Chemical synthesis of hormones, pheromones and other bioregulators:
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| Main Author: | |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
Chichester
Wiley
2010
|
| Edition: | 1. publ. |
| Series: | Postgraduate chemistry series
|
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Item Description: | Includes bibliographical references and index |
| Physical Description: | XIV, 299 S. graph. Darst. |
| ISBN: | 9780470697245 9780470697238 |
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| 245 | 1 | 0 | |a Chemical synthesis of hormones, pheromones and other bioregulators |c Kenji Mori |
| 250 | |a 1. publ. | ||
| 264 | 1 | |a Chichester |b Wiley |c 2010 | |
| 300 | |a XIV, 299 S. |b graph. Darst. | ||
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| 490 | 0 | |a Postgraduate chemistry series | |
| 500 | |a Includes bibliographical references and index | ||
| 650 | 4 | |a Bioorganic chemistry | |
| 650 | 4 | |a Biomolecules |x Synthesis | |
| 650 | 4 | |a Hormones |x Synthesis | |
| 650 | 4 | |a Pheromones |x Synthesis | |
| 650 | 4 | |a Plant hormones |x Synthesis | |
| 650 | 4 | |a Hormones |x chemical synthesis | |
| 650 | 4 | |a Biological Factors |x chemical synthesis | |
| 650 | 4 | |a Pheromones |x chemical synthesis | |
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Record in the Search Index
| _version_ | 1804143258916356096 |
|---|---|
| adam_text | IMAGE 1
CONTENTS
PREFACE XI
ABBREVIATIONS XIII
1 INTRODUCTION-BIOFUNCTIONAL MOLECULES AND ORGANIC SYNTHESIS 1
1.1 WHAT ARE BIOFUNCTIONAL MOLECULES? 1
1.2 DEVELOPMENTAL STAGES OF STUDIES ON BIOFUNCTIONAL MOLECULES 1
1.3 SMALL AMOUNTS OF THE SAMPLES ARE NOW SUFFICIENT FOR THE ELUCIDATION
OF THE STRUCTURES OF BIOFUNCTIONAL MOLECULES 3
1.4 WHY MUST BIOFUNCTIONAL MOLECULES BE SYNTHESIZED? 4
1.5 HOW CAN WE SYNTHESIZE BIOFUNCTIONAL MOLECULES? 5
1.5.1 WHAT IS SYNTHESIS? 5
1.5.2 WHAT KIND OF CONSIDERATION IS NECESSARY BEFORE STARTING A
SYNTHESIS? 5
1.5.3 SYNTHON 6
1.5.4 MOLECULAR SYMMETRY AND SYNTHESIS 6
1.5.5 CRITERIA FOR A. GOOD SYNTHESIS 6
1.6 WHAT KIND OF KNOWLEDGE AND TECHNIQUES ARE NECESSARY TO SYNTHESIZE
BIOFUNCTIONAL MOLECULES? 10
1.6.1 STEREOCHEMISTRY AND REACTIVITY 10
1.6.2 STEREOCHEMISTRY AND ANALYTICAL METHODS 11
REFERENCES 16
2 SYNTHESIS OF PHYTOHORMONES, PHYTOALEXINS AND OTHER BIOFUNCTIONAL
MOLECULES OF PLANT ORIGIN 19
2.1 PHYTOHORMONES 19
2.1.1 WHAT ARE PHYTOHORMONES?
19
2.1.2 GIBBERELLINS 20
2.1.3 DITERPENES RELATED TO GIBBERELLINS 30
2.1.4 ABSCISIC ACID AND ITS RELATIVES-SYNTHESIS OF OPTICALLY ACTIVE
COMPOUNDS 38
2.1.5 BRASSINOSTEROIDS 41
2.1.6 PHYLLANTHRINOLACTONE, A LEAF-CLOSING FACTOR 45
