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69-22,134 GOSSER, Leo Anthony, 1942- an EQUILIBRIUM AND This dissertation has been microfilmed exactly as received 69-22,134 GOSSER, Leo Anthony, 1942- AN EQUILIBRIUM AND REACTION STUDY OF THE GLYCYLGLYCINATE - GLYOXALATE NICKEL(II) AND ZINC(II) SYSTEMS. The Ohio State University, Ph.D., 1969 Chemistry, analytical University Microfilms, Inc., Ann Arbor, Michigan AM EQUILIBRIUM AND REACTION STUDY OF THE GLYCYLGLYCINATE - GLYOXALATE - NICKEL(II) AND ZINC(II) SYSTEMS DISSERTATION Presented In Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy in the Graduate School of The Ohio State University By Leo Anthony Gossor, 3«S. The Ohio State University 3.969 Approved by Adviser epartment of Che ACKNOWLEDGMENTS The author wishes to express his appreciation to Dr. Daniel L.Leusslng for his encouragement and advice during the course of this work. Financial aid from the Ohio State University in the form of both research and teaching assistantshlps, from the National Science Foundation for a Summer Fellowship, and from National Defense loans Is'gratefully acknowledged. I am especial­ ly grateful to my wife, Mary Louise, for her continuous patience and assistance in the preparation of this dissertation. This work is dedicated to my parents in appreciation for their gifts of faith and love. ii VITA May 30, 1942. Born - Shelby, Ohio 1964.......... B.S., St. Vincent College, Latrobe, Pennsylvania 1964-1966 .... Teaching Assistant, Department of Chemistry, The Ohio State University, Columbus, Ohio Summer of 1966. National Science Foundation Summer Fellow, Department of Chemistry, The Ohio State University, Columbus, Ohio 1966-1969 .... Research AssistantDepartment of Chemistry, ThtkOhio .State.‘Uniy.prtsity, Columbus, Ohio '■ ':■■■■■ *..1 ’■ . ; t i , 1969.......... Scifcnt.ist-,,.Scifcnt.is ty. War^'ejr/iliainhjert h\ir,rier>hlambjfir 'Research c ■'K.es eari institute, •• Morria \?icihs/':NewvrjV:rstty • ' • *. •. 'I . > * I PUBLICATIONS . None FIELDS OF STUDY Major Field: Chemistry ill TABLE OF CONTENTS ACKNOWLEDGMENTS VITA........... TABLE OF CONTENTS LIST OF TABLES LIST OF FIGURES . Chapter I. INTRODUCTION A. Schiff Base Systems........................ B. Determination of Equilibrium Constants . C. Glycylglycine-Glyoxalate Mixed Syste\n , . , . D. Statement of the Problem ................... II. EXPERIMENTAL A. Reagents B. Procedure III. NUMERICAL TREATMENT ................. , IV. RESULTS AND DISCUSSION A. Glycylglycine and Its Metal Complexes B. Schiff Base and Mixed Systems. C. Schiff Base Reactions. D. Summary of Results . ......... APPENDIX A. DATA APPENDIX B. FRACTION PLOTS LIST OF REFERENCES LIST OF TABLES. Table 0 Page .1. pK^ Values Reported for Glycylglycine; ................. kO 2 * PK0cl Values of Glycylglycine and Related Compounds. • UO 3. Formation Constants for Glycylglycine................... 1»8 * It. Near-IR and Visible Spectra............................. 30 5 1 Amide Dissociation Constants..................... 32 6. Schiff Base Formation Constants......................... 33 7* Formation Constants for Glycylglycine-Glyoxalate . 62 6. LEF V a l u e s ............................. 67 9# Carbon Dioxide Evolution.......................... 86 10. Equilibrium Constants for Glycine........ ' ......... 112 v LIST OF FIGURES Figure 0 Page 1, Reactions of the Pyridoxal Schiff Base Metal Complex................. 2 2, Mechanism of Pyridoxal Schiff Base Reactions... It 3, Structures of Schiff Base Complexes ................ 7 1*. Electron Mobility in Aldehydes, ........ 8 5. Titration Curve of Glycylglycine with H C 1 .......... 35 6. Titration Curve of Glycylglycine with NaOH.......... 37 7# Formation Curve of Glycylglycine.................... 39 8. Titration of Hi(ll)-Glycylglycine .................. U3 9. Titration of Zn{ll)-Glycylglycine .................. U5 10. Formation Curves of Glycylglycine-Metal Complexes . 1*7 11, Titration of Glycylglycine-Glyoxalate .............. 55 12, Change in pH with Time for Addition of Glyoxalate to Glycylglycine-Metal Solutions. .......... 58 13. Change in pH for Addition of Glyoxalate to Hi(ll)-Glycylglycinate Solutions.............. 60 lU. Stepwise Formation Constants in Ni(II)-Mixed System............... 6h 15.' Stepwise Formation Constants in Zn(II)-Mixed System.................. 66 16 . HMR Spectrum of Glycylglycine-Glyoxalate at 25°C. • 71 17. NMR Spectrum of Glycylglycine-Glyoxalate at 0°C .. 73 vi ■ LIST OF FIGURES (cont.) Figure if Page L8. UV Spectra of Glycinate-GIyoxalate ......... 7T 19. Trans aminated Schiff Base. ......... • T • . 78 20. UV Spectra of Glycylglycinate-Glyoxalate.............. 80 21. UV Spectra of Glycylglycinate-Glyoxalate.............. 8 3 22. Effect of Zn(ll) on the UV Spectra of Glycinate-GIyoxalate.................... • • • 88 23. Effect of Zn(ll) on the UV Spectra of Glycylglycinate-Glyoxalate ...