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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
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... [weiter lesen]
KLAPPENTEXT |  öffnen
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]
INHALTSVERZEICHNIS |  öffnen
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
[weiter lesen]  
 
REGISTER |  öffnen
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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