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Molecular Chirality in Chemistry and Biology: Historical Milestones
Author(s) -
Gal Joseph
Publication year - 2013
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201300300
Subject(s) - chemistry , chirality (physics) , enantiomer , enantioselective synthesis , stereochemistry , tartaric acid , organic chemistry , catalysis , citric acid , physics , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , quark
Beginning early in the 19th century, developments in crystallography, optics, and chemistry in France set the stage for the discovery of molecular chirality by Louis Pasteur in 1848. He found that the crystallization of the sodium ammonium salt of ‘ paratartaric acid ’, a mysterious ‘ isomer ’ of natural (+)‐tartaric acid (TA), produced two different crystal types that were non‐superimposable mirror‐image forms of each other. He separated the two types and found their optical rotations in solution opposite in direction and equal in absolute magnitude. This led him to conclude that paratartaric acid is a combination of two mirror‐image molecule types of TA that are ‘ dissymmetric ’, an existing term he adapted to the connotation of today's ‘ chiral ’. In 1857, he found that the two enantiomers of TA were metabolized by a microorganism at drastically different rates, and thereby discovered biological enantioselectivity. In 1886, Italian chemist Arnaldo Piutti discovered D ‐asparagine and found that it tasted intensely sweet, in contrast to the known L ‐asparagine which had no taste. This was the discovery of stereoselectivity at biological receptors. As a result of advances in stereoselective synthesis and enantioselective chromatography during the last decades of the 20th century, in the 1990s the importance of molecular chirality in drug action and disposition began to receive serious attention from drug‐regulatory authorities and the pharmaceutical industry, the overall result of which has been the near‐complete disappearance of racemic drugs as newly introduced pharmaceuticals.