The biosynthesis of steroids, terpenes, and acetogenins
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| Hauptverfasser: | , |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
New York, NY [u.a.]
Benjamin
1964
|
| Schriftenreihe: | Frontiers in chemistry
|
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
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| 100 | 1 | |a Richards, John H. |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a The biosynthesis of steroids, terpenes, and acetogenins |c John H. Richards and James B. Hendrickson |
| 264 | 1 | |a New York, NY [u.a.] |b Benjamin |c 1964 | |
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| 336 | |b txt |2 rdacontent | ||
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| 490 | 0 | |a Frontiers in chemistry | |
| 650 | 4 | |a Acetates | |
| 650 | 4 | |a Biochemistry | |
| 650 | 4 | |a Biosynthesis | |
| 650 | 4 | |a Steroids | |
| 650 | 4 | |a Terpenes | |
| 650 | 0 | 7 | |a Polyketide |0 (DE-588)4264758-7 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Terpene |0 (DE-588)4184779-9 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Biosynthese |0 (DE-588)4006902-3 |2 gnd |9 rswk-swf |
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Datensatz im Suchindex
| _version_ | 1804121277019979776 |
|---|---|
| adam_text | THE BIOSYNTHESIS OF
STEROIDS, TERPENES,
AND ACETOGENINS
John H Richards
j California Institute of Technology
I and
i
j James B Hendrickson
Brandeis University
ji !
WABENJAMIN,INC1964
New York Amsterdam
Contents
Preface v
one Introduction 1
1-1 Acetogenins 1
1-2 Biological Isoprene Unit 4
1-3 Polymerization of Isopentenyl Pyrophosphate 6
1-4 Cyclization 8
1-5 Bile Acids and Steroids 9
two Principles of Biogenetic Theory 10
2-1 Data 11
2-2 Functional Group Pattern 11
2-3 Economy 12
2-4 Enzyme Control 13
2-5 Nature of the Reactions 13
2-6 Nature of the Starting Materials 14
2-7 Limitations 14
three Construction of the Acetate Hypothesis 16
3-1 Expansion of the Hypothesis 19
3-2 Summary 26
vii
viii CONTENTS
four Statistical Survey of Natural Compounds 27
4-1 Linear Carbon Skeletons 28
4—2 Phenylpropanoid Skeletons 32
4—3 Acylphloroglucinol Derivatives (Cyclization Path A) 41
4-4 Orsellinic Acid Derivatives (Cyclization Path B) 62
4-5 More Complex Cyclizations 75
4-6 Miscellaneous Compounds 95
4—7 Correlation and Commentary 104
4—8 Alkaloids 116
five Acetogenins: Experimental Verification 121
5-1 Fatty Acids and Other Linear Carbon Skeletons 121
5-2 Aromatic Compounds 140
5-3 Phenylpropanoid and Flavonoid Compounds 155
5-4 Miscellaneous Compounds 164
5-5 Acetate Hypothesis: Final Summary 170
six The Isoprene Unit 173
6-1 Acetate - Mevalonate 175
6-2 Mevalonate Isopentenyl Pyrophosphate 190
6-3 Polymerization of A3-Isopentenyl Pyrophosphate 198
seven Monoterpenes 207
7-1 Acyclic Monoterpenes 207
7-2 Non-Head-to-Tail Monoterpenes 211
7-3 Monocyclic Monoterpenes 213
7-4 Bicyclic Monoterpenes 217
7-5 Cyclopentanoid Monoterpenes 221
eight Sesquiterpenes 225
8-1 Acyclic Sesquiterpenes 225
8-2 Bisabolene 226
8-3 /3-Santalene and Cedrol 227
8-4 Longifolene 229
8-5 Helminthosporal 231
CONTENTS ix
! 8-6 Santonin and Guaiazulene Skeletons 231
i 8-7 Vetivazulenes 235
| 8-8 Eremophilones 236
i 8-9 Sesquiterpenes with Medium-Sized Rings 236
| 8-10 Polygodial and Iresin 237
! 8-11 Trichothecin 238
j nine Diterpenes
I 9-1 Linear Diterpenes 240
j 9-2 Cativic Acid, Sclareol, and Manoöl 241
t 9-3 Pimaranes and Abietanes 243
I 9-4 Phyllocladene-Type Skeletons 244
9-5 Stereochemistry 245
9-6 Diterpenes with Rearranged Skeletons 247
l 9-7 Diterpene Alkaloids 249
I 9-8 Experimental Biosynthetic Results 253
ten Triterpenes 257
10-1 Principles of Reaction Mechanisms 257
10-2 Olefin Cyclizations 259
10-3 Triterpene Rearrangements 263
10—4 Theoretical Postulates 264
10-5 Ambrein (Chair-Chair-Unfolded-Unfolded-Chair) 266
10-6 Onocerin (Chair-Chair-Unfolded-Chair-Chair) 266
