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Synthesis of glucuronic-acid conjugates of hydroxylated metabolites of a new local anaesthetic
2000 (English)Independent thesis Basic level (professional degree)Student thesis
Abstract [en]

Synthesis of glucuronic-acid conjugates of hydroxylated metabolites of a new local anaesthetic Carl Johan Arewång 2000-02-21 Supervisors: Doctor Anna-Karin Tidén Assoc. Professor Ian McEwen. Diploma thesis work (20p) for the University of Karlstad Performed at: AstraZeneca R&D Södertälje, Department of Chemistry. The synthesis of two glucuronides, thought to be derived from a new local anaesthetic, is described. Several methods and reaction conditions were investigated. The most successful approach was the coupling of the two aglycons (one phenol and one secondary alcohol) with methyl 2,3,4-tri-O-benzoyl-1-bromo-1-deoxy-1-a-D-glucopyranoate promoted by silver triflate. Both the aglycons have an amine-group present, however this did not cause any problems in the glycosylation reactions. The desired fully protected glucuronides were obtained as b-anomers only. The yields for the coupling reactions were good compared with the literature, 40% yield in the phenol coupling reaction and 75% yield in the alcohol coupling reaction. The two protected b-glucuronides were successfully deprotected to give the desired tentative metabolites. The synthesised phenol-glucuronide was identical with the metabolite isolated from human urine, whereas the synthesised alcohol-glucuronide did not correspond to any metabolite extracted from human urine.

Place, publisher, year, edition, pages
2000. , 27 p.
Identifiers
URN: urn:nbn:se:kau:diva-52405Local ID: KEM-10OAI: oai:DiVA.org:kau-52405DiVA: diva2:1100931
Subject / course
Chemistry
Available from: 2017-05-29 Created: 2017-05-29

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