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Degradation of penicillin sulphoxide.

Leong-Lim, Linda Wei Chin. (1986) Degradation of penicillin sulphoxide. Doctoral thesis, University of Surrey (United Kingdom)..

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Abstract

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.

Item Type: Thesis (Doctoral)
Divisions : Theses
Authors :
NameEmailORCID
Leong-Lim, Linda Wei Chin.
Date : 1986
Contributors :
ContributionNameEmailORCID
http://www.loc.gov/loc.terms/relators/THS
Additional Information : Thesis (Ph.D.)--University of Surrey (United Kingdom), 1986.
Depositing User : EPrints Services
Date Deposited : 22 Jun 2018 13:56
Last Modified : 06 Nov 2018 16:53
URI: http://epubs.surrey.ac.uk/id/eprint/847636

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