Tryptophan analogues form adducts by cooperative reaction with aldehydes and alcohols or with aldehydes alone: possible role in ethanol toxicity.

@article{Austin1992TryptophanAF,
  title={Tryptophan analogues form adducts by cooperative reaction with aldehydes and alcohols or with aldehydes alone: possible role in ethanol toxicity.},
  author={J E Austin and H Fraenkel-conrat},
  journal={Proceedings of the National Academy of Sciences of the United States of America},
  year={1992},
  volume={89 18},
  pages={8439-42}
}
Previous work showed that the exocyclic amino groups of nucleic acid components react quickly at ambient temperature with acetaldehyde and ethanol to yield mixed acetals [R-NH-CH(CH3)-O-C2H5]. We now find that the same type of reaction occurs readily with the nitrogen of 3-substituted indoles (e.g., indole-3-acetic acid and N-acetyltryptophan), analogues of the amino acid tryptophan. In contrast, unsubstituted indole reacts very rapidly at the carbon in ring position 2 or 3 with acetaldehyde to… CONTINUE READING