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Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

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If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
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Multiple Halogenation of Methyl Ketones: Haloform Reaction01:28

Multiple Halogenation of Methyl Ketones: Haloform Reaction

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A method involving the transformation of methyl ketones to carboxylic acids using excess base and halogen is called the haloform reaction. It begins with the deprotonation of α hydrogen to form an enolate ion which reacts with the electrophilic halogen to give an α-halo ketone. The step continues until all the α protons are substituted to form a trihalomethyl ketone. The resulting molecule is unstable, and in the presence of a hydroxide base, it readily undergoes nucleophilic...
2.2K
Alkyl Halides02:45

Alkyl Halides

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Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
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Halogenation of Alkenes02:46

Halogenation of Alkenes

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Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
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Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

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By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic...
3.1K
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

12.5K
An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
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A Toolkit to Enable Hydrocarbon Conversion in Aqueous Environments
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Computational library design for increasing haloalkane dehalogenase stability.

Robert J Floor1, Hein J Wijma, Dana I Colpa

  • 1Department of Biochemistry, Groningen Biomolecular Sciences and Biotechnology Institute, University of Groningen, Nijenborgh 4, 9747 AG Groningen (The Netherlands).

Chembiochem : a European Journal of Chemical Biology
|July 1, 2014
PubMed
Summary
This summary is machine-generated.

Computational design stabilized the haloalkane dehalogenase LinB enzyme. This resulted in a mutant with significantly increased thermostability and longer half-life, enabling higher concentration reactions.

Keywords:
co-solventscomputational designdehalogenasesdirected evolutionthermostabilityvirtual screening

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Area of Science:

  • Biocatalysis
  • Protein Engineering
  • Computational Biology

Background:

  • Haloalkane dehalogenases (HDLs) are crucial enzymes for bioremediation.
  • Improving the stability of enzymes like LinB is essential for industrial applications.
  • Computational methods offer a powerful approach to enzyme engineering.

Purpose of the Study:

  • To computationally design and experimentally validate stabilizing mutations for the haloalkane dehalogenase LinB.
  • To investigate the impact of mutations in flexible regions on protein thermostability.
  • To enhance the operational performance of LinB for industrial biocatalysis.

Main Methods:

  • Utilized a computational design framework including energy calculations and molecular dynamics simulations.
  • Employed disulfide bond design and rational inspection of mutant protein structures.
  • Screened mutant libraries to identify and validate stabilizing mutations.

Main Results:

  • Identified seventeen point mutations and one disulfide bond enhancing LinB thermostability.
  • Mutations in flexible regions showed a greater stabilizing effect.
  • A combined twelve mutations yielded a LinB mutant with a 23°C higher melting temperature and over 200-fold increased half-life at 60°C.

Conclusions:

  • Computational design is effective for enhancing enzyme thermostability.
  • Targeting flexible regions can lead to significant improvements in enzyme stability.
  • Engineered LinB variants exhibit improved performance in co-solvent environments, broadening their industrial applicability.