Dynamic aspects of natural products chemistry molecular biological approaches
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1997
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| 245 | 1 | 0 | |a Dynamic aspects of natural products chemistry |b molecular biological approaches |c ed. by Kyozo Ogura ... |
| 264 | 1 | |a Tokyo |b Kodansha [u.a.] |c 1997 | |
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| 650 | 4 | |a Biochemistry | |
| 650 | 4 | |a Natural products |x Structure | |
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Datensatz im Suchindex
| _version_ | 1819646228183384064 |
|---|---|
| adam_text | Dynamic Aspects of
Natural Products Chemistry
—Molecular Biological Approaches
Edited by
Kyozo Ogura
Professor, Tohoku University, Sendai, Japan
and
Ushio Sankawa
Professor, Toyarna Medical and Pharmaceutical University, Toyama, Japan
© btap
Kodansha harwood academic publishers
Australia • Canada • China • France • Germany • India
Japan •Luxembourg-Malaysia-The Netherlands-Russia
Singapore*Switzerland*Thailand-United Kingdom
Contents
Preface xiii
List of Contributors xv
1 Mechanistic Enzymology and Molecular Genetics of Chain Elongation in Isoprenoid
Biosynthesis 1
Kyozo Ogura and Tanetoshi Koyama
1 1 Introduction 1
1 2 Farnesyl Diphosphate Synthase 1
121 Occurrence and functions 1
122 Molecular cloning and overexpression 2
123 Comparative primary structures and site-directed mutagenesis 4
124 Mechanistic considerations 12
125 Crystallization and three-dimensional structure IS
1 3 Geranylgeranyl Diphosphate Synthase 15
1 4 Bacterial Prenyltransferases 16
141 Medium-chain prenyl diphosphate synthases 16
142 Long-chain £-prenyl diphosphate synthases 18
143 Z-Prenyl diphosphate synthases 20
144 Stereochemistry of prenyltransferase reactions 21
1 5 Summary 21
2 Biosynthesis of Isoflavone and Related Compounds in Tissue Cultures of
Pueraria lobata 25
Ushio Sankawa and Takashi Hakamatsuka
2 1 Introduction 25
2 2 Formation of the Flavonoid Skeleton by Chalcone Synthase 27
221 Effects of elicitor on the formation of isoflavonoids 28
222 Chalcone synthase and reductase 30
223 Cloning and expression of chalcone synthase (CHS) and reductase (CHR) 32
224 Cloning of regulatory genes of chalcone synthase 35
viii Contents
2 3 Characterization of Chalcone-Flavanone Isomerase 38
231 Cloning of chalcone-flavanone isomerase 38
232 Expression and reaction mechanism of chalcone-flavanone isomerase 38
2 4 Characterization of Isoflavone Synthase 40
2 5 Purification and Characterization of Dehydratase that Forms Isoflavone 46
2 6 Perspective 46
3 Carotenoid Biosynthesis at the Gene Level 49
Norihiko Misawa
3 1 Introduction 49
3 2 Functional Analysis of Erwinia Carotenoid Biosynthesis Genes 50
321 Cloning of biosynthesis genes 51
322 Identification of a carotenoid end product 51
323 Identification of carotenoid intermediates 52
324 Elucidation of an Erwinia carotenoid biosynthetic pathway 55
3 3 Functional Analysis of Astaxanthin Biosynthesis Genes 57
331 Cloning of biosynthesis genes 60
332 Identification of astaxanthin and its intermediates 61
333 Elucidation of an astaxanthin biosynthetic pathway 64
334 Conservation of carotenoid biosynthesis between a marine bacterium and Erwinia species
3 4 Functional Analysis of Carotenoid Biosynthesis Genes from Other Organisms 66
341 Phytoene synthase genes 67
342 Phytoene desaturase genes 67
343 ^-Carotene desaturase genes 68
344 Lycopene cyclase genes 69
345 Genes for other carotenogenic enzymes 69
3 5 Perspectives 70
4 Biosynthesis of Monoterpenoids in Higher Plants:
Mechanisms of Chain Elongation and Chiral Center Generation 73
Takayuki Suga and Yoshikazu Hiraga
4 1 Introduction 73
4 2 Chain Elongation of the £-Prenyl Chain 75
421 Discovery and characterization of geranyl diphosphate synthase in higher plants 75
422 Stereochemical control in geranyl diphosphate biosynthesis by geranyl diphosphate
synthase 79
423 I3CNMR detection of delocalized Cio-allylic cation in the biosynthesis of farnesyl
diphosphate 81
4 3 Stereochemical Control in the Biosynthesis of Cyclic Monoterpenoids 83
431 Role of divalent metal ions in the conversion of geranyl diphosphate to cyclic
monoterpenoid 83
432 Generation of species-specific chirality in the biosynthesis of limonenes 87