2.2 PHYTOALEXINS 49
2.2.1 WHAT ARE PHYTOALEXINS?
49
2.2.2 SYNTHESIS OF PISATIN 49
2.2.3 SYNTHESIS OF 2-(4-HYDROXYPHENYL MAPHTHALENE-1,8-DICARBOXYLIE
ANHYDRIDE 52
2.2.4 SYNTHESIS OF ORYZALEXINS
53
2.2.5 SYNTHESIS OF PHYTOCASSANES
56
IMAGE 2
;/ CONTENTS
2.3 PLANT ALLELOCHEMICALS 59
2.3.1 SYNTHESIS OF GLYCINOECLEPIN A 59
2.3.2 SYNTHESIS OF STRIGOLACTONES 61
2.4 OTHER BIOACTIVE COMPOUNDS OF PLANT ORIGIN 67
2.4.1 SYNTHESIS OF ARNEBINOL 67
2.4.2 SYNTHESIS OF MAGNOSALICIN 68
2.4.3 SYNTHESIS OF HEMANDULCIN 69
2.4.4 SYNTHESIS OF O -METHYL PISIFERIC ACID 71
2.4.5 SYNTHESIS OF DIOSPYRIN 73
2.4.6 SYNTHESIS OF MISPYRIC ACID 73
REFERENCES 77
3 SYNTHESIS OF INSECT BIOREGULATORS OTHER THAN PHEROMONES 81
3.1 INSECT JUVENILE HORMONES 81
3.1.1 WHAT ARE INSECT HORMONES? 81
3.1.2 SYNTHESIS OF JUVABIONE 82
3.1.3 SYNTHESIS OF THE RACEMATES OF JUVENILE HORMONES 86
3.1.4 SYNTHESIS OF THE ENANTIOMERS OF JUVENILE HORMONES 88
3.2 INSECT ANTIFEEDANTS 95
3.2.1 SYNTHESIS OF POLYGODIAL 95
3.2.2 SYNTHESIS OF WARBURGANAL 97
3.2.3 SYNTHESIS OF 3,4 -DIHYDROXYPROPIOPHENONE 3-(3-D-GLUCOPYRANOSIDE 97
3.2.4 SYNTHESIS OF HOMOGYNOLIDE A 99
3.3 INSECT REPELLENTS 100
3.3.1 SYNTHESIS OF ROTUNDIAL 100
3.3.2 SYNTHESIS OF POLYZONIMINE 102
REFERENCES 104
4 SYNTHESIS OF PHEROMONES 107
4.1 WHAT ARE PHEROMONES? 107
4.2 METHODS FOR ENANTIOSELECTIVE SYNTHESIS 107
4.2.1 DERIVATION FROM ENANTIOPURE NATURAL PRODUCTS 108
4.2.2 ENANTIOMER SEPARATION (OPTICAL RESOLUTION) 108
4.2.3 ASYMMETRIC SYNTHESIS 109
4.2.4 DETERMINATION OF ENANTIOMERIC PURITY 109
4.3 WHY IS IT MEANINGFUL TO SYNTHESIZE ENANTIOPURE PHEROMONES? 110
4.3.1 DETERMINATION OF ABSOLUTE CONFIGURATION (1). TROGODERMAL 111
4.3.2 DETERMINATION OF ABSOLUTE CONFIGURATION (2). HEMIACETAL PHEROMONE
OF BIPRORULUS BIBAX 111
4.3.3 DETERMINATION OF ABSOLUTE CONFIGURATION (3). SESQUITERPENE
PHEROMONE OF EYSARCORIS LEWISI 118
4.3.4 CLARIFICATION OF THE RELATIONSHIP BETWEEN ABSOLUTE CONFIGURATION
AND PHEROMONE ACTIVITY-EJCO-BREVICOMIN 122
4.3.5 CLARIFICATION OF STRUCTURE (1). LINEATIN 124
4.3.6 CLARIFICATION OF STRUCTURE (2). AMERICAN COCKROACH PHEROMONE 126
IMAGE 3
CONTENTS VII
4.3.7 CLARIFICATION OF STRUCTURE (3). ACORADIENE 129
4.3.8 CLARIFICATION OF STRUCTURE (4). HIMACHALENE-TYPE PHEROMONE 130
4.3.9 PREPARATION OF A PURE SAMPLE FOR BIOASSAY (1). DISPARLURE 133
4.3.10 PREPARATION OF A PURE SAMPLE FOR BIOASSAY (2). JAPONILURE 137
4.3.11 PREPARATION OF A PURE SAMPLE FOR BIOASSAY (3). PHEROMONE OF THE
PALAEARCTIC BEE, ANDRENA WILKELLA 139
4.4 CHIRAL PHEROMONES WHOSE SINGLE ENANTIOMERS SHOW BIOACTIVITY 143
4.4.1 DIHYDROACTINIDIOLIDE, A PHEROMONE COMPONENT OF THE RED IMPORTED
FIRE ANT 143 4.4.2 LARDOLURE, THE AGGREGATION PHEROMONE OF THE ACARID
