Doctoral Dissertations

Author

Jo Dee Duncan

Abstract

"The problem addressed by this dissertation is the separation of optical isomers in commercial as well as biological samples. The chromatographic separation of enantiomers is an important and rapidly developing field of study. Chiral separations of pharmaceutical compounds and important organic intermediates in high performance liquid chromatography (HPLC) and thin layer chromatography (TLC) were achieved. Two methods were employed for the direct liquid chromatographic resolution of chiral analytes: chiral stationary phases (CSPs) and chiral mobile phase additives (CMAs). Native and derivatized ß-cyclodextrins (ß-CD) were used as chiral stationary phases in reverse phase and normal phase HPLC, respectively. This study marked the first use of derivatized ß-CDs for chiral separations in normal phase media. N-carbobenzoxy-glycl-L-proline and (1R)-(-)ammonium-10-camphorsulfonate were utilized as CMAs in normal phase TLC for the resolution of several aromatic amino alcohols. Maltosyl-ß-CD and hydroxypropyl-ß-CD were employed as CMAs in reverse phase TLS. A study was conducted with hydroxypropyl-ß-CD to determine how the degree of substitution of a derivatized CD could effect development time, the viscosity of the solution and the enantioselectivity. In addition, studies were initiated to determine the presence of trace levels of D-amino acids in: amniotic fluid, blood serum and urine. The blood and urine of healthy young adults were analyzed and found to contain trace to percent levels of D-amino acids. The human amniotic fluid samples did not have detectable levels of D-amino acids"--Abstract, page iv.

Advisor(s)

Armstrong, Daniel Wayne

Committee Member(s)

Manuel, O. (Oliver), 1936-
Stoffer, James O.
Bertrand, Gary L.
Benjamin, Colin

Department(s)

Chemistry

Degree Name

Ph. D. in Chemistry

Publisher

University of Missouri--Rolla

Publication Date

1991

Pagination

xi, 130 pages

Note about bibliography

Includes bibliographical references (pages 123-129).

Rights

© 1991 Jo Dee Duncan, All rights reserved.

Document Type

Dissertation - Open Access

File Type

text

Language

English

Library of Congress Subject Headings

Enantiomers -- Separation
Chromatographic analysis
Optical isomers
Optical isomers -- Biotechnology

Thesis Number

T 6316

Print OCLC #

26275152

Electronic OCLC #

857066834

Included in

Chemistry Commons

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