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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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Publication details

The article was received on 26 Oct 2011, accepted on 10 Nov 2011 and first published on 16 Nov 2011


Article type: Paper
DOI: 10.1039/C1OB06798B
Citation: Org. Biomol. Chem., 2012,10, 1565-1570
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    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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