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Aspects of the Radiation Chemistry and Protection of Peptides

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Aspects of the Radiation Chemistry and Protection of Peptides A S P E C T S 0 F T HE R A D I A T I O N C H E M I S T R Y A, N D P R O T E C T I O N O F P E P T I D E S A thesis submitted in partial fulfillment of the requirements for the degree of M A S T E R 0 F S C I E N C E in the University of New South Wales by J.A. HOURIGAN, B.Sc. July, 1971. (11) The work contained in this thesis has not been submitted for a degree or similar award to any other University or Institution. J.A. HOURIGAN (111) Aspects of the radiation chellliatry and protection of the polypeptide chain of catalase were investigated, employing the soluble enz,111le and also insoluble, poly(diazostyrene)-bound catalase. Prior investigation of the structure of the inaolubilized catalase by ion-exchange chromatography of its hydrolysate showed that approximately 140 residues (histidine, lysine, cysteine and tyrosine, i.e. roughly half the total number of these residues per catalase aolecule) were covalently linked to poly(diazostyrene) molecules. The conjugate was pictured as a catalase molecule to which a large number (20-100) of poly(diazostyrene) molecules were covalently linked. The results indicate further, and in agreement with the results of irradiation experiments, that the tyrosine and arginine residues are mainly located in the interior of the active conformer of the catalase molecule. A novel pyrolysis-gas chromatographic technique was developed for the estimation of the protein content of poly(diazostyrene)-bound catalase. The method was calibrated against the results of quantitative ion­ exchange chromatography of the hydrolysates of the bound enzymes. It was then extended to allow the prediction (iv) of the protein content of poly(diazostyrene)-bound catalase prepared by a known procedure from a given ratio of protein to polymeric carrier. The radiation sensitivity of catalase was investigated, first, free in dilute, oxygenated aqueous solution and secondly, bound to poly(diazostyrene) as a dilute, oxygenated, aqueous dispersion. Hydroxyl radicals, resulting from {-irradiated water molecules, inactivated the enzyme and degraded cysteine and/or cystine in particular, amongst the amino acid residues. Although the radical scavenging and repair agent, diglycylglycine, offered some protection against the effects of (-radiation on catalase, protection of similar molar concentrations of catalase by the insolubilization was much more effective, probably due to a combination of conventional radical scavenging and repair processes with proximity, conformational and other steric factors. lV) TABLE o:r CONTENTS TITLE -PAGE 1 • Introduction. 1 1.1 Radiation Effects OD Peptides and Related Compounds. 1 1.2 Radiation Chemistry of Water. 4 1. 3 Radiation Chemistry of Aqueous Solutions. 7 1.4 Mathematical Treatment of Protection. 11 1.5 Catalase. 22 1.6 Insolubilized Enzymes. 24 1.7 The System to be Investigated. 29 2. Experimental Methods 0 30 2.1 Materials. 30 2.2 Apparatus. 33 2.3 Preparation of Insolubilized Catalase. 37 2.4 Properties of Insolubilized Catalase and Constituent Polymers. 42 2.5 Estimation of Catalatic Activity. 46 2.6 The Effects off-Radiation. 49 3. Discussion of Results• 54 3.1 The Radiolytic Inactivation of Catalase in Solution. 54 (vi) Table of Contents (Continued) TITLE -PAGE 3.2 Species Responsible for the Radiolytic Inactivation of Catalase in Solution. 72 3.3 The Properties of Polymer-Bound Catalase. 85 3.4 The Radiolytic Inactivation of Insolubilized Cata.lase. 121 4. Conclusion. 132 5. Acknowledgements. 134 6. References. 136 APPENDIX 1. Results• 148 1.1 Properties of Insolubilized Catalase. 148 1.2 The Effects of '6'-Radiation. 160 2. Published Reaction Rate Constants. 177 2.1 Reactions of the Hydroxyl Radical. 177 2.2 Miscellaneous Reactions. 181 1 • l IftRODUC!IOB l.l IU.D~IOB BPlBCTS OB PEPTIDES ilD BELATED COIIPOUlf.DS !he large volW118 of litera'turel-4 published in the last decade on the radiation cheaistry of peptides and such related substances a■ amino acid■, proteins and enzyaes, is a reflection of the iaportance of this area of investigation. The irradiated materials were aost commonly in the solid state or either in oqgenated or deoqgenated aqueous solutions14• As one facet of this work, many investigators have attempted to protect the irradiated aaterials froa the effects of irradiation5• 6• Protection, in thia sense, occurs when the destniotiv• effect of the irradiation on the compound under study 1• reduced by an added substance. The converse is sensitizat­ ion. The aeohanisa of protection usually falls into on• or other of the categories shown below5- 7• a) Transfer of energy or charge by physical processes can protect an irradiated molecule by removing excess energy before the molecule can decompose. The protector aay then decoapose. This