Synthesis of [4-2H2]-, (4R)[4-2H1]- and (4S)[4-2H1]-4-(methylnitrosamino)-1-(3'-pyridyl)-1-butanone, c-4 deuteriated isotopomers of the procarcinogen nnk

Pathak, Tanmaya ; Thomas, Noel F. ; Akhtar, Mahmoud ; Gani, David (1990) Synthesis of [4-2H2]-, (4R)[4-2H1]- and (4S)[4-2H1]-4-(methylnitrosamino)-1-(3'-pyridyl)-1-butanone, c-4 deuteriated isotopomers of the procarcinogen nnk Tetrahedron, 46 (5). pp. 1733-1744. ISSN 0040-4020

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Official URL: http://www.sciencedirect.com/science/article/pii/S...

Related URL: http://dx.doi.org/10.1016/S0040-4020(01)81978-5

Abstract

The synthesis of C-4 dideuteriated and both C-4 monodeuteriated enantiomers of NNK, the metabolic precursor to a variety of potential carcinogens, starting from (2S)-glutamic acid and nicotinic acid is described. The route is suitable for the synthesis of NNK isotopomers labelled in each of the putative sites for metabolic activation.

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