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.
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.29925 |
| Date | January 1999 |
| Creators | Tateyama, Miho. |
| Contributors | Yaylayan, V. A. (advisor) |
| Publisher | McGill University |
| Source Sets | Library and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada |
| Language | English |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Format | application/pdf |
| Coverage | Master of Science (Department of Food Science and Agricultural Chemistry.) |
| Rights | All items in eScholarship@McGill are protected by copyright with all rights reserved unless otherwise indicated. |
| Relation | alephsysno: 001738019, proquestno: MQ55092, Theses scanned by UMI/ProQuest. |
Page generated in 0.0015 seconds