Biosynthesis of tetrapyrroles

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Veröffentlicht: Amsterdam [u.a.] Elsevier 1991
Schriftenreihe:New comprehensive biochemistry 19
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245 1 0 |a Biosynthesis of tetrapyrroles  |c ed. P. M. Jordan 
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adam_text IMAGE 1 VLL CONTENTS FOREWORD V CHAPTER 1 THE BIOSYNTHESIS OF 5-AMINOLAEVULNIC ACID AND ITS TRANSFORMATION INTO UROPORPHY- RINOGEN III P.M. JORDAN (LONDON, UK) 1 1. INTRODUCTION 1 2. EARLY ISOTOPIC STUDIES ON THE ORIGIN OF THE TETRAPYRROLE RING 2 3. THE BIOSYNTHESIS OF 5-AMINOLAEVULINIC ACID FROM GLYCINE 4 3.1. OCCURRENCE AND PROPERTIES OF 5-AMINOLAEVULINIC ACID SYNTHASE 4 3.2. REGULATION OF 5-AMINOLAEVULINIC ACID SYNTHASE IN BACTERIA 5 3.3. REGULATION OF 5-AMINOLAEVULINIC ACID SYNTHASE IN EUKARYOTES 6 3.4. SUBSTRATE SPECIFICITY AND KINETICS 9 3.5. MECHANISM OF 5-AMINOLAEVULINIC ACID SYNTHASE 11 3.6. STRUCTURE OF THE ENZYME AND MOLECULAR BIOLOGY 14 4 THE BIOSYNTHESIS OF 5-AMINOLAEVULINIC ACID FROM GLUTAMATE 15 4.1. DISCOVERY OF THE C-5 PATHWAY 15 4.2. THE ENZYMES OF THE C-5 PATHWAY 16 5. THE BIOSYNTHESIS OF PORPHOBILINOGCN 19 5.1. INTRODUCTION 19 5.2. GENERAL PROPERTIES OF 5-AMINOLAEVULINIC ACID DEHYDRATASES 20 5.3. IMPORTANCE OF SULFHYDRYL GROUPS 21 5.4. REQUIREMENT FOR METALS 22 5.5. INHIBITION BY LEAD 23 5.6. NATURE OF THE ACTIVE SITE GROUPS 24 5.7. ORDER OF BINDING THE TWO SUBSTRATES AND THE ENZYME MECHANISM 26 5.8. CATALYTIC GROUPS AND THE NATURE OF THE ACTIVE SITE 28 6. THE BIOSYNTHESIS OF UROPORPHYRINOGEN III 30 6.1. INTRODUCTION 30 6.2. PROPERTIES OF PORPHOBILINOGEN AND UROPORPHYRINOGENS 32 6.3. PORPHOBILINOGEN DEAMINASE 33 6.4. UROPORPHYRINOGEN III SYNTHASE (COSYNTHASE) 34 6.5. EARLY INVESTIGATIONS ON THE MECHANISM OF UROPORPHYRINOGEN BIOSYNTHESIS 34 6.6. EXPERIMENTS WITH AMINOMETHYLDIPYRROMETHANES, AMINOMETHYLTRIPYRRANES AND AMINO- METHYLBILANES 35 6.7. THE DISCOVERY OF PREUROPORPHYRINOGEN, THE SUBSTRATE FOR UROPORPHYRINOGEN III SYNTHASE 38 6.8. ORDER OF ASSEMBLY OF THE FOUR PYRROLE RINGS OF THE TETRAPYRROLE 41 6.9. ENZYME INTERMEDIATE COMPLEXES BETWEEN THE DEAMINASE AND PORPHOBILINOGEN 42 6.10. PRELIMINARY STUDIES ON THE NATURE OF THE ENZYMIC GROUP INVOLVED IN SUBSTRATE COVALCNT BINDING 43 6.11. DISCOVERY OF A COFACTOR IN ALL PORPHOBILINOGEN DEAMINASES -THE DIPYRROMETHANE COFACTOR 43 6.12. FURTHER EVIDENCE FOR THE ROLE OF THE DIPYRROMETHANE COFACTOR FROM EXPERIMENTS WITH THE CHAIN TERMINATION SUICIDE INHIBITOR A-BROMOPORPHOBILINOGEN 46 6.13. ATTACHMENT SITE AND MECHANISM OF ASSEMBLY OF THE DIPYRROMETHANE COFACTOR 47 IMAGE 2 VLLL 6.14. MECHANISM OF ACTION OF PORPHOBILINOGEN DEAMINASE 49 6.15. REACTION OF PORPHOBILINOGEN DEAMINASE WITH 1-AMINOMETHYLBILANES 53 6.16. STERIC COURSE OF THE PORPHOBILINOGEN DEAMINASE AND UROPORPHYRINOGEN III SYNTHASE REACTIONS 53 6.17. USE OF SYNTHETIC ANALOGUES TO INVESTIGATE THE UROPORPHYRINOGEN III SYNTHASE REACTION . 