Thesis (B. Sc.(Hons.))--University of Queensland, 2002. / Includes bibliographical references.

Amadori and Heyns rearrangement products are currently produced as crude Maillard reaction mixtures, due to lack of convenient procedures for their synthesis. The objective of this study was to develop a synthetic strategy based on polymer-supported synthesis that allows the production of different derivatives of these sugar-amino acid conjugates. The strategy involved coupling of poly(ethyleneglycol) mono methyl ether (PEGME) with N-protected (t-BOC) amino acid through catalysis by DCC (dicyclohexylcarbodimide) to form a polymer bound ester of the amino acid (89% yield with beta-alanine), followed by deprotection of the t-BOC group through a novel microwave-assisted hydrolysis process in high yields (98%). After the deprotection, the polymer-based amino acid was neutralized by triethyl amine treatment, followed by room temperature reaction with selected reducing sugars or sugar analogs, for 48 hrs to produce polymer bound ARP in 75% yield (using acetol). The final product was cleaved by methanolysis using sodium methioxide in 65% yield. The reactions were monitored by spectroscopic analysis and the intermediates were identified by FTIR, Py/GC/MS and 1H NMR.

A water-methanol solution of glycine and scD-glucose was refluxed for seven hr. The solvent was evaporated under vacuum at room temperature and the residue was dialyzed against distilled water. After dialysis, the solvent was evaporated under vacuum at room temperature. The non-dialyzable fraction was further fractionated by gel filtration. The process yielded three polymeric materials (10,000 $<$ M $<$ 20,000) whose purity was verified by HPLC. The isolated polymers were further analyzed by UV-VIS and FTIR spectroscopy and by pyrolysis/GC/MS. Elemental analysis indicated that polymer A has the following empirical formula $ rm C sb6H sb{11}N sb1O sb4$ and polymers B1 and B2 have the same empirical formula as glucose $ rm C sb1H sb2O sb1.$ The origin of nitrogen containing polymer A was assigned to Amadori intermediate or to some of its derivatives and the origin of polymers B1 and B2 was assigned to Glucosone and to 3- or 1-deoxyglucosones; common non-nitrogen containing reactive intermediates during Maillard reaction. Plausible mechanisms were proposed for the formation of polymers.

v, 234 leaves : tables ; 28 cm. / Title page, contents and abstract only. The complete thesis in print form is available from the University Library. / Thesis (Ph.D.1974) from the Dept. of Psychology, University of Adelaide

Thesis (B.A. Hons. 1971) from the Department of Psychology, University of Adelaide.

Thesis (Ph. D.)--Columbia University, 1922. / Vita. "Reprinted from Archives of psychology ... no. 54."

Thesis (Ph. D.)--Johns Hopkins University, 1912. / Vita. Published also as Psychological review publications. The psychological monographs, vol. 15, no. 5; whole no. 66. Bibliography: p. [67]-69.

Thesis (Ph. D.)--University of Wisconsin--Madison, 1961. / Typescript. Vita. eContent provider-neutral record in process. Description based on print version record. Includes bibliographical references.

Thesis (M.S.)--University of Wisconsin--Madison, 1974. / Vita. eContent provider-neutral record in process. Description based on print version record. Includes bibliographical references.

Thesis--University of Wisconsin--Madison. / Typescript. Vita. eContent provider-neutral record in process. Description based on print version record. Includes bibliographical references (leaves 65-69).