330808-45-2Relevant academic research and scientific papers
Preparation of (all-E)- and (11Z)-12-haloretinals and (11Z,13Z)- and (13Z)-14-haloretinals by the C15 + C5 route - Exploring the possibility of preparing any retinoid rationally chemically modified at any position in the conjugated t
Wang, Yajie,Lugtenburg, Johan
, p. 5100 - 5110 (2007/10/03)
In this paper we describe how chemically modified ylides can be prepared by electrophilic substitution in a simple way. A subsequent Horner-Emmons reaction gives access to (all-E)- and (HZ)-12-chloro-, -12-bromo-, and -12-iodoretinal. It could be expected
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.
