title: Asymmetric organocatalytic formation of protected and unprotected tetroses under potentially prebiotic conditions.
abstract: Esters of proteinogenic amino acids efficiently catalyse the formation of erythrose and threose under potentially prebiotic conditions in the highest yields and enantioselectivities yet reported. Remarkably while esters of (L)-proline yield (L)-tetroses, esters of (L)-leucine, (L)-alanine and (L)-valine generate (D)-tetroses, offering the potential to account for the link between natural (L)-amino acids and natural (D)-sugars. The effect of pH and NaCl on the yields and enantioselectivities was also investigated and was shown to be significant, with the optimal enantioselectivities occurring at pH 7.
authors.affiliation: Department of Chemistry, University of York, Heslington, York, North Yorks, UK YO10 5DD.
authors.forename: Laurence
authors.initials: L
authors.lastname: Burroughs
authors.forename: Paul A
authors.initials: PA
authors.lastname: Clarke
authors.forename: Henrietta
authors.initials: H
authors.lastname: Forintos
authors.forename: James A R
authors.initials: JA
authors.lastname: Gilks
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Hayes
authors.forename: Matthew E
authors.initials: ME
authors.lastname: Vale
authors.forename: William
authors.initials: W
authors.lastname: Wade
authors.forename: Myriam
authors.initials: M
authors.lastname: Zbytniewski
mesh_terms: D000596:Amino Acids / Q000737:chemistry; D002384:Catalysis; D006863:Hydrogen-Ion Concentration; D015394:Molecular Structure; D013237:Stereoisomerism; D013780:Tetroses / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D013780:Tetroses