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Cristiano Bolchi1, Gabriella Roda2, Marco Pallavicini2

  • 1Dipartimento di Scienze Farmaceutiche, Sezione "Pietro Pratesi", Università degli Studi di Milano, via Mangiagalli 25, 20133, Milan, Italy. cristiano.bolchi@unimi.it.

Amino Acids
|September 19, 2018
PubMed
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1H NMR with a chiral solvating agent offers a rapid method for determining the enantiomeric purity of amino acid benzyl esters. This technique accurately quantifies enantiomeric excess for several compounds, providing an alternative to chiral HPLC.

Area of Science:

  • Organic Chemistry
  • Analytical Chemistry

Background:

  • Amino acid benzyl esters are valuable chiral building blocks.
  • Their enantiomeric purity is crucial but challenging to verify due to racemization risks.

Purpose of the Study:

  • To explore 1H NMR spectroscopy with a chiral solvating agent (CSA) as an alternative to chiral HPLC for determining enantiomeric purity.
  • To investigate the enantiodiscrimination of 13 amino acid benzyl esters using (R)-Mosher acid as a CSA.

Main Methods:

  • Utilized 1H NMR spectroscopy in the presence of (R)-Mosher acid.
  • Tested various solvents to optimize enantiodifferentiation.
  • Analyzed spectral non-equivalence of protons to determine enantiomeric composition.

Main Results:

Keywords:
1H NMR spectroscopyAmino acid benzyl esterChiral solvating agent (CSA)EnantiodiscriminationMosher’s acid

Related Experiment Videos

  • Achieved efficient enantiodifferentiation for 5 amino acid benzyl esters (Ala, Pro, Glu, Met, Ser).
  • Accurately determined enantiomeric excesses up to 98%.
  • Identified protons on the α-carbon, methyl groups, β-carbon, and benzylic carbon as useful for enantiodifferentiation.

Conclusions:

  • 1H NMR with CSA provides a viable, rapid, and accurate method for assessing enantiomeric purity of certain amino acid benzyl esters.
  • Low steric hindrance at the amino acid β-carbon appears to favor enantiodiscrimination.