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Related Concept Videos

Mass Spectrometry of Amines01:19

Mass Spectrometry of Amines

4.1K
In mass spectroscopy, amines undergo fragmentation to give parent ions with odd molecule weights. This observed mass spectrum follows the nitrogen rule: a molecule with an odd number of nitrogen atoms produces a parent ion with an odd molecular weight. The remaining fragments have an even mass.
Amines undergo fragmentation through α cleavage, producing nitrogen-containing cations—iminium ions—and alkyl radicals. Mass spectra of aromatic and cyclic aliphatic amines exhibit...
4.1K
Mass Spectrometry: Carboxylic Acid, Ester, and Amide Fragmentation01:01

Mass Spectrometry: Carboxylic Acid, Ester, and Amide Fragmentation

1.2K
The fragmentation patterns observed for compounds such as carboxylic acids, esters, and amides in the mass spectra include ⍺-cleavage and McLafferty rearrangement. Fragmentation by ⍺-cleavage preferentially occurs at the carbon-carbon bond at the ⍺-position next to the carboxylic group to generate a neutral radical and a cation. Long chain compounds with hydrogen at their γ-carbon undergo McLafferty rearrangement to give a radical cation and a neutral alkene.
For example,...
1.2K
Mass Spectrometry: Amine Fragmentation00:55

Mass Spectrometry: Amine Fragmentation

1.5K
Amines can be identified using mass spectroscopy based on their characteristic fragmentation patterns. The molecular ions of amines undergo fragmentation via ⍺-cleavage. The ⍺-cleavage of the carbon-carbon bonds in amines generates an alkyl radical and resonance-stabilized nitrogen-containing cation.
In amines, the number of nitrogen atoms affects the mass of the molecular ion, which is described by the nitrogen rule of mass spectrometry. This rule states that a compound containing...
1.5K
Structure of Amines01:19

Structure of Amines

2.5K
The hybridized nitrogen atom in amines possesses a lone pair of electrons and is bound to three substituents with a bond angle of around 108°, which is less than the tetrahedral angle of 109.5°. However, the C–N–H bond angle is slightly larger at 112°, with a carbon–nitrogen bond length of 147 pm. This carbon–nitrogen bond length of of amines is longer than the carbon–oxygen bond of alcohols (143 pm) but shorter than alkanes’...
2.5K
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

5.7K
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
5.7K
¹H NMR: Complex Splitting01:13

¹H NMR: Complex Splitting

1.3K
A proton M that is coupled to a proton X results in doublet signals for M. However, NMR-active nuclei can be simultaneously coupled to more than one nonequivalent nucleus. When M is coupled to a second proton A, such as in styrene oxide, each peak in the doublet is split into another doublet.
Splitting diagrams or splitting tree diagrams are routinely used to depict such complex couplings. While drawing splitting diagrams, the splitting with the larger coupling constant is usually applied...
1.3K

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Separation and Quantification of Isomeric Forms of Aminobutyric Acids.

Kamal Awad1, Akhilla Kumar2, Marian N Aziz3

  • 1Bone-Muscle Research Center, College of Nursing and Health Innovation, The University of Texas at Arlington, Arlington, TX, USA. kamal.awad@uta.edu.

Methods in Molecular Biology (Clifton, N.J.)
|June 11, 2025
PubMed
Summary

Mirror-image enantiomers, like L- and D-BAIBA, have different biological effects. A new method accurately distinguishes these amino acid isomers, crucial for analytical chemistry and pharmacology.

Keywords:
(R)-3-aminoisobutyric acid (D-BAIBA)LC-MS/MSγ-aminobutyric acid (GABA)

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Area of Science:

  • Analytical Chemistry
  • Biochemistry
  • Pharmacology

Background:

  • Biological actions of enantiomers can differ significantly.
  • L- and D-enantiomers of beta-aminoisobutyric acid (BAIBA) and alpha-aminoisobutyric acid (AABA) exhibit distinct biological interactions.
  • Similar physicochemical properties of enantiomers pose challenges for accurate quantification.

Purpose of the Study:

  • To develop a novel methodology for distinguishing and quantifying amino acid enantiomers.
  • To accurately identify isomers and enantiomers of aminobutyric acid.
  • To overcome limitations of conventional methods like LC-MS/MS in enantiomer separation.

Main Methods:

  • Introduction of a novel analytical methodology.
  • Application of advanced techniques for isomer and enantiomer identification.
  • Development of protocols to separate L- and D-isoforms of amino acids.

Main Results:

  • Successful development of a method to accurately identify and quantify amino acid enantiomers.
  • Overcoming the challenge of distinguishing enantiomers with similar properties.
  • Enabling the separation of L- and D-BAIBA, previously quantified together.

Conclusions:

  • The novel methodology significantly advances analytical chemistry, biochemistry, and pharmacology.
  • Accurate enantiomer quantification is essential for understanding distinct biological actions.
  • This work provides a foundation for future research in chiral compound analysis.