Sugar-assisted kinetic resolution of amino acids and amplification of enantiomeric excess of organic molecules.
The origins of biological homochirality have intrigued researchers since Pasteur's discovery of the optical activity of biomolecules. Herein, we propose and demonstrate a novel alternative for the evolution of homochirality that is not based on autocatalysis and forges a direct relationship between the chirality of sugars and amino acids. This process provides a mechanism in which a racemic mixture of an amino acid can catalyze the formation of an optically active organic molecule in the presence of a sugar product of low enantiomeric excess.
Córdova
Armando
A
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden. acordova@organ.su.se
Sundén
Henrik
H
Xu
Yongmei
Y
Ibrahem
Ismail
I
Zou
Weibiao
W
Engqvist
Magnus
M
D000438:Alcohols / Q000138:chemical synthesis / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D011392:Proline / Q000737:chemistry; D013237:Stereoisomerism
D000438:Alcohols; D000447:Aldehydes; D000596:Amino Acids; D002241:Carbohydrates; D011392:Proline