Document Detail


Asymmetric organocatalytic formation of protected and unprotected tetroses under potentially prebiotic conditions.
MedLine Citation:
PMID:  22245755     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
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.
Authors:
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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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-1-16
Journal Detail:
Title:  Organic & biomolecular chemistry     Volume:  -     ISSN:  1477-0539     ISO Abbreviation:  -     Publication Date:  2012 Jan 
Date Detail:
Created Date:  2012-1-16     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101154995     Medline TA:  Org Biomol Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Affiliation:
Department of Chemistry, University of York, Heslington, York, North Yorks, UKYO10 5DD. paul.clarke@york.ac.uk.
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