MITE 145
4.4.3 PHEROMONE OF THE FALL WEBWORM MOTH 148
4.4.4 POSTICLURE, THE FEMALE SEX PHEROMONE OF ORGYIA POSTICA 151
4.4.5 FARANAL, THE TRAIL PHEROMONE OF THE PHARAOH S ANT 151
4.4.6 (15,,3 S ,7/?)-3-METHYL-OT-HIMACHALENE, THE MALE SEX PHEROMONE OF
THE SANDFLY FROM JACOBINA, BRAZIL 153
4.4.7 (5)-9-METHYLGERMACRENE-B, THE MALE SEX PHEROMONE OF THE SANDFLY
FROM LAPINHA, BRAZIL 153
4.4.8 (L,5I?)-FRONTALIN, THE BARK BEETLE PHEROMONE 153
4.4.9 (LJR,5S,7I?)-3,4-DEHYDRO-EXO-BREVICOMIN AND
(S)-2-SEC4DUTYL-4,5-DIHYROTHIAZOLE, THE PHEROMONE COMPONENTS OF THE MALE
MOUSE 156
4.5 CHIRAL PHEROMONES WHOSE STEREOCHEMISTRY-BIOACTIVITY RELATIONSHIPS
ARE DIVERSE AND COMPLICATED 158
4.5.1 SULCATOL, THE PHEROMONE OF GNATHOTRICHUS SULCATUS 158
4.5.2 SEX PHEROMONE COMPONENTS OF FEMALE GERMAN COCKROACH 159
4.5.3 STIGMOLONE, THE PHEROMONE OF A MYXOBACTERIUM STIGMATELLA
AURANTIACA 166 4.5.4 IPSENOL AND IPSDIENOL, PHEROMONES OF IPS BARK
BEETLES 167
4.5.5 SERRICORNIN, THE CIGARETTE BEETLE PHEROMONE 168
4.5.6 STEGOBINONE, THE DRUGSTORE BEETLE PHEROMONE 171
4.5.7 SUPELLAPYRONE, THE SEX PHEROMONE OF THE BROWNBANDED COCKROACH 176
4.5.8 OLEAN, THE SEX PHEROMONE OF THE OLIVE FRUIT FLY 178
4.5.9 13,23-DIMETHYLPENTATRIACONTANE AS THE SEX PHEROMONE OF A TSETSE
FLY 181 4.6 SIGNIFICANCE OF CHIRALITY IN PHEROMONE SCIENCE 182
REFERENCES 184
5 SYNTHESIS OF BIOFUNCTIONAL MOLECULES OF MICROBIAL ORIGIN 189
5.1 MICROBIAL HORMONES 189
5.1.1 A-FACTOR 189
5.1.2 SCH II AND RELATIVES, THE FRUITING-INDUCING CEREBROSIDES 191
5.1.3 BASIDIFFERQUINONE C 195
5.1.4 SCLEROSPORIN 196
5.1.5 SPOROGEN-AO 1 197
5.1.6 DIFFEROLIDE 199
5.2 ANTIBIOTICS 201
5.2.1 ASCOCHLORIN 202
5.2.2 ASCOFURANONE 204
5.2.3 TRICHOSTATIN A 206
IMAGE 4
CONTENTS
5.2.4 KONINGININ A 207
5.2.5 CYTOXAZONE 213
5.2.6 NEUCHROMENIN 214
5.2.7 NOCARDIONE A AND B 215
5.2.8 CYTOSPORONE E 216
5.3 OTHER BIOACTIVE METABOLITES OF MICRO-ORGANISMS 219
5.3.1 MONOCERIN 219
5.3.2 PINTHUNAMIDE 219
REFERENCES 221
6 SYNTHESIS OF MARINE BIOREGULATORS, MEDICINALS AND RELATED COMPOUNDS
223 6.1 MARINE NATURAL PRODUCTS OF ECOLOGICAL IMPORTANCE SUCH AS
ANTIFEEDANTS 223
6.1.1 STYPOLDIONE 223
6.1.2 MESO- AND ()-LIMATULONE 226
6.1.3 TESTUDINARIOL A 227
6.1.4 STELLETTADINE A 232
6.2 MARINE NATURAL PRODUCTS OF MEDICINAL INTEREST 232
6.2.1 PUNAGLANDIN 4 232
6.2.2 BIFURCARENONE 235
6.2.3 ELENIC ACID 238
6.2.4 SYMBIORARNIDE 240
6.2.5 PENAZETIDINE A 242
6.2.6 PENARESIDIN A AND B 242
6.2.7 SULFOBACIN A, B AND FLAVOCRISTAMIDE A 245
6.2.8 PLAKOSIDE A 245
6.3 GLYCOSPHINGOLIPIDS AND SPHINGOLIPIDS OF MEDICAL INTEREST 252
6.3.1 ESTERIFIED CEREBROSIDE OF HUMAN AND PIG EPIDERMIS 252
