![]() ![]() Marfey’s derivatives of these epimeric amino acids at C β can be differentiated by their distinct NMR spectra. We describe a new approach based on the extension of Marfey’s analysis using HPLC-SPE-NMR to sort out this challenge. Such is the case of isoleucine and threonine which can also be found in natural nonribosomal peptides as their allo-diastereomers. However, for certain amino acids possessing a second chiral centre at C β, the discrimination between the two possible epimers may still be challenging due to the lack of chromatographic resolution. This approach relies on the complete hydrolysis of the peptide followed by the reaction of the resulting amino acid pool with Marfey’s reagent, a chiral derivatizing agent which turns amino acid enantiomers into diastereomeric pairs which can be resolved by conventional reversed-phase HPLC. The determination of amino acid chirality in natural peptides is typically addressed by Marfey’s analysis. ![]()
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