Mechanism of pH-Dependent Photolysis of Aliphatic Amino Acids and Enantiomeric Enrichment of Racemic Leucine by Circularly Polarized Light

It has been proposed that the origin of biological homochirality may be the result of irradiation of a racemic sample of amino acids by circularly polarized light (CPL). To determine the mechanism of enantiomeric enrichment, the irradiation of aliphatic amino acids by CPL was undertaken. An enantiom...

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Bibliographic Details
Published in:Organic letters 2001-03, Vol.3 (6), p.921-924
Main Authors: Nishino, Hideo, Kosaka, Atsuko, Hembury, Guy A, Shitomi, Hiroshi, Onuki, Hideo, Inoue, Yoshihisa
Format: Article
Language:English
Subjects:
Amino Acids - chemistry
Amino Acids - radiation effects
Circular Dichroism
Hydrogen-Ion Concentration
Kinetics
Leucine - chemistry
Leucine - radiation effects
Molecular Conformation
Photolysis
Stereoisomerism
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Summary:It has been proposed that the origin of biological homochirality may be the result of irradiation of a racemic sample of amino acids by circularly polarized light (CPL). To determine the mechanism of enantiomeric enrichment, the irradiation of aliphatic amino acids by CPL was undertaken. An enantiomerically enriched sample (e.g., l isomer enrichment from r-CPL) was found to result from the preferential excitation/decomposition of one enantiomer over another via a Norrish Type II mechanism (leucine, valine, and isoleucine), with the enantiomeric excess dependent on the degree of protonation of the amino/carboxylic acid moiety.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0155788