Use this URL to cite or link to this record in EThOS: http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.660397
Title: Investigations into the biosynthesis of carbocyclic nucleosides by Streptomyces citricolor
Author: Paterson, Nicola Margaret
Awarding Body: University of Edinburgh
Current Institution: University of Edinburgh
Date of Award: 2000
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Abstract:
Aristeromycin 4 and neplanocin A 5 are biologically active carbocyclic nucleosides produced by the organism Streptomyces citricolor. Previous studies towards elucidating their biosynthesis have led to a proposed biosynthetic pathway in which D-glucose is converted via a number of carbocyclic intermediates to neplanocin A and aristeromycin. This thesis describes the studies that have been carried out in order to: i. identify the first formed carbocyclic intermediate on the biosynthetic pathway (Chapter 2). ii. determine the identity of the phosphorylated intermediates prior to neplanocin A (Chapter 3). The novel (2R, 3S, 4R) and (2R, 3S, 4S) keto-tetrols 95, ent-95 and 116 have been prepared and their syntheses are described. To determine whether those intermediates lie on the biosynthetic pathway, feeding studies have been carried out using a mutant of Streptomyces citricolor. The results of these studies, described within, suggest that both the (2R, 3S, 4R) keto-tetrol 95 and its diastereomer (2R, 3S, 4S) keto-tetrol 116 lie on the biosynthetic pathway. The syntheses of the known intermediate tetrol 83a, the proposed phosphorylated intermediate 5-phosphate 83b and the corresponding 1-phosphate 152, via multi-step syntheses from the cyclopentenone 61, prepared from either D-ribose 126 or cyclopentadiene 36, are described.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID: uk.bl.ethos.660397  DOI: Not available
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