Related Experiment Video
Updated: Aug 8, 2026

Split-and-pool Synthesis and Characterization of Peptide Tertiary Amide Library
Published on: June 20, 2014
The kinetics of diastereomeric amino acids with o-phthaldialdehyde
M W Meyer1, V R Meyer, S Ramseyer
1Institute of Organic Chemistry, University of Bern, Switzerland.
Abstract:
The kinetics of the reaction of the amino acid epimers L-isoleucine, D-allo-isoleucine, L-threonine, and D-allo-threonine with o-phthaldialdehyde and mercaptoethanol were determined at 25 degrees 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.
Related Concept Videos
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
Aldol Condensation with β-Diesters: Knoevenagel Condensation
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

