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Dissertations / Theses on the topic 'Isopenicillin N'

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Published: 4 June 2021
Last updated: 1 February 2022

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1

Fujishima, Yoshiyuki. "Studies on isopenicillin N synthase." Thesis, University of Oxford, 1992. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.305979.

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2

Bradley, Mark. "Mechanism of isopenicillin N synthase." Thesis, University of Oxford, 1989. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.236117.

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3

Furuse, Reiko. "Mechanistic investigations into isopenicillin N synthase." Thesis, University of Oxford, 1992. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.305450.

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4

Daruzzaman, Adam. "Mechanistic studies on isopenicillin N synthase." Thesis, University of Oxford, 2002. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.289399.

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5

Turner, N. J. "Mechanistic studies on isopenicillin N synthase." Thesis, University of Oxford, 1985. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.355820.

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6

Abbott, Shaun Douglas. "Mechanistic studies on isopenicillin N synthase." Thesis, University of Oxford, 1991. https://ora.ox.ac.uk/objects/uuid:0124fa37-2d7a-43b5-a3e9-c49be4125be2.

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The mechanism of penicillin formation through the action of the enzyme isopenicillin N synthase (IPNS) on the substrate δ-(L-α-aminoadipoyl)-L-cysteinyl-D-valine and synthetic analogues, still raises many unresolved questions, despite many years' extensive investigation. In order to investigate the stereochemistry of formation of the second ring in the product, N-δ-(L-α-aminoadipoyl)-3α-hydroxymethylpenicillin, resulting from incubation of δ-(L-α-aminoadipoyl)- L-cysteinyl-D-vinylglycine with IPNS, the deuterium labelled tripeptides δ-(L-α-aminoadipoyl)- L-cysteinyl-E-[3,4-2H2]-D-vinylglycine and δ-(L-α-aminoadipoyl)-L-cysteinyl- Z-[3,4-2H2]-D-vinylglycine were synthesised and incubated with recombinant IPNS. The pattern of deuterium labelling was retained in the penam products, indicating stereospecific ring closure. The unlabelled and labelled penicillins were converted to their corresponding γ-lactones, and the 1H NMR coupling constants for the C(3)H-C(8)H2 system used to assign the 8-Pro/? and 8-ProS resonances of the unlabelled lactone. Comparison with the labelled lactones indicated that the parent penicillins had been formed via syn addition of sulphur and oxygen across the double bonds of the respective tripeptides. This stereochemistry is consistent with a mechanism involving [2πs + 2π] cycloaddition of an Fe=O species to the olefln.
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7

Fung, Kwok Wing. "Models and mimics of Isopenicillin N Synthase." Thesis, University of Oxford, 1993. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.335777.

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8

Pitt, A. R. "Stereochemistry and mechanism of isopenicillin N synthase." Thesis, University of Oxford, 1988. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.235052.

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9

Brown, Toby James Neville. "Analytical studies of some amino acid secondary metabolism." Thesis, University of Oxford, 1999. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.300806.

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10

Fletcher, Clare Alison. "Studies on the mechanism of isopenicillin-n-synthase." Thesis, University of Oxford, 1993. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.239289.

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11

Henry, Jennifer A. "Peptide synthesis in relation to isopenicillin N synthase." Thesis, University of Edinburgh, 1991. http://hdl.handle.net/1842/12076.

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The preparation of two compounds designed to mimic the active site of Isopenicillin N Synthase (IPNS) is presented. Both compounds consist of two fragments from the enzyme linked by a lipophilic unit. The first contains a short linker unit namely 11-aminoundecanoic acid and the second contains a longer linker consisting of three of these units. The compounds were prepared by solid phase peptide synthesis and purified using a combination of gel permeation chromatography and Phenyl Sepharose hydrophobic interaction chromatography. These compounds have been examined in a two phase system of n-octane and aqueous buffer, containing the IPNS cofactors and tripeptide substrate. The postulated mimic would involve the lipophilic linker unit residing in the organic phase, thus holding the two peptides in close proximity in the aqueous phase. It was hoped that the addition of the Fe2+ cofactor might promote the adoption of a structure resembling that of the enzyme active site. Cyclisation of the penicillin precursors ACV and PCV has not been observed under the conditions investigated, however the compound containing the short linker has been observed to bind iron. Work on immunological studies on IPNS fragments has resulted in the preparation of anti-sera to the N-terminal peptide (IPNS(1-21). These anti-sera have been shown to bind to the peptides IPNS(1-21) and Cys-IPNS(1-21) in an ELISA test and have also been used to detect the native enzyme IPNS by the Western blot method.
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12

Sami, Malkit. "Modification of iron binding ligands in isopenicillin N synthase." Thesis, University of Oxford, 1998. http://ora.ox.ac.uk/objects/uuid:fae89f76-345a-4c57-a37d-a78db8885be7.

