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Chiral α ‐Amino Acid‐Based NMR Solvating Agents
Author(s) -
Nemes Anikó,
Csóka Tamás,
Béni Szabolcs,
Garádi Zsófia,
Szabó Dénes,
Rábai József
Publication year - 2020
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.202000081
Subject(s) - chemistry , ethylamine , reagent , valine , alanine , chiral derivatizing agent , amino acid , leucine , stereochemistry , organic chemistry , enantiomer , chiral column chromatography , biochemistry
Four new chiral α ‐(nonafluoro‐ tert ‐butoxy)carboxylic acids were synthesized from naturally occurring α ‐amino acids (alanine, valine, leucine and isoleucine, respectively), and tested in 1 H‐ and 19 F‐NMR experiments as chiral NMR shift reagents. The NMR studies were carried out at room temperature, using CDCl 3 and C 6 D 6 as solvents, and ( RS )‐ α ‐phenylethylamine and ( RS )‐ α ‐(1‐naphthyl)ethylamine as racemic model compounds. To demonstrate the applicability of the reagents, the racemic drugs ketamine and prasugrel were also tested.