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

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

doi:10.1039/C1OB06798B

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Organic & Biomolecular Chemistry

Issue 8, 2012

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

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

Org. Biomol. Chem., 2012, 10, 1565-1570

DOI: 10.1039/C1OB06798B
Received 26 Oct 2011, Accepted 10 Nov 2011
First published on the web 16 Nov 2011
This article is part of the collection: Organocatalysis

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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.

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

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Organic & Biomolecular Chemistry

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

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