Synthesis and Performance of l-Tryptophanamide and (<i>S</i>)-1-(Naphthalen-2'-yl)ethanamine-Based Marfey-Type Derivatives for Amino Acid Configurational Analysis: Diastereomeric Resolutions Directed by π-Cation Bonding.

ABSTRACT: The configurational analysis of amino acids (AAs) in natural product peptides, often containing nonproteinogenic AAs, is mostly carried out by the venerable Marfey's method using a chiral derivatizing agent (CDA) 1-fluoro-2,4-dinitrophenyl-5-l-alaninamide (l-FDAA)─Marfey's reagent─which undergoes S_NAr reaction of the 1° amino group. The resulting AA-DAA derivatives are mostly well-separated by reversed-phase HPLC, but some DAA derivatives resist resolution. Here, we report the synthesis and characterization of two CDAs: l-FDTA (4) in which the l-alanine-derived auxiliary is replaced by l-tryptophanamide and (S)-FDNE (3) where the auxiliary is S-(6-methoxynaphth-2-yl)-1-ethylamine. Side-by-side comparisons of the two reagents were carried out by

SUBMITTER: Salib MN 

PROVIDER: S-EPMC11894641 | biostudies-literature | 2025 Mar

REPOSITORIES: biostudies-literature