55 6.18. MECHANISM OF ACTION OF UROPORPHYRINOGEN III SYNTHASE 56 6.19. MOLECULAR BIOLOGY AND PROTEIN STRUCTURE OF PORPHOBILINOGEN DEAMINASE 57 6.20. MOLECULAR BIOLOGY OF UROPORPHYRINOGEN SYNTHASE 58 ACKNOWLEDGEMENTS 59 REFERENCES 59 CHAPTER 2 MECHANISM AND STEROCHEMISTRY OF THE ENZYMES INVOLVED IN THE CONVERSION OF URO- PORPHYRINOGEN III INTO HAEM M. AKHTAR (SOUTHAMPTON, HANTS., UK) 67 1. INTRODUCTION 67 2. UROPORPHYRINOGEN DECARBOXYLASE (UROPORPHYRINOGEN CARBOXYLYASE) 67 2.1. INTRODUCTION 67 2.2. INTERMEDIATES IN THE DECARBOXYLATION 68 2.3. THE INTERACTION BETWEEN THE DECARBOXYLASE AND THE SUBSTRATES 70 2.4. ISOLATION AND STRUCTURAL STUDIES ON UROPORPHYRINOGEN DECARBOXYLASE 72 2.5. THE NUMBER OF ACTIVE SITES 73 2.6. MECHANISTIC AND STEREOCHEMICAL STUDIES 74 2.7. THE MECHANISM 75 3. COPROPORPHYRINOGEN III OXIDASE 77 3.1. INTRODUCTION 77 3.2. ISOLATION OF, AND STRUCTURAL STUDIES ON, COPROPORPHYRINOGEN OXIDASE 78 3.3. THE ORDER IN WHICH THE PROPIONIC SIDE-CHAINS ARE DECARBOXYLATED 79 3.4. STEREOCHEMICAL AND MECHANISTIC STUDIES ON COPROPORPHYRINOGEN III OXIDASE 79 3.5. THE MECHANISM OF THE AEROBIC COPROPORPHYRINOGEN III OXIDASE CATALYSED REACTION . . .. 81 3.6. CONCERNING THE STEREOCHEMISTRY AND MECHANISM OF THE ANAEROBIC COPROPORPHYRINOGEN III OXIDASE 83 4. PROTOPORPHYRINOGEN IX OXIDASE 84 4.1. INTRODUCTION 84 4.2. ISOLATION OF, AND STRUCTURAL STUDIES ON, PROTOPORPHYRINOGEN IX OXIDASE 85 4.3. STEREOCHEMICAL AND MECHANISTIC STUDIES ON PROTOPORPHYRINOGEN IX OXIDASE 86 4.4. THE MECHANISM OF THE PROTOPORPHYRINOGEN IX OXIDASE CATALYSED REACTION 90 5. FERROCHELATASE 92 5.1. OCCURRENCE AND ISOLATION OF FERROCHELATASES 92 5.2. PROPERTIES OF FERROCHELATASES 92 5.3. SUBSTRATE SPECIFICITY 93 5.4. METAL REQUIREMENTS 94 5.5. INHIBITION OF FERROCHELATASES BY N-ALKYLPORPHYRINS 94 5.6. KINETICS, ACTIVE SITE AND MECHANISM OF ACTION OF FERROCHELATASES 95 ACKNOWLEDGEMENTS 96 REFERENCES 96 IMAGE 3 IX CHAPTER 3 THE BIOSYNTHESIS OF VITAMIN B, 2 A.I. SCOTT AND P.J. SANTANDER (COLLEGE STATION, TX, USA) 101 1. INTRODUCTION 101 2. THE CARBON BALANCE 104 3. STEREOCHEMISTRY OF METHYL GROUP INSERTION IN CORRINOID BIOSYNTHESIS 104 4. CONCERNING THE FATE OF THE METHYL GROUP PROTONS 106 5. URO GEN III IS A PRECURSOR OF VITAMIN B 12 106 6. CHARACTERIZATION AND INTERMEDIACY OF THE ISOBACTERIOCHLORINS OF P. SHERMANII 107 7. THE METHYLATION SEQUENCE: PULSE EXPERIMENTS 112 8. TIMING OF THE DECARBOXYLATION STEP 116 9. THE PROTEIN BALANCE OF VITAMIN B 12 BIOSYNTHESIS 120 10. FACTORS S,-S 4, ISOMERIC, TETRAMETHYLATED CORPHINOIDS DERIVED FROM URO GEN I 123 11. THE METHYL TRANSFERASES 128 12. BIOSYNTHESIS OF THE NEUCLEOTIDE LOOP AND COENZYME