433 Regioselective hydrogen elimination from the methyl group of geranyl diphosphate in the
8(9)-double bond formation of limonene 90
Contents ix
5 Biogeneration of So-called Green Odor Components by Plant Leaves 95
Akikazu Hatanaka
5 1 Introduction 95
5 2 Biosynthetic Pathways for Green Odor Components 96
521 Provision of substrate fatty acids 96
522 Formation of products 97
5 3 Enzymes Involved in Biogeneration of Green Odor Components 99
531 Distribution of the enzymes producing green odor components 99
532 Properties of the enzymes 99
533 Substrate and product specificities of the enzymes 102
534 Mechanisms of the enzyme reactions 109
5 4 Relationship of Enzyme Activities to the Environment 112
5 5 Perspectives 114
6 Biological Diels-Alder Reaction in Biosynthesis of Phytotoxins 119
Akitami Ichihara and Hideaki Oikawa
6 1 Introduction 119
6 2 Biosynthesis of Betaenones 120
621 Structural elucidation of betaenones 121
622 Synthesis of diplodiatoxin and betaenone C 123
623 Biosynthetic study of betaenones: Indirect evidence for biological Diels-Alder reaction
6 3 Biosynthesis of Chaetoglobosins 128
631 Structural features of chaetoglobosins 128
632 Biosynthetic study of chaetoglobosins: Indirect evidence for biological Diels-Alder
reaction 128
6 4 Biosynthesis of Solanapyrones 134
641 Chemical aspects of solanapyrones 134
642 Synthesis of solanapyrones A and D 135
643 Biosynthetic studies of solanapyrones: Direct evidence for biological Diels-Alder reaction
644 Diels-Alderase 139
6 5 Perspectives 141
7 Biosynthesis of Natural C-P Compounds, Bialaphos and Fosfomycin 145
Haruo Seto and Tomomi Hidaka
7 1 Introduction 145
7 2 Biosynthesis of Bialaphos 146
721 Origin of the carbon skeleton 146
722 Identification of biosynthetic intermediates 147
723 Formation reactions of C-P bonds 148
724 Chain elongation reaction, transformation of the C3 intermediate to the d intermediate
725 Other reactions 154
726 Molecular cloning of bialaphos biosynthetic genes 155
x Contents
7 3 Biosynthesis of Fosfomycin 156
731 Biosynthetic pathway of fosfomycin and intermediates 157
732 Molecular cloning of fosfomycin biosynthetic genes 159
7 4 Conclusion 161
8 Regulation of Antibiotic Production: Protein Serine/Threonine Kinases and
Autoregulators 165
Sueharu Horinouchi
8 1 Introduction 165
8 2 AfsR and AfsQl as Global Regulators for Secondary Metabolism 166
821 qfsR 167
822 afsQl 168
8 3 Protein Serine/Threonine Kinases as Global Regulators 170
831 Multiple protein kinases involved in secondary metabolism and morphogenesis 170
832 q/^T controlling antibiotic production in S coelicolor A3(2) 170
833 Possible involvement of an afsK homolog in morphogenesis in £, griseus 172
834 afsK2 controlling morphogenesis in S griseus 173
8 4 Autoregulators 174
841 Autoregulators controlling secondary metabolism and morphogenesis 174
842 A-Factor 176
843 A-Factor receptor protein 178
844 Regulation of streptomycin biosynthesis by A-factor 181
8 5 Concluding Remarks 185
9 Mechanistic Enzymology and Molecular Recognition of 3-Isopropylmalate Dehydro-
genase Derived from an Extreme Thermophile, Thermus thermophilus HB8 187
Katsumi Kakinuma
9 1 Introduction 187
9 2 Structure of 3-Isopropylmalate Dehydrogenase 188
921 Chemical synthesis of substrate 188
922 Enzyme purification 190
923 Crystallographic structure 190
9 3 Reaction Mechanism 191
931 Stereochemistry of hydride transfer reaction 191
932 Stereochemistry of decarboxylation reaction 192
9 4 Substrate Recognition 194
941 Enantioselective synthesis of substrate analogues 194
942 Hydrophobic interaction 196
943 Electrostatic interaction 197
9 5 Design of Fluorinated Analogues and Mechanistic Analysis 199
951 Synthesis of fluorinated analogues of IPM 199
952 Analysis of IPMDH reaction with a fluorinated analogue 201
9 6 Modification of 3-Isopropylmalate Dehydrogenase and Related Dehydrogenase
961 Site-directed mutagenesis of IPMDH 202
Contents xi
962 Spontaneous mutation 204
963 Site-directed mutagenesis of T thermophilus isocitrate dehydrogenase 204
9 7 Interactions of 3-lsopropylmalate Dehydrogenase with Substrate and Coenzyme
971 X-ray analysis of IPMDH-NAD+ complex 206
972 Molecular modeling of IPMDH-IPM-NAD+-metal2+ complex 206
9 8 Perspectives 207
10 Biosynthesis of Cyclic Bromo Ethers from Red Algae 209
Akio Murai
