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Related Concept Videos

Alcohols from Carbonyl Compounds: Reduction02:23

Alcohols from Carbonyl Compounds: Reduction

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.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
Preparation of Aldehydes and Ketones from Carboxylic Acid Derivatives01:18

Preparation of Aldehydes and Ketones from Carboxylic Acid Derivatives

Aldehydes are more reactive than carboxylic acids and hence, can get over-reduced to alcohol in the presence of strong reducing agents. Therefore, carboxylic acids are inefficient in preparing aldehydes using LAH.
Carboxylic acid derivatives like acid chlorides and esters are more easily reducible than the corresponding acids. The derivatives reduce in the presence of mild reducing agents to give aldehydes. Aldehydes can also be prepared by Rosenmund reduction, that is, the reduction of acid...
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes01:33

Preparation of Aldehydes and Ketones from Alcohols, Alkenes, and Alkynes

Aldehydes and ketones are prepared from alcohols, alkenes, and alkynes via different reaction pathways. Alcohols are the most commonly used substrates for synthesizing aldehydes and ketones. The conversion of alcohol to aldehyde, which involves the oxidation process, depends on the class of the alcohol used and the strength of the oxidizing agent. For instance, primary alcohol will form an aldehyde when treated with a weak oxidizing agent; however, it gets over-oxidized to a carboxylic acid in...
α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview

The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
Conversion of Alcohols to Alkyl Halides02:48

Conversion of Alcohols to Alkyl Halides

This lesson delves into the conversion of alcohols to corresponding alkyl halides and the mechanism of action for different reagents. Typically, the hydroxyl group is first protonated to convert it to a stable leaving group. Consequently, based on the starting alcohol, the mechanism undergoes either of the nucleophilic substitution routes, SN1 or SN2. Tertiary alkyl halides are made using the two-step SN1 mechanism that occurs via a carbocation intermediate, which is stabilized by...

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Updated: Jun 17, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
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Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine

Published on: February 16, 2018

Practical chiral alcohol manufacture using ketoreductases.

Gjalt W Huisman1, Jack Liang, Anke Krebber

  • 1Codexis Inc, 200 Penobscot Drive, Redwood City, CA 94063, USA. gjalt.huisman@codexis.com

Current Opinion in Chemical Biology
|January 15, 2010
PubMed
Summary

Ketoreductases are revolutionizing chiral alcohol synthesis, becoming the preferred biocatalyst over traditional methods. Advanced enzyme engineering and molecular biology enable tailor-made solutions for industrial demands.

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Separation of Aldehydes and Reactive Ketones from Mixtures Using a Bisulfite Extraction Protocol
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Separation of Aldehydes and Reactive Ketones from Mixtures Using a Bisulfite Extraction Protocol

Published on: April 2, 2018

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

Related Experiment Videos

Last Updated: Jun 17, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
09:14

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine

Published on: February 16, 2018

Separation of Aldehydes and Reactive Ketones from Mixtures Using a Bisulfite Extraction Protocol
09:08

Separation of Aldehydes and Reactive Ketones from Mixtures Using a Bisulfite Extraction Protocol

Published on: April 2, 2018

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
06:31

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

Area of Science:

  • Biocatalysis
  • Organic Synthesis
  • Enzyme Engineering

Background:

  • Ketoreductases (KREDs) have emerged as powerful biocatalysts for chiral alcohol synthesis.
  • Biocatalysis is increasingly favored over traditional chemical catalysts due to economic and environmental pressures.
  • Recent advancements in enzyme engineering have led to highly efficient and specific ketoreductases.

Purpose of the Study:

  • To review the recent revolution in ketoreductase applications for commercial chiral alcohol synthesis.
  • To highlight the shift towards biocatalysis as a preferred method in industrial ketone reduction.
  • To discuss enabling technologies driving biocatalysis adoption in chemical synthesis.

Main Methods:

  • High-throughput (HTP) screening of enzyme variants.
  • Modern molecular biology techniques for enzyme engineering.
  • Development of versatile biocatalytic platforms for industrial applications.

Main Results:

  • Ketoreductases are now the preferred catalysts for chiral alcohol synthesis, displacing chemical reagents and catalysts.
  • Tailor-made enzymes with enhanced properties are generated using advanced screening and engineering.
  • Biocatalysis is transitioning from a niche tool to a primary choice in industrial synthesis.

Conclusions:

  • Biocatalysis, particularly using ketoreductases, represents a significant advancement in chiral alcohol production.
  • Enzyme engineering and platform development are key drivers for the industrial success of biocatalysis.
  • The trend indicates a sustainable and efficient future for biocatalytic methods in chemical manufacturing.