Enhanced Stereochemical Analysis of β‑Diastereomeric Amino Acids with Variants of Marfey's Reagent.

ABSTRACT: The analysis of mixtures of amino acid stereoisomers is a classic challenge in bioorganic chemistry and organic synthesis. Chemical derivatization with Marfey's reagent, 1-fluoro-2,4-dinitrophenyl-5-l-alanine amide, is frequently employed as chromatographic separation of the resulting diastereomers enables convenient assignment of d/l-configuration and determination of enantiomeric ratio. However, it is often challenging to resolve Cβ-epimeric diastereomers of noncanonical amino acids after treating with Marfey's reagent. This report describes the effectiveness of alternative chiral derivatization reagents. We demonstrate that the Cβ epimers of l-phenylserine and other β-hydroxy noncanonical l-amino acids are more easily separated when the traditional Marfey's reagent is substituted by a p

SUBMITTER: Studinski CI 

PROVIDER: S-EPMC12593104 | biostudies-literature | 2025 Nov

REPOSITORIES: biostudies-literature