••• ........... 90 2l», Effect of Hi(ll) on the UV Spectra of Glycylglycinate-Glyoxalate ........... ...... 93 25, NMR Chemical Shift as a Function of n for Glycine. ......................... 96 26, HMR Chemical Shift as a Function of By for Glycylglycine........................... 98 27, HMR Spectra of Glycylglycinate-Zn(ll). .......... 100 28, HMR Spectra of Glycylglycinate-Glyoxalate.......... 103 29* HI© Spectra of Glycylglycinate-Glyoxalate.......... 106 30. HMR Spectra of Glycylglyclnate-Glyoxalate-Zn(ll) . • 109 31. HMR Spectrum of Glycinate-GIyoxalate . .......... Ill vii I. INTRODUCTION Much attention has been given in recent years to the investiga­ tion of model enzymatic systems. It ‘is hoped that a better under­ standing of biological processes will develop from this work on model systems. Already significant advances have been made in the elucidation of the mechanisms by which some of the more common enzymes function. An example of the progress toward an understand­ ing of enzymatic reactions is the recently completed work of Dunathan 1 2 et al. * on the stereochemistry of enzymatic transaminations. Progress along these lines is dependent upon the knowledge of funda­ mental chemical reactions. A basic quantitative understanding of model systems is, therefore, of paramount importance in the applica­ tion of these systems to their more complex enzymatic counterparts. A. Schiff Base Systems As a result of their role in transamination reactions, Schiff bases and Schiff base-metal complexes have been the object of con­ siderable interest in the model enzymatic systems. In addition,to their function as intermediates in transamination reactions, Schiff bases have also been investigated as activated intermediates for decar­ boxylations, trans-iminations, the reversible cleavage of /3 -hydroxy- 3 amino acids, deaminations and racemizations. Metzler and Snell have contributed a wealth of information concerning the pyridoxal systems. 1 Pyridoxal is of great interest as the vitamin cofactor of enzymatic transamination reactions. From a series of work, on pyridoxal, Metzler Ikawa and Snell^ have proposed a general mechanism in which the pyri­ doxal forms a Schiff base Intermediate. In non-enzymatic systems the Schiff base is bound to a metal ion, whereas, in enzymatic systems there is probably not a metal complex. The following mechanism ex­ plains the role of pyridoxal in a variety of reactions. Figure 1 shows the structure of the proposed intermediate. It can be seen that this form of intermediate may lead to different types of reactions, depending upon which bond to the amino acid carbon atom is most easily fractured. H FRACTURE OF PRODUCES I* .0 R — C -Z-C? Bond 1 Cleavage reactions 0 Bond 2 Carbanion formation H-C Bond 3 Decarboxylation h o h £c Pyridoxal Intermediate Figure 1. Reactions of the Pyridoxal Schiff Base Metal Complex Figure 2 Illustrates the mechanism for transamination and racem- Ization. The components of the pyridoxal system which are essential 4 for Its catalytic properties are the formyl and phenolic groups in the proper orientation and the pyridinium ring. Work with compounds structurally similar to pyridoxal has in­ creased the scope of systems which may be applicable as model enzymat­ ic systems. Ikawa and Snell** found that 4-nitrosalicylaldehyde in the presence of metals possesses some of the catalytic activity of Its pyridoxal analog. The dehydration of serine, the splitting of threo­ nine to glycine, and the desulfhydration of cysteine are promoted by 4-nitrosalicylaldehyde through the same type of Schiff base intermed­ iate as that of pyridoxal. This work along with investigations on other salicylaldehyde compounds has shown that nearly all pyridoxal- catalyzed reactions can be catalyzed by other compounds albeit perhaps not as effectively as pyridoxal. Harada and Oh-hashi^ have studied the condensation reactions of carbonyl compounds with the N-salicylideneglycinatocopper(II) complex. Under moderate conditions (pH = 7-8, 25 - 1°C, 24 hours in an aqueous solution), they have reported over 80^.' yield of threonine by the con­ densation of acetaldehyde with glycine. Likewise lesser yields of phenylserine, /3 -hydroxyaspartlc acid, and serine were formed by the condensation of benzaldehyde, glyoxyllc acid and formaldehyde respect­ ively with the glycine Schiff base complex. The formation of /3 -hydroxyamino acids as promoted by salicylaldehyde and copper(II) is shown in the following scheme. u 9 HOHjC N v i ^ C H , H* Pyridoxal Intermediate I-H+ R - ^ - c f 0 H-C HOH?C R I R-C-COO' H*- ac-C O O II HOHjC HOH,C N CH hydrolysis hydrolysis Racemization Transamination Figure 2. Mechanism of Pyridoxal Schiff Base Reactions 5 ? " f - . 0 pH T-8 +RCHO > H20 25°C The similarities
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