Efficient asymmetric organocatalytic formation of erythrose and threose under aqueous conditions

Laurence Burroughs, Matthew E. Vale, James A. R. Gilks, Henrietta Forintos, Christopher J. Hayes, Paul A. Clarke

Research output: Contribution to journalArticlepeer-review

Abstract

Esters of proteinogenic amino acids efficiently catalyse the formation of erythrose and threose under aqueous conditions in the highest yields and enantioselectivities yet reported. Remarkably while esters of (L)-proline yield (L)-carbohydrates, esters of (L)-leucine and (L)-alanine generate (D)-carbohydrates, offering the potential to account for the prebiotic link between natural (L)-amino acids and natural (D)-sugars.

Original languageEnglish
Pages (from-to)4776-4778
Number of pages3
JournalChemical Communications
Volume46
Issue number26
DOIs
Publication statusPublished - 14 Jul 2010

Keywords

  • ACID CATALYZED NEOGENESIS
  • ALDOL REACTIONS
  • 2-STEP SYNTHESIS
  • WATER
  • HOMOCHIRALITY
  • ORIGIN
  • MEDIA

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