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Revisiting the HO

Dinh Hieu Truong1,2, Thi Huong Lan Nguyen3, Duy Quang Dao1,2

  • 1Institute of Research and Development, Duy Tan University, Da Nang 550000, Vietnam.

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|June 9, 2023
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Summary
This summary is machine-generated.

The oxidation of L-proline (Pro) by hydroxyl radical (HO●) primarily occurs at the beta- and gamma-carbons. Transition metal ions like iron and copper can enhance Pro oxidation, particularly in low oxidation states.

Keywords:
DFTantioxidantcopper complexesiron complexesl-prolinepro-oxidant

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Area of Science:

  • Computational Chemistry
  • Biochemistry
  • Environmental Chemistry

Background:

  • L-proline (Pro) is an amino acid susceptible to oxidation.
  • Hydroxyl radical (HO●) is a key reactive oxygen species involved in oxidative processes.
  • Transition metal ions (Fe, Cu) can influence radical reactions and biological oxidation.

Purpose of the Study:

  • To investigate the oxidation mechanism of L-proline by hydroxyl radical.
  • To explore the impact of transition metal ions (Fe, Cu) on L-proline oxidation.
  • To determine the reactivity and complexation behavior of L-proline with metal ions.

Main Methods:

  • Density Functional Theory (DFT) calculations at the M05-2X/6-311++G(3df,3pd)//M05-2X/6-311++G(d,p) level.
  • Analysis of hydrogen atom transfer (HAT) pathways and reaction rate constants.
  • Modeling of L-proline complexation with Fe and Cu ions.

Main Results:

  • HO●-initiated oxidation of Pro occurs mainly at beta- and gamma-carbons (44.6% and 39.5% branching ratios).
  • The overall rate constant for Pro oxidation by HO● is 6.04 × 10^8 M^-1 s^-1.
  • Pro forms stable complexes with Fe and Cu ions via the carboxylate group.
  • Low oxidation state metal complexes (Fe(II)-Pro, Cu(I)-Pro) significantly enhance Pro oxidation risk.

Conclusions:

  • The study elucidates the primary sites and kinetics of L-proline oxidation by hydroxyl radicals.
  • Complexation with transition metals, especially in low oxidation states, increases L-proline's susceptibility to oxidation.
  • Findings are relevant to understanding oxidative stress mechanisms and metal-catalyzed degradation processes.