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Isomerization of trans-3-methylglutaconic acid.

Dylan E Jones1, J David Ricker2, Laina M Geary2

  • 1Department of Biochemistry and Molecular Biology University of Nevada Reno Reno Nevada USA.

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|March 17, 2021
PubMed
Summary

3-Methylglutaconic (3MGC) aciduria involves isomers. The trans-3MGC acid isomerizes to cis-3MGC acid in vitro, suggesting both forms occur in patients with this metabolic disorder.

Keywords:
3‐methylglutaconic aciduriaNMR spectroscopycis:trans isomerizationgas chromatography‐mass spectrometryinborn errors of metabolismmitochondria

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Area of Science:

  • Biochemistry
  • Metabolic Disorders
  • Organic Chemistry

Background:

  • 3-Methylglutaconic (3MGC) aciduria is a common phenotype in various inborn errors of metabolism.
  • It can be primary (leucine pathway enzyme deficiencies) or secondary (mitochondrial energy production defects).
  • The precursor to 3MGC acid is trans-3MGC CoA, an intermediate in leucine catabolism.

Purpose of the Study:

  • To investigate the isomeric forms of 3-Methylglutaconic acid.
  • To understand the potential for isomerization between trans-3MGC acid and cis-3MGC acid.
  • To determine if these isomers are relevant to 3MGC aciduria.

Main Methods:

  • Gas chromatography-mass spectrometry (GC-MS) analysis of trans-3MGC acid.
  • Proton nuclear magnetic resonance (1H-NMR) spectroscopy.
  • Incubation studies at varying temperatures and conditions.
  • Molecular modeling studies.

Main Results:

  • GC-MS analysis of trans-3MGC acid revealed a mixture of cis and trans isomers.
  • 1H-NMR confirmed trans-3MGC acid isomerizes to cis-3MGC acid under specific incubation conditions, including those mimicking sample derivatization and at 37°C.
  • Molecular modeling indicated cis-3MGC acid is energetically more stable than trans-3MGC acid.
  • Both diastereomers are proposed to occur in urine samples from patients with 3MGC aciduria.

Conclusions:

  • Trans-3MGC acid can isomerize to cis-3MGC acid in vitro.
  • This isomerization is likely facilitated by a mechanism involving pi electron delocalization and resonance structures.
  • The findings support the presence of both cis and trans isomers in patients with 3-Methylglutaconic aciduria.