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Radical Halogenation: Stereochemistry01:33

Radical Halogenation: Stereochemistry

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Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:
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Radical Reactivity: Overview01:11

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Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
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Radical Halogenation: Thermodynamics01:34

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The thermodynamic favorability of a reaction is determined by the change in Gibbs free energy (ΔG). ΔG has two components- enthalpy (ΔH) and entropy (ΔS). The entropy component is negligible for alkane halogenation because the number of reactants and product molecules are equal. In this case, the ΔG is governed only by the enthalpy component. The most crucial factor that determines ΔH is the strength of the bonds. ΔH can be determined by comparing the energy...
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The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
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Radical Substitution: Halogenation of Alkanes and Alkyl Substituents01:27

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In the presence of heat or light, alkanes react with molecular halogens to form alkyl halides by a substitution reaction called radical halogenation. This reaction has three steps: initiation, propagation, and termination, as seen in the radical chlorination of methane to produce methyl chloride.
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Reactions at the Benzylic Position: Halogenation01:11

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Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
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RadH: A Versatile Halogenase for Integration into Synthetic Pathways.

Binuraj R K Menon1, Eileen Brandenburger1, Humera H Sharif1

  • 1School of Chemistry & Manchester Institute of Biotechnology, The University of Manchester, 131 Princess Street, Manchester, M1 7DN, UK.

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Summary

Fungal halogenase RadH regioselectively halogenates bioactive compounds. Evolving RadH via high-throughput screening and combining genes created a novel chlorinated coumarin in E. coli.

Keywords:
biocatalysisdirected evolutionenzyme mechanismshalogenasespathway engineering

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Area of Science:

  • Biochemistry
  • Enzymology
  • Synthetic Biology

Background:

  • Flavin-dependent halogenases are crucial biocatalysts for synthesizing halogenated molecules.
  • These enzymes offer improved biological activity or serve as intermediates in chemical synthesis.
  • Fungal halogenases, like RadH, present unique regioselectivity for specific molecular scaffolds.

Purpose of the Study:

  • To explore the regioselective halogenation capabilities of the fungal halogenase RadH on diverse bioactive aromatic scaffolds.
  • To elucidate the catalytic residues and mechanism of fungal halogenases through site-directed mutagenesis.
  • To engineer an improved RadH variant using high-throughput screening and construct a novel biosynthetic pathway for a non-natural product.

Main Methods:

  • Regioselective halogenation of aromatic scaffolds using fungal halogenase RadH.
  • Site-directed mutagenesis of RadH to identify key catalytic residues and understand its mechanism.
  • Development of a high-throughput fluorescence screen for enzyme evolution.
  • Construction of a synthetic pathway in E. coli by combining genes from fungi, bacteria, and plants.

Main Results:

  • Demonstrated successful regioselective halogenation of various bioactive aromatic compounds by RadH.
  • Identified critical catalytic residues within RadH, offering mechanistic insights into fungal halogenases.
  • Evolved a RadH mutant with enhanced properties through high-throughput screening.
  • Successfully generated a novel chlorinated coumarin product in E. coli by assembling a multi-organism biosynthetic pathway.

Conclusions:

  • Fungal halogenase RadH is a versatile tool for regioselective halogenation of bioactive molecules.
  • Enzyme engineering via high-throughput screening can significantly improve halogenase properties.
  • Combinatorial assembly of biosynthetic genes enables the creation of novel non-natural products.
  • This work expands the toolkit for biocatalytic halogenation and synthetic biology applications.