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Issue 8, 2012
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Asymmetric organocatalytic formation of protected and unprotected tetroses under potentially prebiotic conditions

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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.

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

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Supplementary files

Article information


Submitted
26 Oct 2011
Accepted
10 Nov 2011
First published
16 Nov 2011

Org. Biomol. Chem., 2012,10, 1565-1570
Article type
Paper

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

L. Burroughs, P. A. Clarke, H. Forintos, J. A. R. Gilks, C. J. Hayes, M. E. Vale, W. Wade and M. Zbytniewski, Org. Biomol. Chem., 2012, 10, 1565
DOI: 10.1039/C1OB06798B

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