Cofactor Biosynthesis: A Mechanistic Perspective (eBook)

Cover 1
Contents 8
Preface 12
Chapter 1. Biosynthesis of Riboflavin 14
I. Introduction 15
II. An Overview of the Riboflavin Biosynthetic Pathway 16
III. Riboflavin Is Formed from a Purine Precursor via Diaminopyrimidine Intermediates 21
IV. GTP Cyclohydrolase II 22
V. Reductase and Deaminase 24
VI. An Elusive Phosphatase 25
VII. 3,4-Dihydroxy-2-butanone 4-Phosphate Synthase 25
VIII. Lumazine Synthase 29
IX. Riboflavin Synthase 33
X. Riboflavin Synthase Paralogs in Bioluminescence 36
XI. Riboflavin Synthase of Archaebacteria 37
XII. The Lumazine Synthase/Riboflavin Synthase Complex of Bacillaceae 38
XIII. Flavokinase and FAD Synthetase 38
XIV. Riboflavin Production by Fermentation 39
XV. Inhibitors of Riboflavin Biosynthesis 40
XVI. Biosynthesis of Riboflavin in Plants 42
XVII. Regulation of Riboflavin Biosynthesis in Bacillus subtilis 42
XVIII. Biosynthesis of 5-Deaza-7,8-didemethyl-8-hydroxyriboflavin 42
XIX. Biosynthesis of Molybdopterin 44
XX. Conclusion 46
References 50
Chapter 2. Biosynthesis of Biotin and Lipoic Acid 64
I. Biosynthesis of Biotin 65
II. Biosynthesis of Lipoic Acid 98
III. Conclusion 103
References 104
Chapter 3. The Biosynthesis of Nicotinamide Adenine Dinucleotides in Bacteria 116
I. Introduction 117
II. The NAD(P) Biosynthetic Pathway in Bacteria 117
III. The Biosynthetic Enzymes 117
IV. The Enzymes of NAD(P) Recycling and Salvage 125
V. Regulation of NAD(P) Biosynthesis 127
VI. NAD(P) Biosynthesis in Eukaryotes 127
VII. NAD(P) in Human Nutrition 128
VIII. Summary and Conclusions 129
References 129
Chapter 4. Biosynthesis of Vitamin B6 and Structurally Related Derivatives 134
I. Introduction 134
II. Biosynthesis of Vitamin B6 in Escherichia coli 136
III. Biosynthesis of Ginkgotoxin in Ginkgo biloba 159
IV. Conclusions 162
References 162
Chapter 5. The Biosynthesis of Coenzyme A in Bacteria 170
I. Introduction 171
II. The Coenzyme A Biosynthetic Pathway in Bacteria 171
III. Regulation of Coenzyme A Biosynthesis in Escherichia coli 179
IV. Coenzyme A Biosynthesis in Saccharomyces cerevisiae 179
V. Coenzyme A in Human Nutrition 179
VI. Summary and Conclusions 180
References 181
Chapter 6. Biosynthesis of Menaquinone (Vitamin K2) and Ubiquinone (Coenzyme Q): A Perspective on Enzymatic Mechanisms 186
I. Introduction 187
II. Menaquinone Biosynthesis 190
III. Ubiquinone Biosynthesis 204
IV. Biosynthesis of the Polyprenyl Side Chain 212
V. Comparison of Coenzyme Q Biosynthesis in Yeast and Escherichia coli 218
VI. Conclusions 221
References 223
Chapter 7. Mechanisms of Biosynthesis of Protein-Derived Redox Cofactors 232
I. Introduction 232
II. Biological Significance 234
III. Discoveries of Protein-Derived Redox Cofactors 235
IV. Biogenesis of Trihydroxyphenylalanine Quinone 236
V. Biogenesis of Tryptophan Tryptophylquinone 241
VI. Biogenesis of Lysine Tyrosyl Quinone 244
VII. Biogenesis of the Cofactor in Galactose Oxidase 244
VIII. General Mechanistic Considerations 247
IX. Conclusion 249
References 249
Chapter 8. L-Ascorbic Acid Biosynthesis 254
I. Introduction 255
II. The Biosynthetic Pathway of Ascorbate in Mammals 257
III. The Biosynthetic Pathway of Ascorbate in Higher Plants 265
IV. D-Erythroascorbate Synthesis in Yeast 271
V. Evolution of Ascorbate Biosynthesis 272
VI. Conclusions 273
References 274
Chapter 9. Multiple Biosynthetic Pathways for Vitamin B12: Variations on a Central Theme 280
I. Introduction 280
II. The Genes and Enzymes Required for the Biosynthesis of Cobalamin from Aminolevulinic Acid 282
III. Are There Other Variations in the Route to Vitamin B12? 304
IV. Conclusions 306
References 306
Chapter 10. Biosynthesis of the Methanogenic Cofactors 312
I. Introduction 312
II. Biosynthesis of Methanopterin 313
III. Biosynthesis of Coenzyme B 324
IV. Biosynthesis of Methanofuran 328
V. Biosynthesis of Coenzyme F420 337
VI. Biosynthesis of Coenzyme M 343
References 343
Appendixes 352
A.1 The Biosynthesis of Thiamin Pyrophosphate in Escherichia coli 353
A.2 The Biosynthesis of Tocopherol (Vitamin E) 356
A.3 The Biosynthesis of Retinal 358
A.4 The Biosynthesis of Calcitriol (Dihydroxy Vitamin D3) 359
A.5 The Biosynthesis of Pyrroloquinoline Quinone 361
A.6 The Biosynthesis of Folate 362
A.7 The Biosynthesis of Molybdopterin Guanine Dinucleotide 365
Index 368