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

Ronald Breslow, Mindy S. Levine

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

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.

Original languageEnglish
Pages (from-to)1809-1812
Number of pages4
JournalTetrahedron Letters
Volume47
Issue number11
DOIs
StatePublished - 13 Mar 2006
Externally publishedYes

Keywords

  • Amino acids
  • Chirality
  • Murchison carbonaceous chondritic meteorites
  • Origin of optical activity
  • Transaminations

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