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Related Concept Videos

Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

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Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
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In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
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Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.
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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
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Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
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Oxime Catalysis by Freezing.

Stijn M Agten1, Dennis P L Suylen1, Tilman M Hackeng1

  • 1Department of Biochemistry, Cardiovascular Research Institute Maastricht (CARIM), University Maastricht , Maastricht 6229 ER, The Netherlands.

Bioconjugate Chemistry
|December 10, 2015
PubMed
Summary
This summary is machine-generated.

Freezing accelerates chemical reactions, contrary to expectations. This study demonstrates that freezing enhances oxime ligation in water, enabling efficient protein modification under mild conditions.

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Area of Science:

  • Biochemistry
  • Chemical Biology
  • Physical Chemistry

Background:

  • Chemical reaction rates typically decrease with lower temperatures.
  • Oxime ligation is a bioorthogonal reaction used for modifying biomolecules.
  • Developing efficient ligation methods under aqueous, neutral pH conditions is crucial for bioconjugation.

Purpose of the Study:

  • To investigate the effect of freezing on oxime ligation rates in aqueous solution.
  • To optimize a freezing-based protocol for efficient protein ligation.
  • To apply the developed method for conjugating ligands to proteins.

Main Methods:

  • Systematic study of freezing methods and rates on peptide model systems for oxime ligation.
  • Application of the optimized protocol to a chemokine protein modified with an acetyl butyrate group.
  • Conjugation of an aminooxy-labeled ligand to the modified protein.

Main Results:

  • Oxime ligation reaction rate was significantly accelerated by freezing in water at neutral pH.
  • The freezing method and rate were optimized for efficient ligation.
  • Successful conjugation of ligands to a chemokine protein was achieved using the improved protocol.

Conclusions:

  • Freezing can accelerate specific chemical reactions, such as oxime ligation, under aqueous conditions.
  • The developed freezing-based protocol provides an efficient method for protein ligation at low concentrations and neutral pH.
  • This approach offers a valuable tool for bioconjugation and the introduction of functional ligands into proteins.