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The kinetics of diastereomeric amino acids with o ‐phthaldialdehyde
Author(s) -
Meyer Marc W.,
Meyer Veronika R.,
Ramseyer Stephan
Publication year - 1991
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530030611
Subject(s) - chemistry , racemization , diastereomer , epimer , isoleucine , amino acid , threonine , chromatography , kinetics , high performance liquid chromatography , stereochemistry , organic chemistry , leucine , biochemistry , serine , enzyme , physics , quantum mechanics
The kinetics of the reaction of the amino acid epimers L ‐isoleucine, D ‐alloisoleucine, L ‐threonine, and D ‐allo‐threonine with o ‐phthaldialdehyde and mercaptoethanol were determined at 25°C. L ‐Isoleucine reacts faster than its D ‐epimer whereas L ‐threonine reacts slightly slower than its D ‐epimer. In the case of isoleucine, the consequence can be an allo/iso ratio which in the worst case is 25% too low if these amino acids are quantified by liquid chromatography and o ‐phthaldialdehyde fluorescence detection. The effect on dating of fossils by amino acid racemization is discussed.