Related Experiment Video
Updated: Jan 18, 2026
10:12
Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
13.5K
Interfacial π-π Stacking Interaction Promotes H2-Driven Enzymatic Asymmetric Reduction
Wei Lan1, Jingru Yang1, Jiabao Wei1
1Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Zhejiang Key Laboratory of Advanced Catalysis and Adsorption Materials, Institute of Physical Chemistry, Zhejiang Normal University, Jinhua, 321004, China.
Angewandte Chemie (International Ed. in English)
|January 16, 2026
Summary
This study introduces a Pickering emulsion microreactor for efficient NADH regeneration using H2. The system achieves high selectivity and over 2000 cycles, advancing sustainable chemoenzymatic reductions.
Area of Science:
- Biocatalysis and Green Chemistry
- Materials Science and Engineering
- Chemical Engineering
Background:
- In situ hydrogen (H2)-driven nicotinamide adenine dinucleotide (phosphate) (NAD(P)H) regeneration is crucial for sustainable chemoenzymatic reductions.
- Challenges include low selectivity in NAD(P)H formation and mutual deactivation between chemical catalysts and enzymes, hindering efficiency.
Purpose of the Study:
- To develop a novel oil-in-water Pickering emulsion microreactor for highly selective and efficient in situ NADH regeneration.
- To construct a chemoenzymatic microreactor for asymmetric reductive resolution using the developed NADH regeneration system.
Main Methods:
- Utilized an oil-in-water Pickering emulsion microreactor with interfacial π-π stacking for directional H* transfer.
- Integrated the NADH regeneration system with horse liver alcohol dehydrogenase (HLADH) for asymmetric reductive resolution.
- Employed H2 as the reductant for the chemoenzymatic process.
Main Results:
- Achieved >99% selectivity in NADH regeneration.
- Demonstrated >99% enantiomeric excess (ee) for the chiral alcohol product, (S)-(-)-2-phenyl-1-propanol.
- Sustained over 2000 NADH regeneration cycles, a record for H2-driven systems.
Conclusions:
- The Pickering emulsion microreactor effectively separates catalysts, mitigating deactivation and enhancing NADH regeneration efficiency.
- This approach offers a promising strategy for developing sustainable and efficient chemoenzymatic microreactors for chiral chemical production.
![Protein Film Infrared Electrochemistry Demonstrated for Study of H2 Oxidation by a [NiFe] Hydrogenase](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F55858.jpg&w=3840&q=50)
Related Concept Videos
02:17Reduction 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...
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
01:18Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism
2.6K
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...
2.6K
02:13Reduction of Alkenes: Catalytic Hydrogenation
13.9K
Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
13.9K
01:19Acid 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...
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
02:24Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
8.9K
Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
8.9K
02:23Alcohols from Carbonyl Compounds: Reduction
12.1K
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...
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...
12.1K