Article

Efficient asymmetric organocatalytic formation of erythrose and threose under aqueous conditions.

Department of Chemistry, University of York, Heslington, York, UK YO10 5DD.
Chemical Communications (impact factor: 6.17). 07/2010; 46(26):4776-8. DOI:10.1039/c0cc00613k pp.4776-8
Source: PubMed

ABSTRACT Esters of proteinogenic amino acids efficiently catalyse the formation of erythrose and threose under aqueous conditions in the highest yields and enantioselectivities yet reported. Remarkably while esters of (L)-proline yield (L)-carbohydrates, esters of (L)-leucine and (L)-alanine generate (D)-carbohydrates, offering the potential to account for the prebiotic link between natural (L)-amino acids and natural (D)-sugars.

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Keywords

aqueous conditions
 
D)-carbohydrates
 
esters
 
L)-amino acids
 
L)-carbohydrates
 
L)-leucine
 
L)-proline yield
 
prebiotic link
 
proteinogenic amino acids
 

Laurence Burroughs