87355-35-9Relevant academic research and scientific papers
Simple and efficient preparation of [10,20-13C2]- and [10-CH3,13-13C2]-10-methylretinal: Introduction of substituents at the 2-position of 2,3-unsaturated nitriles
Verdegem,Monnee,Lugtenburg
, p. 1269 - 1282 (2007/10/03)
In this paper, we present the synthesis of [10,20-13C2]-10-methylretinal and [10-CH3,13-13C2]-10-methylretinal, two doubly 13C-labeled chemically modified retinals that have been recently used to study the structural and functional details behind the photocascade of bovine rhodopsin (Verdegem et al. Biochemistry 1999, 38, 11316; de Lange et al. Biochemistry 1998, 37, 1411). To obtain both doubly 13C-labeled compounds, we developed a novel synthetic method to directly and regiospecifically introduce a methyl substituent on the 2-position of 3-methyl-5-(2′,6′,6′-trimethyl-1′ -cyclohexen-1′-yl)-2,4-pentadienenitrile. Encouraged by these results, we investigated the scope of this novel reaction by developing a general method for the introduction of a variety of substituents to the 2-position of 3-methyl-2,3-unsaturated nitriles, paving the way for simple and efficient synthesis of a wide variety of 10-, 14-, and 10,14-substituted chemically modified retinals, and other biologically important compounds.
Synthesis of 10-, 11-, 19- and 20-mono-13C-retinal
Pardoen, J. A.,Neijenesch, H. N.,Mulder, P. P. J.,Lugtenburg, J.
, p. 341 - 347 (2007/10/02)
The 10-, 11-, 19- and 20-mono-13C-all-trans-retinals were synthesized with >98percent chemical purity and 92percent 13C incorporation from 13C-labelled acetonitrile and 13C-labelled methyl iodide.Their 13C-13C and 13C-1H NMR coupling constants were measur
