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Title: Degradation of penicillin sulphoxide
Author: Leong-Lim, Linda Wei Chin
ISNI:       0000 0001 3608 2595
Awarding Body: University of Surrey
Current Institution: University of Surrey
Date of Award: 1986
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The thesis describes three principle investigations of the alkaline and enzymic degradation of penicillin V beta-sulphoxide. (i) Penicillin V beta-sulphoxide was observed to undergo epimerisation at C-6 on treatment with mild aqueous base: the direct epimerisation of the sulphoxide has only previously been observed using esters in non-aqueous solutions. (ii) 3-phenoxyacetamido-1-phenoxyacetylpyrrole was isolated as an alkaline hydrolysis product of VSO: this appears to be the first reported example of the direct degradation of a penicillin derivative to a pyrrole. This compound was then synthesised and compared with the isolated product. (iii) Comparative studies of the degradation of penicillin V sulphoxide by beta-lactamase and alkali indicated the possible operation of different pathways: this contrasts with the corresponding degradations of penicillin V which were indistinguishable. These investigations are discussed in the context of earlier studies of beta-lactam degradation which are reviewed in an introductory chapter.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: Organic chemistry