Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

3.4K
Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
3.4K
Esters to Alcohols: Hydride Reductions01:17

Esters to Alcohols: Hydride Reductions

4.6K
Esters are reduced to primary alcohols when treated with a strong reducing agent like lithium aluminum hydride. The reaction requires two equivalents of the reducing agent and proceeds via an aldehyde intermediate.
Lithium aluminum hydride is a source of hydride ions and functions as a nucleophile. The mechanism proceeds in three steps. Firstly, the nucleophilic hydride ion attacks the carbonyl carbon of the ester to form a tetrahedral intermediate. Subsequently, the carbonyl group re-forms,...
4.6K
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

11.2K
Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
11.2K
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

4.1K
Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...
4.1K
Acid Halides to Alcohols: LiAlH4 Reduction01:19

Acid Halides to Alcohols: LiAlH4 Reduction

3.8K
Acid halides are reduced to alcohols in the presence of a strong reducing agent like lithium aluminum hydride.
The mechanism proceeds in three steps. First, the nucleophilic hydride ion attacks the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs as a leaving group, generating an aldehyde. A second nucleophilic attack by the hydride yields an alkoxide ion, which, upon protonation, gives a primary alcohol as...
3.8K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.8K
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...
3.8K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Unlocking a Nitrosuccinate Lyase for Decarboxylative Enzymatic Hydronitration.

Angewandte Chemie (International ed. in English)·2026
Same author

Computational enzyme design by catalytic motif scaffolding.

Nature·2025
Same author

Mild hydrolysis of chemically stable valerolactams by a biocatalytic ATP-dependent system fueled by metaphosphate.

Green chemistry : an international journal and green chemistry resource : GC·2024
Same author

Redox Out of the Box: Catalytic Versatility Across NAD(P)H-Dependent Oxidoreductases.

Angewandte Chemie (International ed. in English)·2023
Same author

Stereodivergent Biocatalytic Formal Reduction of α-Angelica Lactone to (R)- and (S)-γ-Valerolactone in a One-Pot Cascade.

Chembiochem : a European journal of chemical biology·2023
Same author

Enzymatic strategies for asymmetric synthesis.

RSC chemical biology·2021
Same journal

Direct air capture technologies: innovations, integration, and pathways to scale.

Chemical Society reviews·2026
Same journal

Fluorescent merocyanines: from fundamental properties to applications as molecular probes, in bioimaging and as emissive dye aggregates.

Chemical Society reviews·2026
Same journal

Direct impure water electrolysis at industrial scale.

Chemical Society reviews·2026
Same journal

Catalytic valorization of polyolefins: from catalysts and processes to reactors.

Chemical Society reviews·2026
Same journal

Designing stable π-radicals.

Chemical Society reviews·2026
Same journal

Antibacterial drug discovery: challenges and preclinical promises from synthetic small molecules.

Chemical Society reviews·2026
See all related articles

Related Experiment Video

Updated: Jan 4, 2026

Hydrogen Production and Utilization in a Membrane Reactor
10:00

Hydrogen Production and Utilization in a Membrane Reactor

Published on: March 10, 2023

3.1K

Enzymatic self-sufficient hydride transfer processes.

Erika Tassano1, Mélanie Hall1

  • 1Department of Chemistry, University of Graz, Heinrichstrasse 28, 8010, Graz, Austria. melanie.hall@uni-graz.at.

Chemical Society Reviews
|November 2, 2019
PubMed
Summary
This summary is machine-generated.

Biocatalysis utilizes nicotinamide cofactors for efficient hydride transfer, creating sustainable synthetic routes with high atom and hydride economy. This review examines strategies for maximizing cofactor turnover and minimizing by-products in enzymatic reactions.

More Related Videos

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
10:52

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

Published on: July 27, 2022

3.2K
Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions
10:21

Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions

Published on: October 5, 2019

8.8K

Related Experiment Videos

Last Updated: Jan 4, 2026

Hydrogen Production and Utilization in a Membrane Reactor
10:00

Hydrogen Production and Utilization in a Membrane Reactor

Published on: March 10, 2023

3.1K
Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex
10:52

Line Shape Analysis of Dynamic NMR Spectra for Characterizing Coordination Sphere Rearrangements at a Chiral Rhenium Polyhydride Complex

Published on: July 27, 2022

3.2K
Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions
10:21

Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions

Published on: October 5, 2019

8.8K

Area of Science:

  • Biocatalysis
  • Organic Chemistry
  • Enzymology

Background:

  • Nicotinamide cofactors are essential for self-sufficient hydride transfer in biocatalysis.
  • These cofactors act as hydride shuttles, connecting enzymatic redox events and ensuring redox neutrality.
  • Existing systems often achieve high hydride and atom economy.

Purpose of the Study:

  • To analyze and classify strategies for self-sufficient hydride transfer in biocatalysis.
  • To evaluate the efficiency of these systems based on hydride economy and nicotinamide cofactor turnover.
  • To critically assess current systems and identify areas for improvement.

Main Methods:

  • Review and classification of reported self-sufficient hydride transfer processes.
  • Focus on efficiency metrics, specifically hydride economy.
  • Measurement of nicotinamide cofactor turnover number.

Main Results:

  • Creative systems enable one-pot, one-step functionalization of diverse molecules.
  • These systems prevent by-product formation, enhancing sustainability.
  • Efficiency is strongly correlated with hydride economy and cofactor turnover.

Conclusions:

  • Self-sufficient hydride transfer systems offer significant advantages in biocatalysis.
  • Maximizing nicotinamide cofactor turnover is key to improving efficiency.
  • Further research is needed to optimize existing strategies and develop new ones.