-scale production of high-value enantiomeric pharmaceuticals, agrochemicals and flavor compounds, one must identify the most suitable biocatalyst (a biocatalyst that can be produced from readily available resources and is biodegradable, nonhazardous and nontoxic) and the best nature-friendly reaction conditions. In the frame of design approaches, the physicochemical (e.g. immobilization of the enzyme) and reaction engineering methods (e.g. the use of different acyl donors or nucleophiles, solvents, etc.) will remain important in future developments. Biocatalyst, reactor engineering and investigation of the cascade systems are to be highlighted.

In the present Special Issue, innovative and sustainable green enzymatic strategies for the preparation of chemically or/and pharmaceutically important enantiopure compounds will be analyzed.

Prof. Dr. Enikő Forró
Prof. Dr. László Poppe
Prof. Dr. István Szatmári
Guest Editors

Manuscript Submission Information

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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. Molecules is an international peer-reviewed open access semimonthly 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

  • green biocatalyst
  • sustainable enzymatic strategy
  • valuable enantiopure compound
  • environmentally-friendly conditions
  • biodegradable and non-toxic solvent
  • solvent-free system
  • supercritical fluid
  • green work-up
  • green analytical technique

Published Papers (1 paper)

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Review

14 pages, 2290 KiB  
Review
Lipase-Catalyzed Strategies for the Preparation of Enantiomeric THIQ and THβC Derivatives: Green Aspects
by György Orsy and Enikő Forró
Molecules 2023, 28(17), 6362; https://doi.org/10.3390/molecules28176362 - 30 Aug 2023
Cited by 1 | Viewed by 891
Abstract
This report reviews the most important lipase-catalyzed strategies for the preparation of pharmaceutically and chemically important tetrahydroisoquinoline and tetrahydro-β-carboline enantiomers through O-acylation of the primary hydroxy group, N-acylation of the secondary amino group, and COOEt hydrolysis of the [...] Read more.
This report reviews the most important lipase-catalyzed strategies for the preparation of pharmaceutically and chemically important tetrahydroisoquinoline and tetrahydro-β-carboline enantiomers through O-acylation of the primary hydroxy group, N-acylation of the secondary amino group, and COOEt hydrolysis of the corresponding racemic compounds with simple molecular structure, which have been reported during the last decade. A brief introduction describes the importance and synthesis of tetrahydroisoquinoline and tetrahydro-β-carboline derivatives, and it formulates the objectives of this compilation. The strategies are presented in chronological order, classified according to function of the reaction type, as kinetic and dynamic kinetic resolutions, in the main text. These reactions result in the desired products with excellent ee values. The pharmacological importance of the products together with their synthesis is given in the main text. The enzymatic hydrolysis of the hydrochloride salts as racemates of the starting amino carboxylic esters furnished the desired enantiomeric amino carboxylic acids quantitatively. The enzymatic reactions, performed in tBuOMe or H2O as usable solvents, and the transformations carried out in a continuous-flow system, indicate clear advantages, including atom economy, reproducibility, safer solvents, short reaction time, rapid heating and compression vs. shaker reactions. These features are highlighted in the main text. Full article
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