mechanism haa been coaaonly observed during irradiation of organic liquida, particul­ arly when the protector is an aromatic coapound. b) Scavenging of radiation-produced free radicals (See Section 1.2) by protector molecules will sometimes reduce the destructive effect of irradiation. In these instances, the protector is usually a highly reactin coapoUDd towards the radiation-produced free radicals so that it oompetea successfully forth• with the sub­ atrate, even when the former•a concentration is au.eh lower than the latter's• c) A similar effect is obtained if the protector interacts chemically with a substrate radical to restore it to ita original state. This process is usually known as repair. d) A fourth approach is to form a •complex• between the protector and the moeities in the target compound which are particularly sensitive to irradiation. The complex may be unreacj1ve towards radicals or it may facilitate energy or charge transfer away from the target compound. Protection will be treated mathematically in Section 1.4. In order to reduce anomalous effects from the term­ inal residues during the experimental irradiation of peptides, it is advisable to work with polypeptides. In this project, radiation-induced alteration in the activity of an enzyae waa used aa a sensitive measure of the effects of radiation on a polypeptide. Kost preTious work on the irradiation of enz111es has been perfol"lled on their dilute aqueous solutiona2• How­ ever enzyaea in Nature, exist both in solution (often oxygenated) and bound to insoluble cell components8• Therefore, in the present study the radiation chemistry and protection of an enzyae both in oxygenated aqueous solution and suspension was investigated. The enzyae, oatalase (H2o2 : H2o2 oxidoreductase 1.11.1.6), was chosen aa it is very widely distributed biologically and because an appreciable amount is known about its general properties. (The aias of the project are des­ cribed more completely in Section 1.7). 1.2 RilIATI0I CHllfISTRY 0~ WATER The radiation chemistry of water baa been Tery intensively studied since the mid 1940 1 s and baa been 9-12 reviewed several tiaea • When pure water is irradiated with 60co y-rays (aean photon energy 1.25 KeV.) the energy is primarily absorbed by Compton scattering and as a result the water is exposed to a flux of very fast recoil electrons13: + •- These initial Compton recoil electrons, as well as second­ ary electrons produced by ionization of other water molecules, lose energy and undergo thermalization within 10-13 second of the initial ionization. Following ther­ malization of an electron, adjacent water molecules become polarized and the electron is finally hydrated after about 10-10 second. In accordance with the uncertainty prin­ ciple, the electron is "smeared out• over a large number of water molecules. The formation of the hydrated electron can be represented as e- According to the generally accepted diffusion :model14, the overall effect of this process will be the formation of a track of excited and ionized species 5. along the path ot the Compton recoil electron, with short side-tracks or •spurs•, formed by secondary electrons, being spaced at intervals along the main track. When absorbed in water, sparsely ionizing radiation such as 60co (-rays, give spurs ot about 201 initial diameter and about 104 1 apart15 • An appreciable traction ot the ettects ot such radiation can be attributed to reactions between intact solvent molecules and active species which have diffused from the spur into the bulk ot the solution. The species initially formed on radiolysis, H2o: and e;q initiate a complex series ot reactions, the most important of which are shown below: Ho+ + 2 + H2o ~H30. •aq- + OH• ~011 Ho+l . + 011 ~ 2H20 Ho+ 3 ' + •;q ~H• a· + oH· ~H2o H• + - 8 aq ~H2 + 011 H• + H• ~H2 •aq + e;q ~H2 + 2011 oa· + oa· ~H2o2 6. OH- eaq- + H2o 2 -+OH• + OH• Ho• + H2O2 >H2o + 2 oa· + H2 ► H2o + H• Kost of these reactions are extremely fast (See Appendix 2), the rate constants being of the order of 109 - 1011 •-l seo-1 • In a f-irradiated closed system containing pure water these •products• will destroy each other in such a way that no net chemical change will be detected12• 1.3 BADIA.TIO! CHEMISTRY 01 ~QUEOUS SOLUTIONS Published work in this field demonstrates two main lines of research16•17• Some workers have attempted to explain radiation effects by working baok from the G values (i.e. yields per 100 ev. of energy absorbed) of the final producta17• Others, relying usually on pulse radiolytic experiments, have investigated the initial attack of radicals on various substratea16• Relatively little has yet been achieved in the study of the many secondary reactions which occur after initial attack and ultimately lead to the final products. An attempt has been made to interpret the results of the present study in terms of initial attack by radiation-produced oH• radicals.
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