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Redaktion: Karsten Krohn
Anthracycline Chemistry and Biology I
Biological Occurence and Biosynthesis, Synthesis and Chemistry
erschienen Juli 2008 324 Seiten, Gebunden
Springer-Verlag GmbH & Co. KG | ISBN: 3540758143
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| VORWORT | öffnen |
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Preface More than 15 years have passed since publication of the last monograph on anthracycline antibiotics, the ACS Symposium Series 574, edited by W. Priebe. However, anthracycline antibiotics continue to be one of the most applied antitumor agents, mostly in combination therapy. In addition, a number of exciting new developments such as prodrug development or new synthetic, semi-synthetic, or biosynthetic derivatives have emerged in spite of a certain decrease in synthetic activity. With this...
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TOPICS IN CURRENT CHEMISTRY Anthracycline Chemistry and Biology I Volume Editor K. Krohn Biological Occurrence and Biosynthesis H. Laatsch • S. Fotso NaturallyOccurring Anthracyclines J. Niemi • M. Metsä-Ketelä Biosynthetic Anthracycline Variants G. Schneider • P. Mäntsälä •M. Metsä-Ketelä • J. Niemi• P. Mäntsälä • G. Schneider Anthracycline Biosynthesis: Genes, Enzymes and Mechanisms Synthesis and Chemistry 0. Achmatowicz• B. Szechner Synthesis of Enantiomerically Pure ... [weiter lesen] |
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Contents Part I Biological Occurence and Biosynthesis Naturally Occurring Anthracyclines H. Laatsch • S. Fotso 3 Biosynthetic Anthracycline Variants J. Niemi • M. Metsä-Ketelä • G. Schneider • P. Mäntsälä75 Anthracycline Biosynthesis: Genes, Enzymes and Mechanisms M. Metsä-Ketelä • J. Niemi • P. Mäntsälä • G. Schneider 101 Part II Synthesis and Chemistry Synthesis of Enantiomerically Pure Anthracyclinones O. Achmatowicz • B. Szechner 143 Combinatorial Synthesis of Linearly Condensed Polycyclic Compounds, Including ... P. Vogel 187 Fluorinated Anthracyclines G. Giannini • D. Alloatti 215 Synthesis of the Sugar Moieties G. Grynkiewicz • W. Szeja 249 Nonnatural Glycosyl Anthraquinones as DNA Binding and Photocleaving Agents K... Syntheses of Anthracyclines and Fredericamycin A via Strong Base-Induced Cyc... Y. Kita • H. Fujioka 299 Subject Index 321
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Subject Index AAclacinomycins 19, 78, 80, 82, 85, 121 - , sugar modification 132 Acosamine 256 Actinorhodin 89, 106 Acyl carrier protein 109 Adriamycin see Doxorubicin Adriamycinone 25 Aglycones 5 - , modification 79 - , pathway engineering 89 Aklanonic acid 114 - , starter units 109 - , to aglycones 118 Aklavin 19 Aklavinone 11-hydroxylase 85 Aklavinones 17, 19, 119, 157 - , conversion to doxorubicin 129 Alldimycin-A 23 Aloesaponarin II 89 3-Amino-2, 3, 6-trideoxy-Lyxo- - hexopyranose (L-daunosamine) 249, 259 6-[[(Aminoalkyl)oxy]methyl]-6, 7- - dideoxyidarubicinones 205 Anthracycline antibiotics 143, 249, 306 - sugars 252 Anthracycline glycosylation 85 Anthracyclines, 1, 4, 6, 11 -tetrahydroxyanthraquinone 28 - biosynthesis 105 - D-ring types 6 - dihydroxyanthraquinones 17 - enantiopure 150 - fluorinated 218 - fluorinated esters 234 - fluorine-incorporating prodrugs 243 - isolation 7 - , structures 103 - , sugar moiety 16 - , unusual 29 Anthracyclinones 19, 143 - , combinatorial approach 189 - , isolation 7 Anthraquinone-carbohydrate hybrids 290 Antibiotic sugar analogs 272 Anticancer therapy, most important antibiotics 25 Antituberculosis activity, quinocylines 18 Antitumor agents, fluorinated 216 Aranciamycins 92, 104, 163 Arugomycin 29 Auramycin 19 Avermectin 92 BBaumycins 86, 129 Bioconversion, genetically engineered - strains 95 Biosynthesis 101 Biotransformation (bioconversion) 94 1, 4-Bis[ (aminoalkyl)amino] -9, 10 - anthraquinones 205 Bleomycin 22 Brasiliose 23 Butyl olivoside 257 CCarborubicin 27 Cardiotoxicity 4, 102 Carminomycin 80 Carminomycinone 25 Celastramycins 18 Chemoenzymatic