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The 21-dehydroxglation of corticosteroids of Eubacterium lentum and the dehalogenation of 4-chlorobenzoic acid by 4-chlorobenzoate dehalogenase

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dc.contributor.author Ninniss, Ronald William. en_US
dc.date.accessioned 2009-11-04T14:55:21Z
dc.date.available 2009-11-04T14:55:21Z
dc.date.issued 1988-11-04T14:55:21Z
dc.identifier.uri http://hdl.handle.net/10464/2816
dc.description.abstract Two enzyme mechanisms were investigated: the 21-dehydroxylation of corticosteroids by Eubacterium lentum and the dehalogenation of 4-chlorobenzoic acid by Pseudomonas sp. CBS 3. , Chemical and enzymic methods of reduction of 21-oxo steroids were used to generate C-21-d1 compounds of tetrahydrodeoxycorticosterone, with both predominant stereochemistries. It was found that during the dehydroxylation the pro-S hydrogen at the C-21 position was lost preferentially. This suggests that the enzyme removes the pro-S hydrogen during binding to the active site as the ene-diol. To study the hydrolytic replacement of chlorine by hydroxyl , p-chlorobenzoic acid-d4 was prepared and sent to Germany for an ~ncubation with an enzyme preparation of 4-Chlorobenzo~te Dehalogenase. Results suggests the possible loss of deuterium during the conversion of p-chlorobenzoate to p-hydroxybenzoate, from all four ring positions. Many methods of preparing the control compound p-hydroxybenzoic acid-d4 were investigated. en_US
dc.language.iso eng en_US
dc.publisher Brock University en_US
dc.subject Adrenocortical hormones. en_US
dc.subject Eubacterium lentum. en_US
dc.subject Chlorobenzoate dehalogenase. en_US
dc.subject Hydroxylation. en_US
dc.subject Halogenation. en_US
dc.subject Benzoic acid. en_US
dc.title The 21-dehydroxglation of corticosteroids of Eubacterium lentum and the dehalogenation of 4-chlorobenzoic acid by 4-chlorobenzoate dehalogenase en_US
dc.type Electronic Thesis or Dissertation en_US
dc.degree.name M.Sc. Chemistry en_US
dc.degree.level Masters en_US
dc.contributor.department Department of Chemistry en_US
dc.degree.discipline Faculty of Mathematics and Science en_US


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