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Related Concept Videos

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

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 surface of...
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...
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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.
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

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...

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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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A stereoselective cobalt-containing nitrile hydratase

M S Payne1, S Wu, R D Fallon

  • 1Central Research and Development and Agricultural Products Department, DuPont, Wilmington, Delaware 19880-0328, USA.

Biochemistry
|May 6, 1997
PubMed
Summary

This study characterizes a cobalt-containing nitrile hydratase from Pseudomonas putida, revealing its stereoselective catalysis and structural gene sequencing. The enzyme exhibits high activity and stability, suggesting a novel metalloenzyme class with cobalt-thiolate ligation.

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Area of Science:

  • Biochemistry
  • Enzymology
  • Structural Biology

Background:

  • Nitrile hydratases are enzymes that catalyze nitrile hydration.
  • Cobalt-containing nitrile hydratases represent a distinct class with unique catalytic properties.
  • Understanding enzyme structure-activity relationships is crucial for biocatalysis.

Purpose of the Study:

  • To purify and characterize nitrile hydratase from Pseudomonas putida NRRL-18668.
  • To investigate the stereoselectivity of the enzyme's nitrile hydration activity.
  • To determine the metal coordination and gene sequence of the enzyme.

Main Methods:

  • Enzyme purification and characterization.
  • Spectroscopic analysis (UV-Vis, CD, EPR) for metal ion characterization.
  • Gene cloning, sequencing, and homology analysis.

Main Results:

  • The purified enzyme exhibits high stereoselectivity, favoring the (S)-enantiomer of 2-(4'-chlorophenyl)-3-methylbutyronitrile.
  • Spectroscopic data indicate the presence of a low-spin Co3+ ion coordinated by thiolates, suggesting a novel metalloenzyme class.
  • Gene sequencing revealed homology to other nitrile hydratases, with conserved cysteine residues potentially involved in metal coordination.

Conclusions:

  • The Pseudomonas putida nitrile hydratase is a cobalt-dependent enzyme with significant stereoselectivity.
  • The enzyme's structural and metal coordination properties suggest it belongs to a newly identified class of metalloenzymes.
  • This characterization provides insights into the diversity of nitrile hydratases and their potential applications in biocatalysis.