Preparation of Compounds Labeled with Tritium and Carbon-14

Name: Preparation of Compounds Labeled with Tritium and Carbon-14
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Rolf Voges J. Richard Heys Thomas Moenius(Autor*in)

Wiley (Verlag)

Erschienen am 16. März 2009

682 Seiten

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Rolf Voges studied chemistry at the Universities of Marburgand Freiburg, where he received his Ph.D. in organic chemistry oninvestigations into steric isotope effects, for which he receivedthe Go¨deke Award. After postdoctoral research onstereoselective syntheses he joined the isotope group of SandozPharma AG (now Novartis AG) being involved for thirty years inorganic radiochemical synthesis as Head of the Isotope Laboratoriesand then Head of Isotope Section. He is author or coauthor of about40 publications, one patent, and coeditor of two previousconference proceeding volumes in the field, co-organizer of twointernational symposia on the synthesis and application ofisotopically labeled compounds, founder and co-organizer of elevenBad Soden meetings of the Central European Division of theInternational Isotope Society (CED-IIS), and co-editor of theproceedings. For three years he held a leadership position in theIIS, serving as its 2001 president. In recognition of hisscientific achievements and his service to the isotope society hereceived the IIS-CED Award in 1995 and in 2003 the IISAward. He isnow retired and lives in southwestern Germany, near the Swiss andFrench borders.
Richard Heys received his Ph.D. in organic chemistry fromStanford University in 1976 and conducted postdoctoral research inthe chemistry department at Yale; both involved the synthesis ofradiolabeled compounds and their use in elucidation of biosyntheticpathways. His subsequent 29-year career in organic radiochemicalsynthesis both in the laboratory and as a manager took him to theRadiochemistry Department of Midwest Research Institute (now partof Aptuit, Inc.), Smith Kline & French Laboratories/SmithKlineBeecham Pharmaceuticals (now GlaxoSmithKline) and AstraZenecaPharmaceuticals. Author or coauthor of over 85 publications, 8patents and a previous conference proceedings volume in the field,organizer of an international symposium on the synthesis ofisotopically labeled compound and holder of leadership positions(including president and CFO) in the International Isotope Societyfor 9 years, he is retired and lives in northwesternConnecticut.
Thomas Moenius received his Ph.D. in organic chemistryfrom the University of Erlangen-Nu¨rnberg in 1986. He is amember of the isotope group of Novartis Pharma AG, working in thefield of carbon-14 and tritium labeling. Since 2007 he is alsoEuropean Editor for Journal for Labelled Compounds andRadiopharmaceuticals.

Autor*in

Rolf Voges

J. Richard Heys

Thomas Moenius

Novartis Pharma

Inhalt

Preface.
Glossary.
Author Biographies.
1 Introduction.
1.1 Physical Properties of Tritium and Carbon-14.
1.2 Purification.
1.3 Analysis.
1.4 Stability and Storage of Compounds Labeled with Tritium or Carbon-14.
1.5 Specialist Techniques and Equipment.
References 21.
2 Strategies for Target Preparation.
2.1 Formulating Target Specifications.
2.2 Planning Radiotracer Preparations.
References.
3 Preparation of Tritium-Labeled Compounds by Isotope Exchange Reactions.
3.1 Homogeneous Acid- or Base-Catalyzed Exchange.
3.2 Heterogeneous Catalysis with Tritium in Solvent.
3.3 Heterogeneous Catalysis in Solution with Tritium Gas.
3.4 Homogeneous Catalysis in Solution with Tritiated Water.
3.5 Homogeneous Catalysis with Tritium Gas.
3.6 Solvent-Free Catalytic Exchange.
References.
4 Preparation of Tritium-Labeled Compounds by Chemical Synthesis.
4.1 Catalytic Tritiations.
4.2 Catalytic Tritiolyses.
4.3 Tritide Reductions.
4.4 Small Tritiated Building Blocks.
References.
5 Barium [14C]Carbonate and the Preparation of Carbon-14-Labeled Compounds via One-Carbon Building Blocks of the [14C]Carbon Dioxide Tree.
5.1 [14C]Carbon Dioxide (14CO2).
5.2 [14C]Carbon Monoxide (14CO).
5.3 [14C]Formic Acid (H14COOH).
5.4 [14C]Formaldehyde (H14CHO).
5.5 [14C]Methyl Iodide (14CH3I).
5.6 [14C]Nitromethane (14CH3NO2).
References.
6 Preparation of Carbon-14-Labeled Compounds via Multi-Carbon Building Blocks of the [14C]Carbon Dioxide Tree.
6.1 [14C]Acetic Acid and Its Derivatives.
6.2 Halo[14C]acetates.
6.3 [14C]Acetone.
6.4 Alkyl [14C]Acetoacetate.
6.5 [14C]Malonates.
References.
7 Preparation of Carbon-14-Labeled Compounds via the [14C]Cyanide Tree.
7.1 Metal [14C]Cyanides.
7.2 Preparation of Other Building Blocks from [14C]Cyanide.
References.
8 Preparation of Carbon-14-Labeled Compounds via the [14C2]Acetylene Tree.
8.1 [14C2]Acetylene (H14C:14CH).
8.2 [14C2]Acetaldehyde (14CH3 14CHO).
8.3 [1,2-14C2]Acetic Acid (14CH3 14COOH).
8.4 2-[2,3-14C2]Propyne-1-ol ([2,3-14C2]Propargyl Alcohol) and 2-[2,3-14C2]Butyne-1,4-diol.
8.5 Methyl [2,3-14C2]Propiolate (H14C_14CCOOMe) and Dimethyl [2,3-14C2]Acetylenedicarboxylate (HOOC14C_14CCOOH).
8.6 1,2-[14C2]Dibromoethane (Br14CH2 14CH2Br).
8.7 [14C2]Ethylene Oxide.
8.8 [14Cn]Benzene and the Synthesis of Ring-Labeled Aromatic Compounds.
References.
9 Preparation of Carbon-14-Labeled Compounds via the [14C]Cyanamide Tree.
9.1 [14C]Cyanamide (H2N14C_N).
9.2 [14C]Guanidine (H2N14C(¼NH)NH2).
9.3 [14C]Urea, H2N14CONH2.
9.4 [14C]Thiourea, H2N14CSNH2 .
References.
10 Reconstitution Strategies.
10.1 Replacement Strategies.
10.2 Disconnection-Reconnection Strategies.
References.
11 Preparation of Enantiomerically Pure Compounds Labeled with Isotopes of Hydrogen and Carbon.
11.1 Resolution of Racemates.
11.2 Enantioselective Synthetic Methods.
11.3 Diastereoselective Synthetic Procedures.
References.
12 Biotransformations in the Preparation of Compounds Labeled with Carbon and Hydrogen Isotopes.
12.1 Applications of Isolated Enzymes.
12.2 Application of Cell-Containing Systems.
12.3 Biocatalyzed Synthesis of Key Intermediates for Reconstitution Approaches.
References.
Index.

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