Synthesis of high specific radioactivity 3,5-[3H6]dimethoxy-4-hydroxyacetophenone, an inducing compound of the vir gene in Agrobacterium tumefaciens

Lee, Sungsook; Morimoto, Hiromi; Williams, Philip G.

doi:10.1002/(sici)1099-1344(199706)39:6<461::aid-jlcr992>3.0.co;2-k

Cited by 7 publications

(2 citation statements)

References 21 publications

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“…29 Tritiated methyl iodide (10) from such a procedure was used for the tritiomethylation of 3¢,5¢-dihydroxy-4¢-isopropoxyacetophenone to generate tritiated 3¢,5¢dimethoxy-4¢-isopropoxy-acetophenone (11) (Scheme 7) with S.A. estimated at 73 Ci/mmol (85% of theoretical maximum S.A.). 30 This compound is one of the plant signals that induce the vir genes of Agrobacterium tumefaciens, which causes crown gall tumors on dicotyledonous plants. The tritiated compound was required to aid the identification of the receptors in Agrobacterium tumefaciens to which the plant signal binds, and was consequently required at very high S.A.…”

Section: Methodsmentioning

confidence: 99%

Synthetic Tritium Labeling: Reagents and Methodologies

Saljoughian¹

2002

Synthesis

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This review presents a survey of new high specific activity tritium labeling reagents and methodologies developed in recent years and their applications to tritium labeling chemistry. The review is organized on the basis of reagent type, its development and applications. Emphasis is placed on the synthetic applications of the reagents and techniques that have an exceptionally high capability to produce high specific activity tritium labeled compounds. The focus of this review is on chemical labeling syntheses and does not include heterogeneous/homogeneous metal-catalyzed hydrogentritium exchange and biochemical reactions. 6 Conclusion

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Section: Methodsmentioning

confidence: 99%

Synthetic Tritium Labeling: Reagents and Methodologies

Saljoughian¹

2002

Synthesis

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“…Another application made possible by the availability of LiAlT 4 is the synthesis of tritiated methyl iodide from tritiated methanol, through LiAlT 4 reduction of carbon dioxide [81]. Tritiated methyl iodide from such a procedure was used for the tritiomethylation of 3',5'-dihydroxy-4'-isopropoxyacetophenone to generate tritiated 3',5'-dimethoxy-4'-isopropoxy-acetophenone with specific activity estimated at 73 Ci/mmol (85% of theoretical maximum S.A.) [82]. This compound is one of the plant signals that induce the vir genes of Agrobacterium tumefaciens which causes crown gall tumors on dicotyledonous plants.…”

Section: Lithium Aluminum Tritide (Lialt 4 )mentioning

confidence: 99%

Recent Developments in Tritium Incorporation for Radiotracer Studies

Saljoughian

Williams²

2000

CPD

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The essential nature of rapid radiotracer synthesis very early in drug discovery programs has driven the need for better and more varied tritium incorporation methods. This review presents a summary of recent advances for tritium introduction via tritiated water, tritium gas, complex tritides, and a range of recently improved tritiation reagents. Access to a wider range of tritiated reagents (for tritioacetylation, tritioformylation, methylation, etc.) and commercial manifolds for the transfer and use of tritium gas is also discussed.

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NMR‐based approach to the analysis of radiopharmaceuticals: radiochemical purity, specific activity, and radioactive concentration values by proton and tritium NMR spectroscopy

Schenk

Dormer

Hesk

et al. 2015

Labelled Comp Radiopharmac

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Compounds containing tritium are widely used across the drug discovery and development landscape. These materials are widely utilized because they can be efficiently synthesized and produced at high specific activity. Results from internally calibrated (3)H and (1)H nuclear magnetic resonance (NMR) spectroscopy suggests that at least in some cases, this calibrated approach could supplement or potentially replace radio-high-performance liquid chromatography for radiochemical purity, dilution and scintillation counting for the measurement of radioactivity per volume, and liquid chromatography/mass spectrometry analysis for the determination of specific activity. In summary, the NMR-derived values agreed with those from the standard approaches to within 1% to 9% for solution count and specific activity. Additionally, the NMR-derived values for radiochemical purity deviated by less than 5%. A benefit of this method is that these values may be calculated at the same time that (3)H NMR analysis provides the location and distribution of tritium atoms within the molecule. Presented and discussed here is the application of this method, advantages and disadvantages of the approach, and a rationale for utilizing internally calibrated (1)H and (3)H NMR spectroscopy for specific activity, radioactive concentration, and radiochemical purity whenever acquiring (3)H NMR for tritium location.

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Synthesis of high specific radioactivity 3,5-[3H6]dimethoxy-4-hydroxyacetophenone, an inducing compound of the vir gene in Agrobacterium tumefaciens

Cited by 7 publications

References 21 publications

Synthetic Tritium Labeling: Reagents and Methodologies

Synthetic Tritium Labeling: Reagents and Methodologies

Recent Developments in Tritium Incorporation for Radiotracer Studies

NMR‐based approach to the analysis of radiopharmaceuticals: radiochemical purity, specific activity, and radioactive concentration values by proton and tritium NMR spectroscopy

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