Prebiotic formation of `energy-rich' thioesters from glyceraldehyde and N-acetylcysteine

Details Prebiotic formation of `energy-rich' thioesters from glyceraldehyde and N-acetylcysteine Prebiotic formation of `energy-rich' thioesters from glyceraldehyde and N-acetylcysteine

Mar 1984

adsabs.harvard.edu/cgi-bin/nph-data_query?bibcode=1984orli...15...17w&link_type=abstract

Origins of Life and Evolution of the Biosphere, Volume 15, Issue 1, pp.17-27

Physics

12

Scientific paper

The ‘energy-rich’ thioester, N-acetyl-S-lactoylcysteine, is formed from low concentrations of glyceraldehyde and N-acetylcysteine under anaerobic conditions at ambient temperature in aqueous solutions of sodium phosphate (pH 7.0). Reactions with 2 mM glyceraldehyde, 2 mM N-acetylcysteine, and 500 mM sodium phosphate (pH 7.0) convert about 0.3%/day of the glyceraldehyde to lactoyl thioester. The formation of lactoyl thioester in similar reactions with 500 mM imidazole hydrochloride (pH 7.0) is supported by the thiol-dependence of lactate formation, which is 3-fold greater in the presence of thiol (0.11%/day) than in the absence of thiol (0.04%/day). The formation of lactoyl thioester is thought to proceed by the phosphate (or imidazole)-catalyzed dehydration of glyceraldehyde to give pyruvaldehyde, which adds to the thiol to form a hemithioacetal that rearranges to the thioester. A limited amount of a second thioester, N-acetyl-S-glyceroyl-cysteine, is also formed at the beginning of these reactions. The significance of these reactions to the origin of life is discussed.

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