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Related Concept Videos

IR and UV–Vis Spectroscopy of Carboxylic Acids01:28

IR and UV–Vis Spectroscopy of Carboxylic Acids

6.0K
In IR spectroscopy of carboxylic acids, the C=O bond shows a characteristic band between 1710 and 1760 cm⁻¹, and the O–H bond exhibits a broad band between 2500 and 3300 cm⁻¹.
However, the stretching absorptions for the C=O bond vary depending on the structure of carboxylic acids. The C=O bond of the free carboxylic acids shows a higher stretching frequency, 1760 cm−1, while H-bonded carboxylic acids (dimers) exhibit stretching absorptions at a lower frequency,...
6.0K
NMR and Mass Spectroscopy of Carboxylic Acids01:30

NMR and Mass Spectroscopy of Carboxylic Acids

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In ¹H NMR spectroscopy, acidic protons (–COOH) of carboxylic acids are highly deshielded and absorb far downfield, at around 9–12 ppm. The chemical shift value depends on the concentration and solvent used.
While α protons of carboxylic acids absorb at 2–2.5 ppm, β protons absorb further upfield.
Carboxylic acids are easily identified by dissolving them in deuterium oxide, which results in a rapid exchange of the acidic protons with deuterium. This leads to the...
5.4K
Spectroscopy of Carboxylic Acid Derivatives01:26

Spectroscopy of Carboxylic Acid Derivatives

3.1K
Infrared spectroscopy is primarily used to determine the types of bonds and functional groups. In carboxylic acid derivatives, a typical carbonyl bond absorption is observed around 1650–1850 cm−1. For esters, the absorption is recorded at around 1740 cm−1, while acid halides show the absorption at about 1800 cm−1. Another acid derivative, the acid anhydrides, exhibit two carbonyl absorption around 1760 cm−1 and 1820 cm−1, arising from the symmetrical and...
3.1K
Reactions of Carboxylic Acids: Introduction01:41

Reactions of Carboxylic Acids: Introduction

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Carboxylic acids possess an acidic –COOH functional group. The acidity can be attributed to the resonance stabilization of their conjugate base, wherein the negative charge is delocalized over both oxygen atoms.
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Organic Compounds03:02

Organic Compounds

58.0K
All living things are formed mostly of carbon compounds called organic compounds. The category of organic compounds includes both natural and synthetic compounds that contain carbon. Although a single, precise definition has yet to be identified by the chemistry community, most agree that a defining trait of organic molecules is the presence of carbon as the principal element, bonded to hydrogen and other carbon atoms. However, some carbon-containing compounds such as carbonates, cyanides, and...
58.0K
Physical Properties of Carboxylic Acids01:31

Physical Properties of Carboxylic Acids

6.4K
Carboxylic acids with lower molecular weight exhibit a sharp and unpleasant odor. They also have higher boiling and melting points than analogous compounds, such as aldehydes, ketones, and alcohols.
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Qualitative Identification of Carboxylic Acids, Boronic Acids, and Amines Using Cruciform Fluorophores
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Covalent Probe Finds Carboxylic Acid.

Alexander Jones1, Xiaoyun Zhang1, Xiaoguang Lei2

  • 1Synthetic and Functional Biomolecules Center, Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, Peking University, Beijing 100871, China; Department of Chemical Biology, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China.

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Summary

Researchers developed a novel method for selectively targeting carboxylic acids in proteins using isoxazolium salts. This breakthrough enables new protein ligation techniques and the creation of covalent drugs.

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Area of Science:

  • Chemical Biology
  • Organic Chemistry
  • Proteomics

Background:

  • Selective modification of proteins is crucial for chemical biology research and drug development.
  • Targeting specific amino acid residues, such as carboxylic acids, presents a challenge in chemical proteomics.

Purpose of the Study:

  • To introduce a new chemical strategy for the selective covalent modification of binding site carboxylic acids within the proteome.
  • To demonstrate the utility of isoxazolium salts as effective warheads for targeting these specific functional groups.

Main Methods:

  • Development of isoxazolium salts as reactive chemical probes.
  • Application of these probes for selective covalent labeling of carboxylic acids in a proteomic context.
  • Characterization of the reaction mechanism and selectivity.

Main Results:

  • Demonstrated selective covalent targeting of binding site carboxylic acids.
  • Established isoxazolium salts as a versatile chemical tool for protein modification.
  • Validated the strategy for potential applications in protein ligation and drug discovery.

Conclusions:

  • The isoxazolium salt strategy offers a powerful new approach for selective covalent targeting of carboxylic acids.
  • This method has significant implications for advancing protein ligation technologies and developing novel covalent therapeutics.