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Asymmetric organocatalytic formation of protected and unprotected tetroses under potentially prebiotic conditions

2011; Royal Society of Chemistry; Volume: 10; Issue: 8 Linguagem: Inglês

10.1039/c1ob06798b

1477-0539

Laurence Burroughs, Paul A. Clarke, Henrietta Forintos, James A. R. Gilks, Christopher J. Hayes, Matthew E. Vale, W. H. Wade, Myriam Zbytniewski,

Enzyme Catalysis and Immobilization

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.