The Porphyrins V6

Biochemistry, Part A

1st Edition - September 28, 1979
Editor: David Dolphin
Language: English
eBook ISBN:
9 7 8 - 0 - 3 2 3 - 1 4 1 9 4 - 9

The Porphyrins, Volume VI: Biochemistry, Part A deals with the biochemistry of porphyrins, their precursors, catabolic derivatives, and related compounds. The book covers the… Read more

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The Porphyrins, Volume VI: Biochemistry, Part A deals with the biochemistry of porphyrins, their precursors, catabolic derivatives, and related compounds. The book covers the biosynthesis of porphyrins and chlorophylls; the formation and metabolism of bile pigments in animals and plants; as well as the synthesis, characterization, and chemistry of the bile pigments and their derivatives. An account of the historical and clinical aspects of porphyrins and bile pigments is also given. This volume is organized into 12 chapters and begins with an overview of protoporphyrins and their metabolic intermediates, paying particular attention to their synthesis and biosynthesis. The discussion then shifts to the biosynthesis of porphyrins and chlorophylls; the in vivo formation and metabolism of bile pigments such as biliverdin and bilirubin; and yellow, green, and blue bile pigments. The reader is then introduced to bile pigments of plants including phytochrome and phycobiliproteins; the general structures and nomenclature of bile pigment derivatives; and the Stokvis reaction. The book also considers the clinical chemistry of porphyrins, and then concludes with a chapter on milestones in the history of bile pigments. This book will be of value to inorganic, organic, physical, and biochemists interested in the biochemistry of porphyrins.

List of Contributors

General Preface

Preface

Contents of Other Volumes

1 Protoporphyrin: Synthesis and Biosynthesis of Its Metabolic Intermediates

I. S-Succinyl-Coenzyme A

II. 5-Aminolevulinic Acid

III. Porphobilinogen

IV. Uroporphyrinogens, Coproporphyrinogens, Protoporphyrin, and Cobyrinic Acid

References

2 Biosynthesis of Porphyrins

I. Introduction

II. Enzymatic Synthesis of δ-Aminolevulinic Acid

III. Enzymatic Synthesis of Porphobilinogen: ALA Dehydratase

IV. Tetrapyrrole Biosynthesis

V. Biosynthesis of Coproporphyrinogens

VI. Formation of Protoporphyrinogen by the Oxidative Decarboxylation of Coproporphyrinogen III

VII. Enzymatic Conversion of Protoporphyrinogen to Protoporphyrin

VIII. Formation of Iron Protoporphyrin

IX. Control of Porphyrin Biosynthesis

References

3 Chlorophyll Biosynthesis

I. Introduction

II. Pathway to Chlorophyll a

III. Biosynthesis of Chlorophyll b

IV. Pathway to Bacteriochlorophyll a

V. Biosynthesis of Other Chlorophylls

References

4 Enzymatic Synthesis of Porphyrins

I. Introduction

II. δ-Aminolevulinic Acid

III. Porphobilinogen

IV. Porphyrinogens

V. Uroporphyrin I

VI.Uroporphyrin III

VII. Porphyrins with Seven, Six, and Five Carboxyl Groups

VIII. Coproporphyrin I

IX. Coproporphyrin III

X. Protoporphyrin

XI. General Methods

XII. Conclusion

References

5 Formation and Metabolism of Bile Pigments in Vivo

I. General Aspects

II. Formation of Biliverdin

III. Reduction of Biliverdin to Bilirubin

IV. Conjugation and Biliary Excretion of Bilirubin

V. Appendix

References

6 Bile Pigments: Bilatrienes and 5,15-Biladienes

I. Introduction

II. Preparation and Isolation

III. General Properties

IV. Chemical Reactions

V. Biological Aspects

VI. Spectra

VII. Practical Aspects

VIII. Appendix

References

7 Bile Pigments of Plants

I. Introduction

II. Phytochrome

III. Phycobiliproteins

References

8 Derivatives of Bile Pigments

I. Introduction

II. General Structures and Nomenclature

III. Biogenesis

IV. Reactions Revealing Structure

V. Stereochemistry through Optical Rotatory Dispersion and Circular Dichroism

VI. The Compounds

References

9 Synthesis, Purification, and Characterization of Bile Pigments and Related Compounds

I. Introduction

II. Building Blocks for the Synthesis of Bile Pigments

III. Bilinediones

IV. Biladienediones

V. Bilene-a-diones: Dihydrobilirubins (1,10,15,16,19,21,23,24-Octahydro-1,19-dioxo-22H-bilins)

VI. Bilene-b-diones

VII. Bilanediones

VIII. Chemical Characterization of Bile Pigments

IX. Polarographic Studies

References

10 The Stokvis Reaction

I. History, Occurrence, and Nomenclature

II. Technique of the Stokvis Reaction

III. Propentdyopents: Source, Structure, and Synthesis

IV. Structure of Propentdyopent Adducts

V. Properties of Propentdyopents and Their Adducts

VI. Structure of Pentdyopent and the Course of the Stokvis Reaction

VII. The Fecal Pigment

References

11 Clinical Chemistry of the Porphyrins

I. Introduction

II. Chemistry of Clinically Important Porphyrins

III. Heme Biosynthetic Pathway

IV. Evaluation of Porphyrin Metabolism in Health and Disease

V. Survey of Available Methods of Porphyrin Analysis in Excreta, Blood, and Tissues

VI. Values in Normal Subjects and Patients with Nonporphyric Disorders

VII. Classification of Human Porphyric Disorders

VIII. Simple Screening Tests and "Simplified" Screening Procedures

IX. Clinical Manifestations of Porphyrias

X. Biochemical Findings in Porphyric Disorders

XI. Biochemistry of the Acute Attack—Porphyrin Precursors in the Pathogenesis of the Acute Attack

XII. Applications of Thin-Layer Chromatographic Analysis in the Clinical Investigation of Porphyrias

XIII. Porphyrin Biosynthetic Enzyme Activities of the Human Porphyrias

Appendix I. Solvents and Standard Reference Porphyrins

Appendix II. Routine Quantative Methods

Appendix III. Special Techniques

Appendix IV. Advanced Analytical Techniques

Appendix V. Other Ancillary Methods of Structural Analysis

References

12 Historical and Clinical Aspects of Bile Pigments

I. Milestones in the History of Bile Pigments

II. Bilirubin Metabolism—Clinical Aspects

III. Methods

References

Author Index

Subject Index