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Date of Award
1997
Document Type
Thesis - Pacific Access Restricted
Degree Name
Master of Science (M.S.)
Department
Chemistry
First Advisor
Michael J. Minch
First Committee Member
Donald K. Wedegaertner
Second Committee Member
Charles A. Matuszak
Third Committee Member
Vyacheslav Samoshin
Abstract
Ornithine is an amino acid of which the side chain contains three pairs of diastereotopic protons. The diastereotopic protons are chemically nonequivalent. The NOEDIF spectra of ornithine were obtained in an acid solution to assign the individual chemical shifts of the β diastereotopic protons with the aid of the theoretical calculation of conformation distribution. The β Pro-S resonance was found to be at a higher field than β pro-R proton.
(S,S)-Ethylenediamine-N,N'-disuccinic acid (EDDS) was found to be a good chiral chemical shift reagent ligand in water solution. The Ytterbium complex of EDDS was used to distinguish L-ornithine and D-ornithine. For the α protons, the enantiomeric shift difference was affected by the pH of the solution and the substrate : Yb(EDDS)’ ratio. The association constants between Yb(EDDS)’ and L- or D-ornithine were found to be slightly different. Yb(EDDS)’ may also be useful to distinguish between the diastereotopic protons in ornithine and other molecules in NMR spectra.
Pages
84
Recommended Citation
Zhao, Jianzhou. (1997). ¹H NMR study of ornithine and the development of Yb(EDDS), an aqueous chiral chemical shift reagent. University of the Pacific, Thesis - Pacific Access Restricted. https://scholarlycommons.pacific.edu/uop_etds/2322
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