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Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
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Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
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Wolff–Kishner reduction involves converting aldehydes and ketones to alkanes using hydrazine and a base. The reaction converts a carbonyl group to a methylene group. The method was independently discovered by N. Kishner in 1911 and L. Wolff in 1912. The reduction is carried out in high-boiling solvents such as ethylene glycol and diethylene glycol because heat is required to deprotonate the N–H proton in one of the reaction steps.

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Reengineered carbonyl reductase for reducing methyl-substituted cyclohexanones.

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Protein Engineering, Design & Selection : PEDS
|January 29, 2013
PubMed
Summary

Candida parapsilosis carbonyl reductase (CPCR2) engineering improved its ability to process bulky substrates. The L119M variant shows significantly enhanced activity on 2-methyl cyclohexanone, broadening CPCR2

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Area of Science:

  • Biocatalysis and Enzyme Engineering
  • Organic Chemistry
  • Protein Engineering

Background:

  • Candida parapsilosis carbonyl reductase (CPCR2) is a known biocatalyst for producing optically pure alcohols from ketones.
  • CPCR2 exhibits a broad substrate spectrum but poorly accepts sterically hindered prochiral ketones like 2-methyl cyclohexanone.

Purpose of the Study:

  • To investigate and engineer the substrate specificity of CPCR2.
  • To enhance the enzyme's activity towards poorly accepted substrates, specifically 2-methyl cyclohexanone.

Main Methods:

  • Site-saturation mutagenesis was performed on five key amino acid positions (55, 92, 118, 119, and 262) of CPCR2.
  • Enzyme libraries were screened using both well-accepted and poorly accepted ketone substrates.
  • Molecular docking was used to rationalize the observed changes in substrate specificity.

Main Results:

  • Mutagenesis at positions 92, 118, and 262 did not yield beneficial variants.
  • Positions 55 and 119 influenced enzyme activity.
  • The L119M variant demonstrated a 7-fold increase in activity towards 2-methyl cyclohexanone and improved activity on other substituted cyclohexanones.

Conclusions:

  • The L119M substitution is a promising strategy for broadening the substrate spectrum of CPCR2.
  • Enzyme engineering can enhance the biocatalytic utility of CPCR2 for sterically demanding substrates.
  • This study provides foundational insights for redesigning CPCR2 for improved performance with diverse ketone substrates.