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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.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
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Phase I biotransformation reductive reactions are chemical processes that modify drugs by introducing or revealing polar functional groups via reduction. Enzymes called reductases catalyze these reactions, playing a pivotal role in drug metabolism by transforming lipophilic drugs into more polar, water-soluble metabolites for easy excretion. An essential type of reductive reaction is the carbonyl group reduction, where aldehydes and ketones are reduced to alcohols. An example is the...
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Preparation of Amines: Reduction of Amides and Nitriles01:13

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Nitriles can be reduced to primary amines using reducing agents like lithium aluminum hydride or catalytic hydrogenation. The reduction introduces an amino group with an extra carbon in the skeleton. Nitriles are formed from the reaction between alkyl halides and sodium cyanide through the SN2 mechanism. Primary alkyl halides are the preferred substrates to prepare nitriles.
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Nitriles to Amines: LiAlH4 Reduction00:55

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Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
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Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

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Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
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Alcohols from Carbonyl Compounds: Reduction02:23

Alcohols from Carbonyl Compounds: Reduction

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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...
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Methods to Identify the NMR Resonances of the 13C-Dimethyl N-terminal Amine on Reductively Methylated Proteins
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Installing Reduction Responsiveness into Biomolecules by Introducing Nitroaryl Groups.

Sayuri L Higashi1,2, Yuki Shintani3, Masato Ikeda1,3,4,5

  • 1United Graduate School of Drug Discovery and Medical Information Sciences, Gifu University, 1-1 Yanagido, Gifu, 501-1193, Japan.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|May 13, 2022
PubMed
Summary
This summary is machine-generated.

Researchers review the design of reduction-responsive biomolecules, like peptides and nucleic acids, using nitroaryl groups. These molecules offer new ways to monitor and control biological systems, especially those involving redox changes.

Keywords:
biomoleculesfoldingnitroaryl groupreductionself-assemblystimuli-responsiveness

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Area of Science:

  • Biochemistry
  • Molecular Biology
  • Chemical Biology

Background:

  • Stimuli-responsive biomolecules are valuable tools for biological research.
  • Redox stimuli are prevalent in biological systems, and their imbalance is associated with diseases.
  • Nitroaryl groups can be incorporated into biomolecules to create responsiveness.

Purpose of the Study:

  • To review the molecular design of reduction-responsive biomolecules.
  • To highlight the use of nitroaryl groups, particularly 4-nitrobenzene motifs, in creating these responsive biomolecules.
  • To discuss applications in monitoring and modulating biological systems.

Main Methods:

  • Review of existing literature on stimuli-responsive biomolecules.
  • Focus on the synthesis and design principles of incorporating nitroaryl groups into peptides, nucleic acids, and saccharides.
  • Analysis of the reduction-responsive mechanisms conferred by these modifications.

Main Results:

  • Nitroaryl groups, especially 4-nitrobenzene, enable the creation of biomolecules that respond to reduction stimuli.
  • These modified biomolecules (peptides, nucleic acids, saccharides) can be designed for specific biological applications.
  • The introduction of nitroaryl groups allows for controlled modulation of biological processes.

Conclusions:

  • Artificially synthesized reduction-responsive biomolecules are promising molecular tools.
  • The design strategies using nitroaryl groups provide a versatile platform for developing novel biological probes and therapeutics.
  • Further development in this area could lead to advanced methods for studying and treating redox-related diseases.