10 1 Introduction 209
10 2 Proposed Biogenetic Routes to Cyclic Bromo Ethers 211
10 3 Biosynthetic Studies on Cyclic Bromo Ethers with Lactoperoxidase 212
10 3 1 Model experiments 212
10 3 2 Lauthisan series 215
10 3 3 Laurenan series 216
10 4 Purification of Bromoperoxidase from Laurencia nipponica 218
10 5 Biosynthetic Studies on Cyclic Bromo Ethers with Bromoperoxidase 219
10 6 Present Status of Research 221
11 Molecular Biology and Engineering of Biosynthesis of Cysteine and
Biogenetically Related Non-protein Amino Acids in Plants 227
Kazuki Saito
11 1 Introduction 227
11 2 Natural Occurrence of Non-protein /3-Substituted Alanines 227
11 3 General Biosynthetic Route of Non-protein ^-Substituted Alanines 229
11 3 1 Biogenetic relation with cysteine biosynthesis 229
11 3 2 Origins of heterocyclic rings 229
11 3 3 Biosynthesis of ^-C-substituted alanines 230
11 4 Molecular Cloning of Cysteine Synthases and Related Enzymes 230
11 4 1 Cysteine/j8-PA synthase 230
11 4 2 Serine acetyltransferase 233
11 4 3 Regulation of biosynthetic flow 235
11 5 Molecular Engineering 236
11 5 1 Mechanistic study by site-directed mutagenesis and evolution 236
11 5 2 Over-expression and production in prokaryotes 238
11 5 3 Transgenic plants 240
11 6 Future Prospects 242
12 Pharmacological Applications of Physiologically Active Natural Products 245
Yasushi Ohizumi
12 1 Introduction 245
12 2 Elucidation of Molecular Mechanisms of Ion Channels 246
12 2 1 Na channels 246
xii Contents
12 22K channels 250
12 2 3 Ca channels 251
12 3 Elucidation of Molecular Mechanism of Excitation-Contraction Coupling of Muscle
12 3 1 Ca release channels 254
12 3 2 Capump 258
12 4 Mechanistic Studies of Contractile Proteins 260
12 4 1 Myosin 260
12 4 2 Actin 262
12 5 Characterizing Key Enzymes in Intracellular Signaling 263
12 5 1 Phosphatases 263
12 5 2 Protein kinases 263
12 5 3 Phosphoinositide 3-kinase 265
13 Mechanisms in New Bioluminescence Systems 269
Mamoru Ohashi
13 1 Introduction 269
13 1 1 Luciferin-luciferase reaction 269
13 1 2 Photoproteins 269
13 1 3 Quantum yield of bioluminescence 270
13 1 4 Ultraweak chemiluminescence 270
13 2 Chemiluminescence and Bioluminescence of Imidazopyrazines 270
13 2 1 Cypridina (Vargula) luciferin 270
13 2 2 Bioluminescence of jellyfish Aequorea victoria 271
13 2 3 Chemiluminescence of coelenterazine and its analogs 273
13 2 4 Structure-activity relationship in aequorin bioluminescence 276
13 2 5 Bioluminescence of aequorin 279
13 2 6 Green fluorescent protein 282
13 2 7 Other imidazopyrazine systems 284
13 3 Bioluminescence of New Systems 284
13 3 1 Color change in firefly bioluminescence 284
13 3 2 Fungal and bacterial bioluminescence 288
13 3 3 Dinoflagellate bioluminescence 289
13 3 4 Marine polychaete, Odontosyllis undecimonta 290
13 4 Mechanisms of Excited-State Formation by Chemical Reactions 290
13 4 1 Thermal decomposition of dioxetanes 290
13 4 2 Chemically initiated electron-exchange luminescence 290
Index 294
|
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| spellingShingle | Dynamic aspects of natural products chemistry molecular biological approaches Biochemistry Natural products Structure Naturstoff (DE-588)4041418-8 gnd |
| subject_GND | (DE-588)4041418-8 |
| title | Dynamic aspects of natural products chemistry molecular biological approaches |
| title_auth | Dynamic aspects of natural products chemistry molecular biological approaches |
| title_exact_search | Dynamic aspects of natural products chemistry molecular biological approaches |
| title_full | Dynamic aspects of natural products chemistry molecular biological approaches ed. by Kyozo Ogura ... |
| title_fullStr | Dynamic aspects of natural products chemistry molecular biological approaches ed. by Kyozo Ogura ... |
| title_full_unstemmed | Dynamic aspects of natural products chemistry molecular biological approaches ed. by Kyozo Ogura ... |
| title_short | Dynamic aspects of natural products chemistry |
| title_sort | dynamic aspects of natural products chemistry molecular biological approaches |
| title_sub | molecular biological approaches |
| topic | Biochemistry Natural products Structure Naturstoff (DE-588)4041418-8 gnd |
| topic_facet | Biochemistry Natural products Structure Naturstoff |
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