title: Efficient asymmetric organocatalytic formation of erythrose and threose under aqueous conditions.
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.
authors.affiliation: Department of Chemistry, University of York, Heslington, York, UK YO10 5DD.
authors.forename: Laurence
authors.initials: L
authors.lastname: Burroughs
authors.forename: Matthew E
authors.initials: ME
authors.lastname: Vale
authors.forename: James A R
authors.initials: JA
authors.lastname: Gilks
authors.forename: Henrietta
authors.initials: H
authors.lastname: Forintos
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Hayes
authors.forename: Paul A
authors.initials: PA
authors.lastname: Clarke
mesh_terms: D000409:Alanine / Q000737:chemistry; D002384:Catalysis; D007930:Leucine / Q000737:chemistry; D056692:Prebiotics; D011392:Proline / Q000737:chemistry; D013237:Stereoisomerism; D013780:Tetroses / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
chemical_list: D056692:Prebiotics; D013780:Tetroses; D014867:Water; D011392:Proline; D007930:Leucine; D000409:Alanine; C073321:erythrose