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

The international home of synthetic, physical and biomolecular organic chemistry.

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

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

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Department of Chemistry, University of York, Heslington, UK
E-mail: paul.clarke@york.ac.uk

School of Chemistry, University of Nottingham, University Park, Nottingham, UK
E-mail: chris.hayes@nottingham.ac.uk

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

DOI: 10.1039/C1OB06798B
Received 26 Oct 2011, Accepted 10 Nov 2011
First published online 16 Nov 2011

This article is part of themed 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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