B, 2 132 13. EVOLUTIONARY ASPECTS OF B, 2 BIOSYNTHESIS 133 13.1. THE C 5 PATHWAY 133 13.2. CHEMICAL METHODS 134 13.3. WHY TYPE III? 134 REFERENCES 135 CHAPTER 4 BIOCHEMISTRY OF COENZYME F430, A NICKEL PORPHINOID INVOLVED IN METHANOGENESIS H.C. FRIEDMANN, A. KLEIN AND R.K. THAUER (MARBURG, FRG AND CHICAGO, IL, USA) 139 1. INTRODUCTION 139 2. STRUCTURAL RELATIONS TO OTHER TETRAPYRROLES 140 3. BIOSYNTHESIS FROM GLUTAMATE VIA UROPORPHYRINOGEN III AND DIHYDROSIROHYDROCHLORIN 143 4. PROPERTIES OF FREE COENZYME F430 INCLUDING ITS REDOX BEHAVIOUR 144 5. FUNCTION OF COENZYME F430 AS PROSTHETIC GROUP OF METHYL COENZYME M REDUCTASE IN METHANO- GENESIS 147 6. COMPARATIVE ANALYSIS OF GENES ENCODING METHYL COENZYME M REDUCTASE 149 ACKNOWLEDGEMENTS 152 REFERENCES 152 CHAPTER 5 BIOCHEMISTRY AND REGULATION OF PHOTOSYNTHETIC PIGMENT FORMATION IN PLANTS AND ALGAE S.I. BEALE AND J.D. WEINSTEIN (PROVIDENCE, RI AND CLEMSON, SC, USA) . . 155 1. THE VARIETY AND FUNCTIONS OF PLANT AND ALGAL TETRAPYRROLES 155 1.1. INTRODUCTION TO THE BRANCHED TETRAPYRROLE BIOSYNTHETIC PATHWAY 155 1.2. CHLOROPHYLLS AND BACTERIOCHLOROPHYLLS 155 IMAGE 4 1.3. HEMES 1.4. PHYCOBILINS AND THE PHYTOCHROME CHROMOPHORE 1.5. OTHER TETRAPYRROLES FOUND IN PHOTOTROPHIC ORGANISMS . THE BIOSYNTHETIC ROUTE 2.1. ALA FORMATION IMAGE 5 XI 3. REGULATION 202 3.1. ENVIRONMENTAL AND PHYSIOLOGICAL MODULATION OF PIGMENT CONTENT 202 3.1.1. PHYSIOLOGY OF GREENING IN PLANTS AND ALGAE 202 3.1.2. EFFECTS OF FE CHELATORS AND ANAEROBIOSIS ON GREENING IN INTACT TISSUE AND CHLOROPLASTS 205 3.1.3. CHLOROPHYLL AND HEME TURNOVER 206 3.1.4. NONPLASTID HEME SYNTHESIS AND TURNOVER 208 3.2. REGULATION OF BIOSYNTHETIC STEPS 209 3.2.1. SUBCELLULAR COMPARTMENTATION OF TETRAPYRROLE BIOSYNTHESIS 209 3.2.2. REGULATIONS OF METABOLIC ACTIVITY 210 3.2.2.1. EFFECTOR-MEDIATED REGULATION OF ALA-FORMING ACTIVITY 211 3.2.2.2. EXPRESSION AND TURNOVER OF ALA-FORMING ENZYMES 213 3.2.2.3. REGULATION OF ALA DEHYDRATASE ACTIVITY 215 3.2.2.4. BRANCH POINT REGULATION 215 3.2.2.5. REGULATION OF PROTOCHLOROPHYLLIDE PHOTOREDUCTION 216 3.3. REGULATION OF PHYCOBITIN CONTENT BY LIGHT AND NUTRITIONAL STATUS 218 3.3.1. LIGHT EFFECTS 218 3.3.2. RESPONSES TO NITROGEN STATUS 221 ACKNOWLEDGMENTS 222 REFERENCES 223 CHAPTER 6 THE STRUCTURE AND BIOSYNTHESIS OF BACTERIOCHLOROPHYLLS KEVIN M. SMITH (DAVIS, CA, USA) 237 1. NOMENCLATURE 237 2. OCCURRENCE AND STRUCTURES 238 2.1. BACTERIOCHLOROPHYLLS A, B 238 2.2. BACTERIOCHLOROPHYLLS C, D, E,F 239 2.3. BACTERIOCHLOROPHYLL G 239 3. BIOSYNTHESIS 240 3.1. BACTERIOCHLOROPHYLLS A, B, G 240 3.2. BACTERIOCHLOROPHYLLS E, D, E,F 246 ACKNOWLEDGMENT 253 REFERENCES 253 CHAPTER 7 THE GENES OF TETRAPYRROLE BIOSYNTHESIS P.M. JORDAN AND B.I.A. MGBEJE (LONDON, UK) 257 1. GENES OF HAEM BIOSYNTHESIS 257 1.1. MAPPING OF HAEM BIOSYNTHESIS GENES 257 1.1. THE HEM GENES IN ESCHERICHIA COLI 258 1.2. THE HEM GENES IN SALMONELLA TYPHIMURIUM 259 1.3. THE HEM GENES IN STAPHYLOCOCCUS AUREUS 260 1.4. THE HEM GENES IN BACILLUS SUBTILIS 260 1.5. THE HEM GENES IN RHODOBACTER SPHAEROIDES 261 1.6. THE HEM GENES IN YEAST 261 IMAGE 6 XLL 1.1.7. THE HEM GENES IN MAMMALIAN SPECIES 262 1.2. MOLECULAR BIOLOGY OF HAEM BIOSYNTHESIS GENES 263 1.2.1. 