Issue 8, 2012

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

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

Supplementary files

Article information

Article type
Paper
Submitted
26 Oct 2011
Accepted
10 Nov 2011
First published
16 Nov 2011

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

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements