90972-59-1Relevant articles and documents
Comparative analysis of the olfactory properties of silicon/germanium/tin analogues of the lily-of-the-valley odorants lilial and bourgeonal
D?rrich, Steffen,Gelis, Lian,Wolf, Steffen,Sunderk?tter, Astrid,Mahler, Christoph,Guschina, Elena,Tacke, Reinhold,Hatt, Hanns,Kraft, Philip
, p. 1747 - 1752 (2014)
The silicon/germanium/tin analogues of the lily-of-the-valley odorants lilial (rac-1a), compounds rac-1b, rac-1c, and rac-1d, and bourgeonal (2a), compounds 2b, 2c, and 2d, were synthesized and characterized for their olfactory properties, including GC-olfactometry studies. Compounds rac-1a-c and 2a-c possess a typical lily-of-the-valley odor, whereas the stanna-analogues rac-1d and 2d, despite some floral aspects, clearly no longer belong to the lily-of-the-valley family. In both series of the carbon/silicon/germanium/tin analogues studied, the lily-of-the-valley odor decreases in the order of carbon2+ imaging. Bourgeonal (2a) showed the highest activation potency, whereas lilial (rac-1a) and sila-bourgeonal (2b) exhibited lower activation potencies. Sila-lilial (rac-1b), germa-lilial (rac-1c), and stanna-lilial (rac-1d), as well as germabourgeonal (2c) and stanna-bourgeonal (2d), did not activate heterologously expressed hOR17-4 at the concentrations tested. The carbon/silicon/germanium/tin switch strategy thus showed that the stanna-derivatives clearly exceeded the molecular dimensions of the odorant receptor(s) responsible for the recognition of lily-of-the-valley odorants, although the receptor affinity was already affected with the sila- and germaanalogues. These data could later be used in the qualitative and quantitative evaluation of computational receptor models.
