{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Salib MN"],"funding":["Division of Chemistry","National Center for Research Resources","NCRR NIH HHS","NIAID NIH HHS","National Institutes of Health"],"pagination":["3269-3278"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC11894641"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["90(9)"],"pubmed_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 <i>S</i><sub>N</sub>Ar 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 (<b>4</b>) in which the l-alanine-derived auxiliary is replaced by l-tryptophanamide and (<i>S</i>)-FDNE (<b>3</b>) where the auxiliary is <i>S</i>-(6-methoxynaphth-2-yl)-1-ethylamine. Side-by-side comparisons of the two reagents were carried out by"],"journal":["The Journal of organic chemistry"],"pubmed_title":["Synthesis and Performance of l-Tryptophanamide and (&lt;i&gt;S&lt;/i&gt;)-1-(Naphthalen-2'-yl)ethanamine-Based Marfey-Type Derivatives for Amino Acid Configurational Analysis: Diastereomeric Resolutions Directed by π-Cation Bonding."],"pmcid":["PMC11894641"],"funding_grant_id":["S10RR025636","R01 AI1007786","CHE0741968","S10 RR025636","R01 AI100776"],"pubmed_authors":["Salib MN","Molinski TF"],"additional_accession":[]},"is_claimable":false,"name":"Synthesis and Performance of l-Tryptophanamide and (&lt;i&gt;S&lt;/i&gt;)-1-(Naphthalen-2'-yl)ethanamine-Based Marfey-Type Derivatives for Amino Acid Configurational Analysis: Diastereomeric Resolutions Directed by π-Cation Bonding.","description":"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 <i>S</i><sub>N</sub>Ar 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 (<b>4</b>) in which the l-alanine-derived auxiliary is replaced by l-tryptophanamide and (<i>S</i>)-FDNE (<b>3</b>) where the auxiliary is <i>S</i>-(6-methoxynaphth-2-yl)-1-ethylamine. Side-by-side comparisons of the two reagents were carried out by","dates":{"release":"2025-01-01T00:00:00Z","publication":"2025 Mar","modification":"2025-04-06T22:39:44.593Z","creation":"2025-04-04T02:54:22.742Z"},"accession":"S-EPMC11894641","cross_references":{"pubmed":["39977842"],"doi":["10.1021/acs.joc.4c02882"]}}