The Rational Design and Application of New Chiral Phosphonates for the Enantiomeric Excess Determination of Unprotected Amino Acids. Remarkable pH Dependency of the Diastereomeric Shift Differences.

DOI: 10.1016/S0040-4020(01)85665-9

Source and publish data:

Tetrahedron p. 11721 - 11728 (1994)

Update date:2022-08-04

Topics:

Authors:

Hulst, Ron

Vries, N. Koen de

Feringa, Ben L.

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Article abstract of DOI:10.1016/S0040-4020(01)85665-9

Diastereomeric amide derivatives of chiral phosphorinane 8 and unprotected amino acids are easily prepared in aqueous solutions, showing well separated signals in the 31P NMR spectra allowing accurate enentiomeric excess determination.Moreover, the obtained diastereomeric shift dispersion appears to be highly pH dependent, indicating the influence of intramolecular ion pair formation on the diastereomeric shift dispersion.

Full text of DOI:10.1016/S0040-4020(01)85665-9

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