6.3.2 CERAMIDE B, 6-HYDROXYLATED CERAMIDE IN HUMAN EPIDERMIS 256
6.3.3 KRN7000, A GLYCOSPHINGOLIPID THAT STIMULATES NATURAL KILLER T CELL
258
6.3.4 ANALOGS OF KRN7000 PREPARED IN 2003-2006 260
6.3.5 CYCLITOL, CARBASUGAR AND MODIFIED D-GALACTOSE ANALOGS OF KRN7000:
RCAI-56 AND RCAI-61 262
REFERENCES 264
7 SYNTHETIC EXAMINATION OF INCORRECTLY PROPOSED STRUCTURES OF
BIOMOLECULES 267 7.1 ORIGIN OF INCORRECT OR OBSCURE STRUCTURES 267
7.2 STRUCTURE FABRICATIONS OF HISTORICAL INTEREST 268
7.2.1 KOGL S AUXIN-A AND -B, THE PLANT-GROWTH PROMOTERS 268
7.2.2 CHEMICAL COMMUNICATION SYSTEM OF THE GREEN FLAGELLATE,
CHLAMYDOMONAS 270 7.2.3 EARLY FABRICATIONS OF THE STRUCTURES OF INSECT
PHEROMONES 275
7.3 INCORRECT STRUCTURES RESULTING FROM INAPPROPRIATE USE OF
PURIFICATION OR ANALYTICAL METHODS 276 7.4 INAPPROPRIATE STRUCTURAL
PROPOSAL CAUSED BY PROBLEMS IN BIOASSAY METHODS 278
7.4.1 BLATTELLASTANOSIDE A AND B, PUTATIVE COMPONENTS OF THE AGGREGATION
PHEROMONE OF THE GERMAN COCKROACH 278
IMAGE 5
CONTENTS IX
7.4.2
2,2A4-TETRAMETHYL-A^,A^-BIS(2,6-DIMETHYLPHENYL)CYCLOBUTANE-L,3-DIIMINE
AS A PUTATIVE ANTIFEEDANT AGAINST THE COTTON BOLL WEEVIL 284
7.5 HUMAN ERRORS ARE INEVITABLE IN CHEMISTRY, TOO 285
REFERENCES 287
8 CONCLUSION-SCIENCE AS A HUMAN ENDEAVOR 289
8.1 SMALL MOLECULES ARE ALSO BEAUTIFUL 289
8.2 CONTINUOUS EFFORTS MAY BRING SOMETHING MEANINGFUL 290
8.3 CAN A SCIENTIST EVENTUALLY HAVE A HOPE IN THE FUTURE? 291
ACKNOWLEDGEMENTS 291
INDEX 293
|
| any_adam_object | 1 |
| author | Mori, Kenji |
| author_facet | Mori, Kenji |
| author_role | aut |
| author_sort | Mori, Kenji |
| author_variant | k m km |
| building | Verbundindex |
| bvnumber | BV036645726 |
| classification_rvk | VK 8500 |
| ctrlnum | (OCoLC)699708669 (DE-599)BVBBV036645726 |
| discipline | Chemie / Pharmazie |
| edition | 1. publ. |
| format | Book |
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| id | DE-604.BV036645726 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T22:44:49Z |
| institution | BVB |
| isbn | 9780470697245 9780470697238 |
| language | English |
| lccn | 2010013112 |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-020565369 |
| oclc_num | 699708669 |
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| physical | XIV, 299 S. graph. Darst. |
| publishDate | 2010 |
| publishDateSearch | 2010 |
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| publisher | Wiley |
| record_format | marc |
| series2 | Postgraduate chemistry series |
