Elsevier

Tetrahedron Letters

Volume 47, Issue 11, 13 March 2006, Pages 1809-1812
Tetrahedron Letters

Partial transfer of enantioselective chiralities from α-methylated amino acids, known to be of meteoritic origin, into normal amino acids

https://doi.org/10.1016/j.tetlet.2006.01.018Get rights and content

Abstract

There is overwhelming evidence that meteorites bring α-methylated amino acids to earth with some l(S) enantiomeric excess. How does that get transferred into normal biological molecules? In this brief account, we show that an α-methylated amino acid, d(R)-α-methylvaline, can react with pyruvate and phenylpyruvate salts in dry mixtures to form alanine and phenylalanine with l enantiomeric excesses, under sensible prebiotic conditions. Thus the meteoritic l(S) excesses of this compound would produce excess d-alanine and d-phenylalanine, which are found in some organisms.

Section snippets

Acknowledgments

We thank Dr. Jason Chruma and Dr. Jiaming Yan for some preliminary work and helpful suggestions, and the NSF and NIH for financial support.

References and notes (20)

  • S. Pizzarello et al.

    Geochim. Cosmochim. Acta

    (2000)
  • S. Pizzarello et al.

    Geochim. Cosmochim. Acta

    (2003)
  • M.H. Engel et al.

    Nature

    (1982)
  • S. Pizzarello et al.

    Geochim. Cosmochim. Acta

    (2004)
  • J.R. Cronin et al.
  • S.A. Sheeley et al.

    Analyst

    (2005)
  • J.R. Cronin et al.

    Science

    (1997)
  • C. Girard et al.

    Angew. Chem., Int. Ed.

    (1998)
    K. Soai et al.

    Acc. Chem. Res.

    (2000)
  • J. Podlech

    Cell. Mol. Life Sci.

    (2001)
  • J.L. Bada et al.

    Biosystems

    (1987)
There are more references available in the full text version of this article.

Cited by (14)

  • Ronald C.D. Breslow (1931–2017): A career in review

    2021, Bioorganic Chemistry
    Citation Excerpt :

    Combined with a pyridoxamine/pyridoxal small molecule cofactor (vide supra),[330] these systems were able to dramatically accelerate the transamination of ketoacids to amino acids. As a natural continuation of his research in transamination reactions, Breslow developed a prebiotically relevant transamination reaction,[547] in which an excess of a homochiral, C-α-methyl amino acid (α-methyl valine) found on meteorites was combined with an achiral ketoacid, 3-phenylpropanoic acid, to generate phenylalanine with up to 9.5% ee. The proposed reaction mechanism, which occurs via a decarboxylative transamination reaction (Fig. 44), relies on the chiral C-α-methyl amino acid 68a to act both as a source of nitrogen and as a chiral proton source, via its zwitterionic, ammonium-containing state.

View all citing articles on Scopus
View full text