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Biocatalysis in Organic Synthesis

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

Deadline for manuscript submissions: closed (31 May 2019) | Viewed by 13352

Special Issue Editors


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Guest Editor
Departamento de Química Orgánica, Universidad de Sevilla, 41014 Sevilla, Spain
Interests: biocatalysis; catalytic reactions; sustainable chemistry; pharmaceutical synthesis
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Guest Editor
1. Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Córdoba, Argentina
2. Instituto de Investigaciones en Físico-Química de Córdoba (INFIQC), CONICET
Interests: stereoselective synthesis; biocatalysis; artificial enzymatic cascades; redox processes; organosulfur and organoselenium chemistry; multicomponent reactions

Special Issue Information

Dear Colleagues,

The preparation of valuable chiral compounds requires the development of more efficient methodologies, in which selectivity and atom economy of the processes become the ‘evolutionary pressure’. Biocatalysis, i.e., the use of purified enzymes, cell free extracts or whole cells, as catalyst in organic processes, offers several advantages for the synthesis of high-added value materials. Thus, biocatalysts generally display exquisite selectivities while using mild and eco-friendly reaction conditions. Enzymatic reactions are economically feasible. Biocatalysis often face some drawbacks that hampered their complete application in organic methodologies, including low substrates concentrations or the need of expensive cofactor molecules for different types of reactions. In the last few years, several efforts have been devoted to overcoming these bottlenecks, including the preparation of immobilized biocatalysts, medium engineering with the use of different non-conventional media for biocatalyzed reactions, the development of efficient cofactor recycling systems, and even designing cascade reactions. In this Special Issue, we shall focus in the recent advances in the application of effective biocatalytic procedures in organic chemistry.

Dr. Gonzalo de Gonzalo
Dr. Fabricio R. Bisogno
Guest Editors

Manuscript Submission Information

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Keywords

  • Asymmetric synthesis
  • Biocatalyzed processes
  • Stereoselectivity
  • Medium engineering
  • Immobilized biocatalysts
  • Dynamic enzymatic processes
  • Cofactor recycling
  • Enzymatic synthesis of APIs

Published Papers (3 papers)

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Research

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12 pages, 1407 KiB  
Article
Characterization of a New DyP-Peroxidase from the Alkaliphilic Cellulomonad, Cellulomonas bogoriensis
by Mohamed H. Habib, Henriëtte J. Rozeboom and Marco W. Fraaije
Molecules 2019, 24(7), 1208; https://doi.org/10.3390/molecules24071208 - 27 Mar 2019
Cited by 28 | Viewed by 4376
Abstract
DyP-type peroxidases are heme-containing enzymes that have received increasing attention over recent years with regards to their potential as biocatalysts. A novel DyP-type peroxidase (CboDyP) was discovered from the alkaliphilic cellulomonad, Cellulomonas bogoriensis, which could be overexpressed in Escherichia coli [...] Read more.
DyP-type peroxidases are heme-containing enzymes that have received increasing attention over recent years with regards to their potential as biocatalysts. A novel DyP-type peroxidase (CboDyP) was discovered from the alkaliphilic cellulomonad, Cellulomonas bogoriensis, which could be overexpressed in Escherichia coli. The biochemical characterization of the recombinant enzyme showed that it is a heme-containing enzyme capable to act as a peroxidase on several dyes. With the tested substrates, the enzyme is most active at acidic pH values and is quite tolerant towards solvents. The crystal structure of CboDyP was solved which revealed atomic details of the dimeric heme-containing enzyme. A peculiar feature of CboDyP is the presence of a glutamate in the active site which in most other DyPs is an aspartate, being part of the DyP-typifying sequence motif GXXDG. The E201D CboDyP mutant was prepared and analyzed which revealed that the mutant enzyme shows a significantly higher activity on several dyes when compared with the wild-type enzyme. Full article
(This article belongs to the Special Issue Biocatalysis in Organic Synthesis)
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10 pages, 2204 KiB  
Communication
Unusual Polycyclic Fused Product by Oxidative Enzymatic Dimerisation of 5-methylpyrogallol Catalysed by Horseradish Peroxidase/H2O2
by Hélène Bouges, Kevin Calabro, Olivier P. Thomas and Sylvain Antoniotti
Molecules 2018, 23(10), 2619; https://doi.org/10.3390/molecules23102619 - 12 Oct 2018
Cited by 6 | Viewed by 4835
Abstract
During investigations on the peroxidase-catalysed oxidation of polyhydroxylated monoaromatic substrates such as 5-methylpyrogallol, we observed a spectacular dimerisation proceeding by dearomatisation in contrast with most common reaction patterns involving phenolics oxidation and dimerization. A tetracyclic fused product featuring an unusual 2-oxatetracyclo [6.3.1.01,6 [...] Read more.
During investigations on the peroxidase-catalysed oxidation of polyhydroxylated monoaromatic substrates such as 5-methylpyrogallol, we observed a spectacular dimerisation proceeding by dearomatisation in contrast with most common reaction patterns involving phenolics oxidation and dimerization. A tetracyclic fused product featuring an unusual 2-oxatetracyclo [6.3.1.01,6.04,12] dodecan-3-one core was obtained and characterized by combined NMR techniques and high resolution mass spectroscopy (HRMS). This is an example of a spontaneous cascade triggered by a simple enzymatic reaction that could provide new options for biosynthetic hypothesis and a synthetic method to access this complex core in one operation. Full article
(This article belongs to the Special Issue Biocatalysis in Organic Synthesis)
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Review

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18 pages, 1497 KiB  
Review
The Versatile Applications of DES and Their Influence on Oxidoreductase-Mediated Transformations
by Fatima Zohra Ibn Majdoub Hassani, Saaid Amzazi and Iván Lavandera
Molecules 2019, 24(11), 2190; https://doi.org/10.3390/molecules24112190 - 11 Jun 2019
Cited by 29 | Viewed by 3297
Abstract
In the last decade, new types of solvents called deep eutectic solvents (DES) have been synthesized and commercialized. Among their main advantages, they can be eco-friendly and are easy to synthesize at different molar ratios depending on the desired solvent properties. This review [...] Read more.
In the last decade, new types of solvents called deep eutectic solvents (DES) have been synthesized and commercialized. Among their main advantages, they can be eco-friendly and are easy to synthesize at different molar ratios depending on the desired solvent properties. This review aims to show the different uses of DES in some relevant biocatalytic redox reactions. Here we analyze oxidoreductase-mediated transformations that are performed in the presence of DES and compare them with the ones that avoided those solvents. DES were found to present advantages such as the increase in the product yield and enantiomeric excess in many reactions. Full article
(This article belongs to the Special Issue Biocatalysis in Organic Synthesis)
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