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Title: Chemo-enzymatic approaches to morphine-6-glucuronide and selected analogues
Author: Brady, Sarah Catherine
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 1998
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Morphine 1 is metabolised in the liver into its active form, morphine-6-glucuronide (M6G) 2. When M6G 2 is administered directly to patients it has greater analgesic potency than morphine 1 and this stimulated interest in the synthesis of M6G 2 as a novel analgesic. We have examined several synthetic routes to the precursor morphine-6-glucoside 4 with selective oxidation to M6G 2 as the final step. (Fig. 10917A). The coupling of a glucose residue to morphine 1 was investigated using both chemical and enzymatic approaches. However, selective oxidation at the C6' position of morphine-6-glucoside 4 did not yield the desired metabolite M6G 2. The replacement of the glucose reside in scheme 1 by galactose and arabinose gave morphine-6-glucoside analogues which are potentially an alternative source of analgesics. (Fig. 10917B).
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available