5-AMINOLAEVULINIC ACID SYNTHESIS 263 1.2.1.1. 5-AMINOLAEVULINIC ACID SYNTHASE (THE GLYCINE PATHWAY) 263 1.2.1.2. THE GENES OF THE GLUTAMATE (C 5) PATHWAY 266 1.2.2. 5-AMINOLAEVULINIC ACID DEHYDRATASE 268 1.2.3. PORPHOBILINOGEN DEAMINASE 269 1.2.4. UROPORPHYRINOGEN III SYNTHASE (COSYNTHASE) 272 1.2.5. UROPORPHYRINOGEN DECARBOXYLASE 273 1.2.6. COPROPORPHYRINOGEN OXIDASE 274 1.2.7. PROTOPORPHYRINOGEN OXIDASE 275 1.2.8. FERROCHELATASE 275 2. GENES OF COBALAMIN (VITAMIN B L2) BIOSYNTHESIS 276 3. GENES OF BACTERIOCHLOROPHYLL AND CHLOROPHYLL BIOSYNTHESIS 282 3.1. BACTERIOCHLOROPHYLL BIOSYNTHESIS GENES 282 3.2. CHLOROPHYLL BIOSYNTHESIS GENES 287 REFERENCES 288 SUBJECT INDEX 295
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illustrated Illustrated
indexdate 2024-12-23T11:22:14Z
institution BVB
isbn 0444892850
language English
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physical XII, 309 S. graph. Darst.
publishDate 1991
publishDateSearch 1991
publishDateSort 1991
publisher Elsevier
record_format marc
series New comprehensive biochemistry
series2 New comprehensive biochemistry
spellingShingle Biosynthesis of tetrapyrroles
New comprehensive biochemistry
Pyrroles metabolism
Tetrapyrroles Synthesis
Pflanzen (DE-588)4045539-7 gnd
Stoffwechsel (DE-588)4057699-1 gnd
Tetrapyrrole (DE-588)4140190-6 gnd
Chemische Synthese (DE-588)4133806-6 gnd
Biosynthese (DE-588)4006902-3 gnd
subject_GND (DE-588)4045539-7
(DE-588)4057699-1
(DE-588)4140190-6
(DE-588)4133806-6
(DE-588)4006902-3
(DE-588)4143413-4
title Biosynthesis of tetrapyrroles
title_auth Biosynthesis of tetrapyrroles
title_exact_search Biosynthesis of tetrapyrroles
title_full Biosynthesis of tetrapyrroles ed. P. M. Jordan
title_fullStr Biosynthesis of tetrapyrroles ed. P. M. Jordan
title_full_unstemmed Biosynthesis of tetrapyrroles ed. P. M. Jordan
title_short Biosynthesis of tetrapyrroles
title_sort biosynthesis of tetrapyrroles
topic Pyrroles metabolism
Tetrapyrroles Synthesis
Pflanzen (DE-588)4045539-7 gnd
Stoffwechsel (DE-588)4057699-1 gnd
Tetrapyrrole (DE-588)4140190-6 gnd
Chemische Synthese (DE-588)4133806-6 gnd
Biosynthese (DE-588)4006902-3 gnd
topic_facet Pyrroles metabolism
Tetrapyrroles Synthesis
Pflanzen
Stoffwechsel
Tetrapyrrole
Chemische Synthese
Biosynthese
Aufsatzsammlung
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volume_link (DE-604)BV000003914
work_keys_str_mv AT jordanpeterm biosynthesisoftetrapyrroles