The organic chemistry of isotopic labelling:
Gespeichert in:
| 1. Verfasser: | |
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| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Cambridge
RSC Publ.
2011
|
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | Literaturverz. S. 149 - 160 |
| Beschreibung: | XV, 184 S. graph. Darst. 24 cm |
| ISBN: | 9781849731881 1849731888 |
Internformat
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Datensatz im Suchindex
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| adam_text | Titel: The organic chemistry of isotopic labelling
Autor: Hanson, James Ralph
Jahr: 2011
Contents
An Introduction to the Organic Chemistry of Isotopic Labelling xiii
Chapter 1 The Discovery and Detection of Isotopes 1
1.1 Introduction 1
1.2 The Discovery of Isotopes 2
1.3 Early Applications of Isotopically Labelled
Compounds 5
1.4 The Selection of an Isotopic Label 9
1.5 The Detection of Isotopes 13
1.6 Nomenclature 18
Chapter 2 Labelling Compounds with Carbon-13 and Carbon-14 20
2.1 Introduction 20
2.2 Carbon Labelling Using the Cyanide Ion 21
2.3 Organometallic Reagents in Carbon Labelling 24
2.4 The Wittig Reaction in Carbon Labelling 27
2.5 Carbonyl Condensation Reactions in Carbon
Labelling 28
2.6 The Synthesis of Carbon-labelled Mevalonic Acid 31
2.7 Aromatic Compounds Labelled in the Ring 33
2.8 Ring-labelled Heterocyclic Compounds 35
2.9 Biosynthetic Methods of Carbon Labelling 38
Chapter 3 Labelling with Deuterium and Tritium 40
3.1 Introduction 40
3.2 The Kinetic Isotope Effect 41
3.3 The Isolation of Deuterium and Tritium 42
The Organic Chemistry of Isotopic Labelling
By James R. Hanson
© James R. Hanson 2011
Pubiished by the Royal Society of Chemistry, www.rsc.org
ix
x Contents
3.4 Exchange Reactions in Deuterium and Tritium
Labelling 43
3.4.1 Heteroatom X-H Exchange Reactions 44
3.4.2 General C-H Exchange Reactions 44
3.4.3 Site-specific C-H Exchange Reactions 45
3.4.4 Exchange Reactions of Carbonyl Compounds 49
3.4.5 Exchange Reactions in the Preparation of
Some Deuteriated Solvents 51
3.5 Decarboxylation Reactions in Deuterium and Tritium
Labelling 51
3.6 Reduction Reactions 52
3.6.1 Reducing Agents 52
3.6.2 The Reduction of Carbonyl Groups 54
3.6.3 The Hydrogenolysis of Aliphatic Substituents 54
3.6.4 The Catalytic Reduction of Alkenes and
Alkynes 54
3.6.5 The Hydrogenolysis of Aryl Halides 56
3.6.6 The Reduction of Iminium Salts 58
3.6.7 The Hydrogenolysis of Organometallic
Compounds 58
3.6.8 Hydroboration 59
3.7 Deuterium- and Tritium-labelled Alkyl Halides 60
Chapter 4 Stereochemical Aspects of Labelling with Hydrogen
Isotopes 62
4.1 Introduction 62
4.2 The Application of the Cahn-Ingold-Prelog
Sequence Rules to Labelled Compounds 63
4.3 The Stereochemistry of Reactions Used in Labelling 64
4.4 Labelled Steroids 69
4.5 Labelled Gibberellin Plant Hormones 73
4.6 The Chiral Methyl Group 75
4.7 Stereospeciflcally Labelled Mevalonic Acid 78
4.8 Stereospeciflcally Labelled Isopentenyl Diphosphate 81
4.9 Labelling of 1-Deoxy-D-xylulose 83
4.10 The Stereochemistry of Hydrogen Transfer from the
Nicotinamide Coenzymes 84
Chapter 5 The Synthesis of Labelled Amino Acids 86
5.1 Introduction 86
5.2 The Synthesis of Racemic Labelled Amino Acids 87
5.3 Labelled Enantiopure Amino Acids 89
Contents
XI
Chapter 6 The Labelling of Some Compounds of Pharmaceutical
Interest
96
6.1 Introduction
6.2 Lidocaine
6.3 Non-steroidal Anti-infiammatory Agents
6.4 Amphetamines
6.5 Sulfonamides
6.6 Morphine and Its Relatives
6.7 Galanthamine
6.8 Tropane Alkaloids
6.9 Tryptamine Derivatives
96
97
98
101
102
103
106
107
108
Chapter 7 Labelling Compounds with the Stable Isotopes of Nitrogen
and Oxygen
110
7.1 Nitrogen-15
7.2 Oxygen-17 and Oxygen-18
110
116
Chapter 8 Labelling with Isotopes of Phosphorus, Sulfur and the
Halogens
122
8.1 Phosphorus-32
8.2 Sulfur-34 and Sulfur-35
8.3 Chlorine-36
8.4 Iodine Isotopes
122
124
126
126
Chapter 9 Labelling Organic Compounds for Diagnostic Imaging
129
9.1 Introduction 129
9.2 Positron Emission Tomography 129
9.3 Carbon-11 in PET 131
9.4 Fluorine-18 in PET 135
9.5 Nitrogen-13 in PET 141
9.6 Oxygen-15 in PET 141
9.7 Isotopes of Bromine 141
9.8 Positron-emitting Metallic Isotopes in PET 142
9.9 Single Photon Emission Computed Tomography 143
9.10 Technetium-99m 143
9.11 Iodine-123 144
Conclusion 146
Further reading 149
xii Contents
Glossary 161
Appendix 167
Subject Index 172
|
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| illustrated | Illustrated |
| indexdate | 2024-07-10T00:40:13Z |
| institution | BVB |
| isbn | 9781849731881 1849731888 |
| language | English |
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| physical | XV, 184 S. graph. Darst. 24 cm |
| publishDate | 2011 |
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| spelling | Hanson, James R. Verfasser aut The organic chemistry of isotopic labelling James R. Hanson Cambridge RSC Publ. 2011 XV, 184 S. graph. Darst. 24 cm txt rdacontent n rdamedia nc rdacarrier Literaturverz. S. 149 - 160 Isotopenmarkierung (DE-588)4176811-5 gnd rswk-swf Organische Synthese (DE-588)4075695-6 gnd rswk-swf Radiolabeling. Isotopenmarkierung (DE-588)4176811-5 s Organische Synthese (DE-588)4075695-6 s TUWSMU HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=026103941&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Hanson, James R. The organic chemistry of isotopic labelling Isotopenmarkierung (DE-588)4176811-5 gnd Organische Synthese (DE-588)4075695-6 gnd |
| subject_GND | (DE-588)4176811-5 (DE-588)4075695-6 |
| title | The organic chemistry of isotopic labelling |
| title_auth | The organic chemistry of isotopic labelling |
| title_exact_search | The organic chemistry of isotopic labelling |
| title_full | The organic chemistry of isotopic labelling James R. Hanson |
| title_fullStr | The organic chemistry of isotopic labelling James R. Hanson |
| title_full_unstemmed | The organic chemistry of isotopic labelling James R. Hanson |
| title_short | The organic chemistry of isotopic labelling |
| title_sort | the organic chemistry of isotopic labelling |
| topic | Isotopenmarkierung (DE-588)4176811-5 gnd Organische Synthese (DE-588)4075695-6 gnd |
| topic_facet | Isotopenmarkierung Organische Synthese |
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