33598-78-6Relevant articles and documents
Synthesis of 15N labelled isophosphoramide mustard
Shulman-Roskes,Gamcsik,Golvin,Chang,Koo,Ludeman
, p. 231 - 237 (1994)
The ifosfamide metabolite isophosphoramide mustard (IPM) was synthesized with isotopic enrichment at each nitrogen site. Glycine-15N was converted to 2-chloroethylamine-15N hydrochloride (4 steps, 21% net yield) which was then reacte
COMPOUND, DIAGNOSTIC AGENT, NUCLEAR MAGNETIC RESONANCE ANALYSIS METHOD, NUCLEAR MAGNETIC RESONANCE IMAGING METHOD, MASS SPECTROMETRY METHOD AND MASS SPECTROMETRY IMAGING METHOD
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Page/Page column 28; 29, (2009/04/25)
To produce a labeled compound for a selected biological substance not using a radioisotope atom which has a risk of exposure to radioactivity and limitation on handling time but using a stable isotope atom; and that the labeled compound can be measured with good sensitivity separably from naturally occurring compounds of the selected biological substance which are substituted with the stable isotope atom. Choline as a biological substance is labeled by substituting the nitrogen atom of the quaternary ammonium group and all the carbon atoms of the methyl group attached to the nitrogen atom with respective isotopes 15N and 13C and used as a diagnostic agent.
Hydrolysis of phosphotriesters: Determination of transition states in parallel reactions by heavy-atom isotope effects
Anderson,Shim,Raushel,Cleland
, p. 9246 - 9253 (2007/10/03)
The remote label method was used to measure primary and secondary 18O isotope effects in the alkaline hydrolysis of O,O-diethylphosphorylcholine iodide (DEPC) and the primary 18O effect in the alkaline hydrolysis of O,O-diethyl-m-nitrobenzyl phosphate (DEmNBP). Both the leaving group of interest (choline or m-nitrobenzyl alcohol) and ethanol can be ejected during hydrolysis due to the similarity of their pK values. The heavy-atom isotope effects were measured by isotope ratio mass spectrometry. Parallel reaction and incomplete labeling corrections were made for both systems. DEPC has a primary 18O isotope effect of 1.041 ± 0.003 and a secondary 18O isotope effect of 1.033 ± 0.002. The primary 18O isotope effect for DEmNBP was 1.052 ± 0.003. These large effects suggest a highly associative transition state in which the nucleophile approaches very close to the phosphorus atom to eject the leaving group. The large values are also indicative of a large compression, or general movement, on the reaction coordinate.