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Journal of Molecular Evolution

, Volume 18, Issue 5, pp 354–359 | Cite as

Formation of the thioester, N-acetyl, S-lactoylcysteine, by reaction of N-acetylcysteine with pyruvaldehyde in aqueous solution

  • Arthur L. Weber
Article

Summary

N-acetylcysteine reacts efficiently with pyruvaldehyde (methylglyoxal) in aqueous solution (pH 7.0) in the presence of a weak base, like imidazole or phosphate, to give the thioester, N-acetyl, S-lactoylcysteine. Reactions of 100 mM N-acetylcysteine with 14 mM, 24 mM and 41 mM pyruvaldehyde yield, respectively, 86%, 76% and 59% N-acetyl, S-lactoylcysteine based on pyruvaldehyde. The decrease in the percent yield at higher pyruvaldehyde concentrations suggests that during its formation the thioester is not only consumed by hydrolysis, but also by reaction with some substance in the pyruvaldehyde preparation. Indeed, purified N-acetyl, S-lactoylcysteine disappears much more rapidly in the presence of pyruvaldehyde than in its absence. Presumably, N-acetyl, S-lactoylcysteine synthesis occurs by rearrangement of the hemithioacetal of N-acetylcysteine and pyruvaldehyde. The significance of this pathway of thioester formation to molecular evolution is discussed.

Key words

Thioester Hemithioacetal Intramolecular rearrangement Molecular Evolution Prebiotic 

Abbreviations

Ac-Cys

N-acetylcysteine

Ac-Cys(Lac)

N-acetyl, S-lactoylcysteine

Im

imidazole

HPO4=

phosphate

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Copyright information

© Springer-Verlag 1982

Authors and Affiliations

  • Arthur L. Weber
    • 1
  1. 1.The Salk Institute for Biological StudiesSan DiegoUSA

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