| spelling | Mori, Kenji Verfasser aut Chemical synthesis of hormones, pheromones and other bioregulators Kenji Mori 1. publ. Chichester Wiley 2010 XIV, 299 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Postgraduate chemistry series Includes bibliographical references and index Bioorganic chemistry Biomolecules Synthesis Hormones Synthesis Pheromones Synthesis Plant hormones Synthesis Hormones chemical synthesis Biological Factors chemical synthesis Pheromones chemical synthesis Organische Synthese (DE-588)4075695-6 gnd rswk-swf Naturstoff (DE-588)4041418-8 gnd rswk-swf Naturstoffchemie (DE-588)4171332-1 gnd rswk-swf Naturstoffchemie (DE-588)4171332-1 s DE-604 Naturstoff (DE-588)4041418-8 s Organische Synthese (DE-588)4075695-6 s OEBV Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=020565369&sequence=000003&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Mori, Kenji Chemical synthesis of hormones, pheromones and other bioregulators Bioorganic chemistry Biomolecules Synthesis Hormones Synthesis Pheromones Synthesis Plant hormones Synthesis Hormones chemical synthesis Biological Factors chemical synthesis Pheromones chemical synthesis Organische Synthese (DE-588)4075695-6 gnd Naturstoff (DE-588)4041418-8 gnd Naturstoffchemie (DE-588)4171332-1 gnd |
| subject_GND | (DE-588)4075695-6 (DE-588)4041418-8 (DE-588)4171332-1 |
| title | Chemical synthesis of hormones, pheromones and other bioregulators |
| title_auth | Chemical synthesis of hormones, pheromones and other bioregulators |
| title_exact_search | Chemical synthesis of hormones, pheromones and other bioregulators |
| title_full | Chemical synthesis of hormones, pheromones and other bioregulators Kenji Mori |
| title_fullStr | Chemical synthesis of hormones, pheromones and other bioregulators Kenji Mori |
| title_full_unstemmed | Chemical synthesis of hormones, pheromones and other bioregulators Kenji Mori |
| title_short | Chemical synthesis of hormones, pheromones and other bioregulators |
| title_sort | chemical synthesis of hormones pheromones and other bioregulators |
| topic | Bioorganic chemistry Biomolecules Synthesis Hormones Synthesis Pheromones Synthesis Plant hormones Synthesis Hormones chemical synthesis Biological Factors chemical synthesis Pheromones chemical synthesis Organische Synthese (DE-588)4075695-6 gnd Naturstoff (DE-588)4041418-8 gnd Naturstoffchemie (DE-588)4171332-1 gnd |
| topic_facet | Bioorganic chemistry Biomolecules Synthesis Hormones Synthesis Pheromones Synthesis Plant hormones Synthesis Hormones chemical synthesis Biological Factors chemical synthesis Pheromones chemical synthesis Organische Synthese Naturstoff Naturstoffchemie |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=020565369&sequence=000003&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT morikenji chemicalsynthesisofhormonespheromonesandotherbioregulators |