Preparation of Compounds Labeled with Tritium and Carbon-14

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 .

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 [¹⁴C_n]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=NH)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.