synthesis 96 Chiral auxiliaries 158, 272 Chiral pool 163 Chiral substrates, non-natural 175 Chloronaphthoquinone acetal 307 Ciclamycin A 22 Cinerubins 15, 22, 80 Cinerulose A 253, 256 Citromycinones 17, 20, 80, 157 Combinatorial biosynthesis 75, 94 Cosmomycin D 104 Cycloaddition 303 - strong base-induced 299 - Daunomycin 4, 25 - biosynthesis genes 107 Daunomycinones 25, 173, 175, 253, 307 - Diels-Alder regioselectivity 195 Daunorubicin 85, 102, 146, 188, 252 Daunorubicinone 232 Daunosamine (DN) 16, 20, 85, 249, 259 Decilorubicin 30 4-Demethoxy-11 -deoxyadriamycin 17 4-Demethoxyfeudomycinone C 165 11... Deoxycarminomycinone 21 11-Deoxydaunomycin 200 Deoxydaunomycinone 200 2-Deoxy-L-fucose 85, 256 7-Deoxyidarubicinone 155, 232 2-Deoxy... ll-Deoxy?-rhodomycin A 96 2-Deoxysugars 122 4-Deoxysulfurmycinone 17 Desacetyladriamycin 96 Desoxyerythrolaccin 89 Desymmetrization 188 Diastereoselective synthesis 143 2, 6-Dideoxypyranose 249 Diels-Alder additions, tandem, - regiostereoselective 198 Diels-Alder reactions 188 Dienophiles, desymmetrization with - enantiomerically pure 202 14, 14-Difluoroanthracycline 233 1, 4-Difluoroanthracycli... DDihydroxylation 151 Dimroth principle 191 Diquinones 19 Disaccharide fluoroanthracyclines 242 DNA 285 DNA cleavage, photoinduced, - anthraquinone-carbohydrate hybrids 292 DNA photocleavers 290 DNA strand religation 188 DoxA 81 Doxorubicin (DOXO) 4, 25, 102, 146, 188, 217, 251 dTDP-L-2-deoxyfucose 125 dTDP-L-2-deoxynogalamine 127 dTDP-4-keto-6-deoxy-D-glucose 122 dTDP-L-nogalose 127 dTDP-L-rhodinose 125 dTDP-L-rhodosamine 126 Dynemicin A 306 EEnantioselective catalysis 143, 177 Enantioselective dihydroxylations 154 Enantioselective syntheses 268 Enzymes, biosynthetic 109 - engineering 96 Enzymology 101 Epelmycin 80 Epirubicin 93 Epoxidation 151, 155 Erythromycin 92 F - F 840020 21 FAD hydroxylase 85 Feudomycinones A 25 Fluorinated antitumor agents 216 Fluorine, A-ring 222 - , B-ring 221 - , C-14 232 - , D-ring 219 - , sugar moiety 236 Fluorine-incorporating prodrugs 243 2-Fluoro anthracyclines 2213' -Fluoroalkylaminoan... Fluoroanthracyclines 216 - , disaccharide 242 1-Fluoroanthracyclines 2192'-Fluoroanthracyclines 236 - 3-Fluoroanthracyclines 221 3'-Fluoroanthracyclines 237 4'-Fluoroanthracyclines 238 ... - Fluoroanthracyclines 221 13-Fluoroanthracyclines 230 14-Fluoroanthracyclines 232 Fredericamycin A 299, 312 Furans 188 GGaltamycinone 306 Genetic engineering, production strains 88 4-0-(/?-D-Glucopyranosyl)-s- - rhodomycinone 26 Glucose to deoxysugars 122 Glucose-1-phosphate to 2-deoxysugars 122 Glycosyl anthraquinones, nonnatural, DNA - binders 286 - DNA photocleavers 290 Glycosylating agents, daunosamine 259 Glycosylation 128, 249 - engineering 92 HHex-1-enitol (L-fucal) 256 Histomodulin 26 Homophthalic anhydride 299, 301 Hybrid antibiotics 89 Hydrazoic acid 260 11-Hydroxyaclacinomycin-X 91 2-Hydroxyaklavinone 24 6-Hydroxyanthr... Hydroxylation 132, 155 10-Hydroxyldesacetyladriamycin 96 pen'-Hydroxyquinones 8 1-Hydroxyserirubicin 23 1-Hydroxysulfurmycin T 22 IIdarubicin (4-demethoxydaunorubicin) 21, 146 - analogues 149 Idarubicinone 149, 170 Intercalation 285 Iosoxantrone 205 Isoquinocycline A 18 Isorhodomycinones 28 Isorhodomycins 80 KKetosynthase 109 Kinetic desymmetrization 191 Komodoquinones 25, 29 Kosinostatin 18 LLactonamycin 306 Leucoquinizarine 163 Leukemia 23, 26 MMaggiemycin 81 Malonyltransferase 109 Mass spectra 15 Medorubicin (4-demethoxyadriamycin) 21 Methyl transfer 130 Methyl trifluoromethyl dioxirane 227 1-O-Methyldesoxyerythrolaccin 89 4-O-Methylepelm... Methylester hydrolysis 131 Microbial metabolites 3 Mitoxantrone 205 Monorhodosaminosides 22 Mutactimycins 25, 27 Mutants, blocked, production strains 95 Mycaminose 25 NNatural products 3 NMR spectra 9 - Nocardicyclin 22 Nogalamine 29 Nogalarol 21, 29 Nogalaviketone 122 Nogalavinone 119 Nogalomycins 78, 86, 104, 252 Nogalonic acid 114 Nogarol 29 Nothramicin 23 OOlivose/olivosides 256 Oxaunomycin 27, 306, 308
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