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Sugars to Acids via Thioesters: A Computational Study.

Jeremy Kua1, Jonathan D Karin1

  • 1Department of Chemistry & Biochemistry, University of San Diego, San Diego, CA 92110, USA.

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|August 28, 2025
PubMed
Summary
This summary is machine-generated.

Sugars can transform into carboxylic acids without enzymes via a thiol-aldehyde reaction. While thermodynamically favorable, reaction rates are limited by water or hydrogen sulfide elimination, suggesting alpha di-carbonyls are more efficient catalysts.

Keywords:
origins of lifeprebiotic chemistryproto-metabolismthioester

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Area of Science:

  • Biochemistry
  • Astrochemistry
  • Organic Chemistry

Background:

  • Core metabolic cycles like the TCA cycle rely on carboxylic acids and thioesters.
  • The formose reaction produces sugars, a potential precursor for prebiotic chemistry.
  • Enzymatic pathways are typically required for metabolic conversions.

Purpose of the Study:

  • To investigate the non-enzymatic conversion of sugars to carboxylic acids.
  • To evaluate the thermodynamics and kinetics of proposed prebiotic metabolic pathways.
  • To identify favorable reaction mechanisms and intermediates for early life chemistry.

Main Methods:

  • Thermodynamic calculations of reaction pathways.
  • Kinetic analysis to identify rate-limiting steps.
  • Modeling of thiol-aldehyde addition and thioester formation/hydrolysis.

Main Results:

  • A proposed non-enzymatic pathway converts sugars to carboxylic acids via thioester intermediates.
  • The reaction mechanism is thermodynamically favorable.
  • Kinetic bottlenecks were identified, particularly in dehydration steps (H2O or H2S elimination).
  • Alpha di-carbonyl compounds show greater feasibility as they bypass rate-limiting elimination steps.

Conclusions:

  • Non-enzymatic synthesis of carboxylic acids from sugars is plausible under prebiotic conditions.
  • Thioester intermediates are key to this conversion.
  • Reaction kinetics, specifically dehydration steps, present challenges, favoring alternative reactants like alpha di-carbonyls for efficient catalysis.