10-7 Tetracyclic Triterpenes (Chair-Chair-Chair-Boat-
Unfolded) 267
10-8 Pentacyclic Triterpenes (Chair-Chair-Chair-Boat-
Chair) 268
10-9 Lanosterol (Chair-Boat-Chair-Boat-Unfolded) 273
10-10 Hydroxyhopenone (Chair-Chair-Chair-Chair-Chair) 277
10-11 Alternate Possibilities 277
10-12 Modified Triterpenes 278
10-13 Experimental Evidence for Mechanism of Squalene
Cyclization 280
10-14 Experimental Studies of Triterpene Biosynthesis 285
eleven Higher Terpenoids 289
11-1 Carotenoids 289
11-2 Ubiquinones and Plastoquinones 302
X CONTENTS
twelve Cholesterol Biogenesis 305
12-1 Origin of Carbon Atoms 305
12-2 Conversion of Lanosterol to Cholesterol 311
12-3 Ergosterol 324
thirteen Further Transformations of Cholesterol 326
13-1 Reaction Types 326
13-2 Bile Acids 329
13-3 Corticoids 341
13-4 Androgens 351
13-5 Estrogens 357
13-6 Summary 362
13-7 Steroidal Alkaloids 363
Appendix 365
Index 387
|
| any_adam_object | 1 |
| author | Richards, John H. Hendrickson, James B. |
| author_facet | Richards, John H. Hendrickson, James B. |
| author_role | aut aut |
| author_sort | Richards, John H. |
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| dewey-full | 547.7 |
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| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547.7 |
| dewey-search | 547.7 |
| dewey-sort | 3547.7 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie Biologie |
| format | Book |
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| language | English |
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| spelling | Richards, John H. Verfasser aut The biosynthesis of steroids, terpenes, and acetogenins John H. Richards and James B. Hendrickson New York, NY [u.a.] Benjamin 1964 X, 416 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Frontiers in chemistry Acetates Biochemistry Biosynthesis Steroids Terpenes Polyketide (DE-588)4264758-7 gnd rswk-swf Terpene (DE-588)4184779-9 gnd rswk-swf Biosynthese (DE-588)4006902-3 gnd rswk-swf Steroide (DE-588)4057379-5 gnd rswk-swf Polyketide (DE-588)4264758-7 s Biosynthese (DE-588)4006902-3 s DE-604 Terpene (DE-588)4184779-9 s Steroide (DE-588)4057379-5 s Hendrickson, James B. Verfasser aut HEBIS Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=004513769&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Richards, John H. Hendrickson, James B. The biosynthesis of steroids, terpenes, and acetogenins Acetates Biochemistry Biosynthesis Steroids Terpenes Polyketide (DE-588)4264758-7 gnd Terpene (DE-588)4184779-9 gnd Biosynthese (DE-588)4006902-3 gnd Steroide (DE-588)4057379-5 gnd |
| subject_GND | (DE-588)4264758-7 (DE-588)4184779-9 (DE-588)4006902-3 (DE-588)4057379-5 |
| title | The biosynthesis of steroids, terpenes, and acetogenins |
| title_auth | The biosynthesis of steroids, terpenes, and acetogenins |
| title_exact_search | The biosynthesis of steroids, terpenes, and acetogenins |
| title_full | The biosynthesis of steroids, terpenes, and acetogenins John H. Richards and James B. Hendrickson |
| title_fullStr | The biosynthesis of steroids, terpenes, and acetogenins John H. Richards and James B. Hendrickson |
| title_full_unstemmed | The biosynthesis of steroids, terpenes, and acetogenins John H. Richards and James B. Hendrickson |
| title_short | The biosynthesis of steroids, terpenes, and acetogenins |
| title_sort | the biosynthesis of steroids terpenes and acetogenins |
| topic | Acetates Biochemistry Biosynthesis Steroids Terpenes Polyketide (DE-588)4264758-7 gnd Terpene (DE-588)4184779-9 gnd Biosynthese (DE-588)4006902-3 gnd Steroide (DE-588)4057379-5 gnd |
| topic_facet | Acetates Biochemistry Biosynthesis Steroids Terpenes Polyketide Terpene Biosynthese Steroide |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=004513769&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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