Preparation tritium-labeled

Gabriel and Ashwell463 prepared tritium-labeled sucrose and a-D-[3-3H]-allopyranosyl /i-1)-fructofuranoside by reduction of a-D-rzZw-hexopyranosyl-3-ulose /i-D-fruetoluranoside ( 3-ketosucrose, 247) with tritiated borohydride. 

A method for preparing tritium-labelled oligosaccharides of hyaluronic acid has used the Wilzbach recoil technique the tritiated oligosaccharides are of potential use in studies of the mechanism of hyaluronidases. A four-fold helical form of hyaluronic acid has been detected using the data from fibre-... 

Figure 2.14 Use of a multistep disconnection/reconnection strategy for preparing tritium-labeled paclitaxel...

The introduction of tritium into molecules is most commonly achieved by reductive methods, including catalytic reduction by tritium gas, PH2], of olefins, catalytic reductive replacement of halogen (Cl, Br, or I) by H2, and metal pH] hydride reduction of carbonyl compounds, eg, ketones (qv) and some esters, to tritium-labeled alcohols (5). The use of tritium-labeled building blocks, eg, pH] methyl iodide and pH]-acetic anhydride, is an alternative route to the preparation of high specific activity, tritium-labeled compounds. The use of these techniques for the synthesis of radiolabeled receptor ligands, ie, dmgs and dmg analogues, has been described ia detail ia the Hterature (6,7). 

Epoxyfarnesol was first prepared by van Tamelen, Stomi, Hessler, and Schwartz 4 using essentially this procedure. It is based on the findings of van Tamelen and Curphey5 that N-bromosuccinimide in a polar solvent was a considerably more selective oxidant than others they tried. This method has been applied to produce terminally epoxidized mono-, sesqui-, di-, and triterpene systems for biosynthetic studies and bioorganic synthesis.6 It has also been applied successfully in a simple synthesis of tritium-labeled squalene [2,6,10,14,18,22-Tetracosahexaene, 2,6,10,15,19,23-hexamethyl-, (all-E)-] and squalene-2,3-oxide [Oxirane, 2,2-dimethyl-3-(3,7,12,16,20-pentamethyl-3,7,ll,-15,19-heneicosapentaenyl)-, (all-E)-],7 and in the synthesis of Cecropia juvenile hormone.8... 

Preparation of Tritium-Labeled Dibenzo- -dioxin and 2,3,7,8-Tetrachlorodibenzo-//-dioxin... 

Muelder and Shadoff (3) prepared C-2,3,7,8-Cl4-DBpD (0.9 mCi/ mmole) by chlorination of C-2,7-dichlorodibenzo-p-dioxin made from potassium C-2,4-dichlorophenate. The preparation of tritium-labeled 2,3,7,8-Cl4-DBpD is justified because the radiolabeled intermediates are less expensive and more accessible and because a higher specific activity is potentially attainable. Here, we consider the optimal conditions for the reaction sequence designed to obtain products of high chemical and radiochemical purity shown at the top of p. 8. 

A thiazole core has also been utilised by Solvay Pharmaceuticals [309] in the search for a novel bioisosterie replacement of the rimonabant (382) pyrazole core. The affinity of several compounds for the human CBi receptor was determined in transfected CHO cells using tritium-labelled CP 55940. Antagonism was determined in the same cell line by WIN 55212-2-induced release of arachidonic acid. The pK[ of (456) was found to be 6.9, while the p 2 value was measured as 8.7. A series of six 1,2,4-triazole analogues has been prepared by Jagerovic et al. [310], via their corresponding A-acylbenzamides (Table 6.39). 

This tritiated water can become incorporated into the normal bases of DNA and may contribute significantly to the overall apparent binding levels measured in DNA (4). Such problems are circumvented in the case of 14C labeled hydrocarbons. Tritium labeled compounds can be prepared at sufficiently high specific activities (often 20-80 Ci/mmole) that fentomole amounts of adduct may be detected. 

In the preparation of tritium-labeled compounds there are four stages ... 

This photoaffinity labelling analogue of all-fraws-retinal, 95b, has been tritium labelled80 by reduction of unlabelled aldehyde 95a with [3H]-NaBH4 and subsequent oxidation of the obtained tritium-labelled retinol with activated manganese dioxide. The product 95b (specific activity 38.3 mCimmol-1) has been isolated by preparative TLC (equation 36). 

The tritium labelled V.fischeri AHL 31 was prepared with a specific activity of 45-55 Ci/mmol by the tritiation of the corresponding unsaturated precursor, AT-(3-oxo-4-hexenoyl)-L-HSL 30 in the presence of a homogeneous Wilkinson s catalyst, tris(triphenylphosphine)rhodium[I] chloride (Scheme 13) [71]. 

Quite recently, tritium-labelled LY186126 (25), a compound that mimics indolidan pharmacologically and biochemically as well, has been prepared as a tool for studying the binding site for PDE-inhibitor cardiotonics... 

Tritium-labelled veratridine (35) has been prepared, with high specific activity, by condensation of veracevine with 3-bromo-4,5-dimethoxybenzoyl chloride followed by catalytic reduction with tritium gas.79... 

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