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Chemical Pathways of Metabolism PDF

395 Pages·2014·24.853 MB·English
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CHEMICAL PATHWAYS OF METABOLISM VOLUME II This page intentionally left blank Chemical Pathways of Metabolism EDITED BY DAVID M. GREENBERG Department of Physiological Chemistry School of Medicine University of California Berkeley, California VOLUME II 1954 ACADEMIC PRESS INC., PUBLISHERS NEW YORK, N. Y. Copyright 1954, by ACADEMIC PRESS INC. 125 EAST 23RD STREET NEW YORK 10, N.Y. All Rights Reserved No part of this book may be reproduced in any form, by photostat, microfilm, or by any other means, without written permission from the publishers. Library of Congress Catalog Card Number: 54-7613 PRINTED IN THE UNITED STATES OF AMERICA CONTRIBUTORS TO VOLUME II H. BORSOOK, Kerckhoff Laboratories of Biology, California Institute of Technology, Pasadena, California P. P. COHEN, Department of Physiological Chemistry, University of Wisconsin, Madison, Wisconsin S. GRANICK, Rockefeller Institute for Medical Research, New York, New York D. M. GREENBERG, Department of Physiological Chemistry, School of Medicine, University of California, Berkeley, California LEON A. HEPPEL, National Institutes of Health, U. S. Public Health Service, Bethesda, Maryland MARTIN P. SCHULMAN, Department of Biochemistry, State University of New York Medical School, Syracuse, New York V This page intentionally left blank CONTENTS CONTRIBUTORS TO VOLUME II v LIST OF ABBREVIATIONS AND SYMBOLS ix CONTENTS OF VOLUME I x 9. Nitrogen Metabolism of Amino Acids BY P. P COHEN 1 I. Scope 1 II. Deamination 1 III. Deamidation 26 IV. Transamination 29 V. Amino Acid Racemases 36 VI. Urea Synthesis 36 VII. Summary Remarks 43 Addendum 45 10. Carbon Catabolism of Amino Acids BY DAVID M. GREENBERG 47 I. Scope of the Chapter 48 II. Amino Acids Linked with the Citric Acid Cycle 49 III. Glycine 52 IV. The /3-Hydroxyamino Acids 54 V. The Aliphatic Branched-Chain Amino Acids 59 VI. Certain Amino Acids of Uncertain Biological Significance 70 VII. The Sulfur Amino Acids 72 VIII. Lysine 76 IX. Arginine and Ornithine 79 X. Proline and Hydroxyproline 80 XL The Aromatic Amino Acids 80 XII. Tryptophan 90 XIII. Histidine 101 Addenda Ill 11. Synthetic Processes Involving Amino Acids BY DAVID M. GREENBERG . .. 113 I. Introduction 113 II. The Glycine-Serine Interconversion 114 III. Formation of Phosphatide Bases 116 IV. Interconversions of Glutamic Acid, Ornithine, and Proline 123 V. Biosynthesis of Branched-Chain Amino Acids 127 VI. Lysine Biosynthesis 130 VII. Biosynthesis of Aromatic Amino Acids 131 VIII. Reactions Involving Tyrosine 134 IX. Synthetic Reactions Involving Tryptophan 138 X. Biosynthesis of Histidine 145 Addenda 147 vii Vlll CONTENTS 12. Metabolism of Sulfur-Containing Compounds BY DAVID M. GREENBERG . . 149 I. Biologically Important Sulfur Compounds 149 II. Relationships of Methionine and Cysteine 151 III. Oxidation of Sulfur-Containing Amino Acids 155 IV. The Desulfhydrase Reaction 162 V. Thiosulfate and Thiocyanate 163 VI. Reactions of Sulfur-Containing Coenzymes 163 13. Enzymatic Syntheses of Peptide Bonds BY H. BORSOOK 173 I. Thermodynamic Considerations 174 II. Classification of Enzymatic Peptide Syntheses According to the Sign and Magnitude of the Free Energy Change (— AF) 182 III. Peptide Syntheses Where — AF Is Negative and Large: Coupled with High-Energy Phosphate 198 IV. Mechanism of Amino Acid Incorporation into Proteins 203 V. Addendum (David M. Greenberg) 219 14. Purines and Pyrimidines BY MARTIN P. SCHULMAN 223 I. The Purines 224 II. The Pyrimidines 248 15. Nucleotides and Nucleosides BY LEON A. HEPPEL 263 I. Nucleosides 264 II. Nucleotides 270 III. Deamination of Nucleosides and Nucleotides 277 IV. The Enzymatic Splitting of Certain Coenzyme Nucleotides 279 V. The Enzymatic Synthesis of Certain Coenzyme Nucleotides 280 16. Metabolism of Heme and Chlorophyll BY S. GRANICK 287 I. Introduction 288 II. Compounds of the Biosynthetic Chain Leading to the Formation of Protoporphyrin 295 III. Biochemical Lesions in the Porphyrin Metabolism of Human Beings. . 308 IV. Tracer Studies of Protoporphyrin Biosynthesis 311 V. The Iron Branch of the Biosynthetic Chain and Some General Proper­ ties of Heme Compounds 319 VI. The Magnesium Branch and the Biosynthesis of Chlorophyll 329 VII. Decomposition of Iron Protoporphyrin to Bile Pigments 331 AUTHOR INDEX 343 SUBJECT INDEX 359 ERRATA: VOLUME I 384 LIST OF ABBREVIATIONS AND SYMBOLS AMP adenosine-5-phosphate ADP adenosine diphosphate ATP adenosine triphosphate DPN , DPN+, DPN diphosphopyridine nucleotide (cozy- OI mase, coenzyme I) DPN , DPNH reduced form of above red TPN , TPN+ TPN , TPNH triphosphopyridine nucleotide (coen­ OI red zyme II) FAD flavin adenine dinucleotide CoA, CoASH coenzyme A RSH sulfhydryl compounds SH S / /I L ,L lipoic acid, thioctic acid \ \ SH S Kcal. kilocalories Kj. kilojoules metabolic quotients expressed in μΐ. 'ΐθ2? Vacetatej ClC. metabolite/mg. dry weight/hr. AF increment of free energy AF° standard free energy change RNA ribose nucleic acid PNA pentose nucleic acid, desoxyribose nu­ cleic acid Pi inorganic phosphate PPi inorganic pyrophosphate PPPi inorganic triphosphate

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