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