Mercaptopropionaldehyde from homocysteine: implications for Alzheimer's disease

J Alzheimers Dis. 2007 Nov;12(3):241-3. doi: 10.3233/jad-2007-12305.

Abstract

There has been evidence for a causal relationship between homocysteine and Alzheimer's disease for several years but the mechanism is unclear. In vivo, some homocysteine is converted to the thiolactone. This report describes a novel reaction between homocysteine thiolactone and dehydroascorbic acid in which the homocysteine thiolactone is converted to 3-mercaptopropionaldehyde. This product is shown to react with proteins causing their precipitation (probably by cross-linking). The two reactions are extremely facile and appear to be physiologically compatible suggesting a mechanism by which homocysteine may promote the deposition of proteins in nerve cells as amyloid plaques and fibrillary tangles.

MeSH terms

  • 3-Mercaptopropionic Acid / chemistry
  • 3-Mercaptopropionic Acid / metabolism*
  • Aldehydes / chemistry
  • Aldehydes / metabolism*
  • Alzheimer Disease / metabolism*
  • Alzheimer Disease / pathology
  • Amyloid beta-Protein Precursor / metabolism
  • Chemical Precipitation
  • Homocysteine / analogs & derivatives*
  • Homocysteine / chemistry
  • Homocysteine / metabolism
  • Humans
  • Neurofibrillary Tangles / metabolism
  • Neurofibrillary Tangles / pathology
  • Plaque, Amyloid / metabolism
  • Plaque, Amyloid / pathology

Substances

  • Aldehydes
  • Amyloid beta-Protein Precursor
  • Homocysteine
  • 3-Mercaptopropionic Acid
  • homocysteine thiolactone