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Related Concept Videos

Amino acids03:42

Amino acids

88.9K
Amino acids are the monomers that comprise proteins. Each amino acid has the same fundamental structure, which consists of a central carbon atom, or the alpha (α) carbon, bonded to an amino group (NH2), a carboxyl group (COOH), and to a hydrogen atom. Every amino acid also has another atom or group of atoms bonded to the central atom known as the R group. There are 20 common amino acids present in proteins, each with a different R group. Variation in the amino acid sequence is responsible...
88.9K
NMR and Mass Spectroscopy of Carboxylic Acids01:30

NMR and Mass Spectroscopy of Carboxylic Acids

3.9K
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...
3.9K
What are Proteins?01:55

What are Proteins?

208.7K
Overview
208.7K
Acidity and Basicity of Carboxylic Acid Derivatives01:25

Acidity and Basicity of Carboxylic Acid Derivatives

3.4K
Carboxylic acids are the strongest among organic acids, as they readily lose the hydroxyl proton to form a resonance-stabilized carboxylate ion. In comparison, the acid derivatives lack acidic hydrogens directly attached to a functional group. In these compounds, the acidic nature arises from their ability to lose α hydrogens, making them weakly acidic.
The relative acidic strength of the derivatives can be explained based on the extent of resonance stabilization of the conjugate base. The...
3.4K
Basicity of Aliphatic Amines01:21

Basicity of Aliphatic Amines

5.9K
Amines can behave as Brønsted–Lowry bases by accepting a proton from the acid to form corresponding conjugate acids. Due to a lone pair of nonbonding electrons, aliphatic amines can also act as Lewis bases by forming a covalent bond with an electrophile.
To measure the basicity of amines, two conventions are generally used. The first defines Kb as the basicity constant for the deprotonation reaction of water by the amine, as presented in Figure 1. Conventionally, lower Kb indicates...
5.9K
Acidity of Carboxylic Acids01:21

Acidity of Carboxylic Acids

7.0K
Carboxylic acids are the strongest organic acids. However, their acidic strength is much less than mineral acids like HCl. Carboxylic acids ionize in water and readily lose the hydroxyl proton to form a resonance-stabilized carboxylate ion.
7.0K

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Determination of the Gas-phase Acidities of Oligopeptides
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Determination of the Gas-phase Acidities of Oligopeptides

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Pinpointing Acidic Residues in Proteins.

Weimin Xuan1, Jun-An Ma2

  • 1Frontiers Science Center for Synthetic Biology, Tianjin Key Laboratory of Function and Application of Biological Macromolecular Structures, School of Life Sciences, Tianjin University, Tianjin, 300072, China.

Chemmedchem
|February 2, 2024
PubMed
Summary

Targeting acidic residues like aspartic acid (Asp) and glutamic acid (Glu) in proteins is crucial for controlling protein function and drug development. Recent advances enable precise manipulation of these sites using novel chemical tools.

Keywords:
aspartatecovalent druggenetic code expansionglutamatenoncanonical amino acidphotolabeling

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Area of Science:

  • Protein engineering and chemical biology
  • Small molecule drug discovery

Background:

  • Precise control over protein function is essential for biological mechanisms and therapeutic interventions.
  • Acidic residues, specifically aspartic acid (Asp) and glutamic acid (Glu), are prevalent and functionally significant in proteins.
  • The potential of targeting acidic residues remains largely untapped.

Purpose of the Study:

  • To highlight recent advancements in manipulating acidic residues within proteins.
  • To introduce novel chemical strategies for targeting Asp and Glu residues.
  • To discuss challenges and future directions in the field.

Main Methods:

  • Review of electrophiles reactive towards carboxylic acids.
  • Exploration of light-induced reactions targeting carboxylic acids.
  • Introduction of genetically encoded noncanonical amino acids for protein modification.

Main Results:

  • Demonstration of chemical tools enabling targeted modification of Asp and Glu residues.
  • Highlighting the utility of electrophilic reactions and photochemistry for carboxylic acid modification.
  • Showcasing the application of noncanonical amino acids for site-specific protein engineering.

Conclusions:

  • Significant progress has been made in developing methods to manipulate acidic residues.
  • Electrophiles, photochemistry, and noncanonical amino acids offer powerful approaches for protein control.
  • Further research is needed to address existing challenges and fully exploit the potential of targeting acidic residues.