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Isopenicillin N synthase (IPNS) is a non-haem iron dependent dioxygenase which catalyses the oxidative conversion of anddelta;-(L-andalpha;-aminoadipoyl)-L-cysteinyl-D-valine (ACV) to isopenicillin N (IPN). Sequence comparisons between IPNS isozymes reveal the complete conservation of two histidine (His214, His270), one aspartate (Asp216) [also known as the '2-His-l-carboxylate' motif] and one glutamine (Gln330) residue. The crystal structure of IPNS (Aspergillus nidulans) active site (in the absence of ACV) revealed an octahedrally coordinated manganese atom surrounded by these four protein ligands and two water molecules. The role of the four conserved metal binding ligands was investigated using site directed mutagenesis. The results demonstrated that ligation of the iron with Gln330 was not essential for the catalytic activity of IPNS. In contrast, ligation of the iron with the three remaining metal ligands was indispensable for catalytic activity. Additionally, it was demonstrated that the conserved Asp216 residue may be substituted by a glutamate residue (D216E) with significant retention of catalytic activity. Crystallographic and spectroscopic evidence suggested that the D216E mutant bound both iron and ACV in a similar way to wild-type IPNS. The inactivation of wild-type IPNS was examined under in vitro assay conditions. This study showed that inactivation of IPNS results (minimally) from a slow non-oxidative pathway (in buffer alone) and a fast oxidative pathway via Udenfriend's chemistry (ferrous iron, ascorbate, and oxygen). The oxidative inactivation pathway was substantially reduced by the inclusion of catalase in the assay mixture, thus indicating that oxidative IPNS inactivation results (in part) from the generation of hydrogen peroxide in solution. Inactivation was also accompanied by a slow fragmentation of intact IPNS into (at least) five oligopeptides (observed by sodium dodecyl sulphate polyacrylamide gel electrophoresis). N-Terminal sequencing analyses confirmed that the fragmentation resulted from at least two cleavage sites within the active site (between Asp216-Val217 and Val272-Lys273).
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13

Ge, Wei. "Crystallographic studies on the mechanism of isopenicillin N synthase." Thesis, University of Oxford, 2006. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.670188.

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14

Rutledge, Peter Jonathan. "Structural studies on the reaction cycle of isopenicillin N synthase." Thesis, University of Oxford, 1999. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.325787.

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15

Howard-Jones, Annaleise R. "Crystallographic studies on the reaction cycle of isopenicillin N synthase." Thesis, University of Oxford, 2004. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.413509.

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16

Smith, Andrew W. "The isopenicillin N synthetase (IPNS) gene (pcbC) : promotor of Acremonium chrysogenum." Thesis, University of Nottingham, 1990. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.258234.

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17

Bainbridge, Zoe. "The purification and characterisation of isopenicillin N synthetase from strains of penicillium chrysogenum." Thesis, University of Westminster, 1994. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.385000.

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18

Ferguson, Amanda Claire. "Total svnthesis of 2-thiabicyclo[3.2.0]heptan-6-one analogues of penicillin N and isopenicillin N for crystallographic studies." Thesis, University of Oxford, 2003. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.398122.

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19

Graf, Paul. "Zur Biosynthese von Isopenicillin N : Zum stereochemischen Verlauf der von Pseudomonas oleovorans katalysierten Epoxidation von Olefinen /." Zürich, 1986. http://e-collection.ethbib.ethz.ch/show?type=diss&nr=8162.

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20

Mazacek, Jan. "Synthese von (D)- und (L)-Alanin mit chiraler Methylgruppe und Einsatz des (D)-Isomeren für Untersuchungen mit Isopenicillin N Synthase /." [S.l.] : [s.n.], 1992. http://e-collection.ethbib.ethz.ch/show?type=diss&nr=9861.

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21

Doherty, Claire. "The use of directed evolution towards altering the substrate specificity of acyl-coenzyme A : isopenicillin N acyl transferase and transforming it from generalist to specialist." Thesis, University of Manchester, 2011. https://www.research.manchester.ac.uk/portal/en/theses/the-use-of-directed-evolution-towards-altering-the-substrate-specificity-of-acylcoenzyme-a-isopenicillin-n-acyl-transferase-and-transforming-it-from-generalist-to-specialist(48bdd12d-f8dd-4bb1-b31b-dae1139cea97).html.

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Acyl Coenzyme A: Isopenicillin N Acyl Transferase (AT) is a key enzyme in the biosynthesis of β-lactam antibiotics in penicillin producing organisms such as P. chrysogenum and A. nidulans. Its natural activity is to exchange the side chain of the low activity antibiotic IPN [18] for the phenylacetyl side chain resulting in the more active antibiotic Penicillin G [5]. The biosynthesis of β-lactams has been exploited towards producing these compounds for therapeutic use. However, increasing bacterial resistance means new analogues in this compound class are constantly sought.As well as improving current production methods of β-lactam antibiotics, AT's broad substrate specificity means it could potentially play a role in the development and production of alternative β-lactam antibiotics that are able to overcome resistance.This thesis describes the identification of an AT mutant with improved acylation activity (AAT activity) via screening of an AT library using a previously developed screening method. Approaches towards the development of a method for the identification of AT mutants with improved hydrolysis activity were also explored. The main problem to overcome in developing such a screen is the inhibitory effect of 6-APA [1], the product of hydrolysis, on AT's IAT activity. The first approach investigated the potential of increasing the sensitivity of an assay by targeting AT to the periplasm. A second approach using β-lactamases to hydrolyse 6-APA [1] thus freeing up the active site of AT was also investigated.
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22

Brüggemann, Tobias [Verfasser]. "Quantenchemische Untersuchungen zu der enzymatischen Wirkungsweise der Isopenicillin-N-Synthase bei der Isopenicillin-N-Synthese und zu cyclischen Stannylsilanen / eingereicht von Tobias Brüggemann." 2004. http://d-nb.info/998358347/34.

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