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Use of shift reagent with MTPA derivatives in 1H NMR spectroscopy. IV. Determination of absolute configuration and enantiomeric purity of amino acid derivatives.

✍ Scribed by Fujiko Yasuhara; Kuninobu Kabuto; Shozo Yamaguchi

Publisher
Elsevier Science
Year
1978
Tongue
French
Weight
282 KB
Volume
19
Category
Article
ISSN
0040-4039

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✦ Synopsis

Determination of absolute configuration and enantiomeric purity of d-amino acids using chemical shift nonequivalence has been well investigated, 132 while little was reported3 on the successful application correlating the absolute configuration of amino acids with their relative magnitude of lanthanide induced shift (LIS). In the previous investigation, we have found that the MTPA ester/Eu(fod)S method for determining absolute configuration and enantiomeric purity of primary and secondary carbinols can be also used for the case where an additional functional group such as OMe is in the carbinyl moiety of the MTPA esters.4 This observation prompted us to investigate the extention of this method to amino acid derivatives. A shift study was carried out on a diastereomeric mixture (0.1 mmol) of (R)-(+)-and (s)-(-)-MTPA [d-methoxy-0(-trifluoromethylphenylacetic acid, Mosher's Reagent'] amides of L-

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