25109-57-3Relevant articles and documents
Three bacteriorhodopsins with ring-didemethylated 6-s-locked chromophores and their properties
Groesbeek, M.,Galen, A. J. J. van,Ippel, J. H.,Berden, J. A.,Lugtenburg, J.
, p. 237 - 246 (2007/10/02)
Three novel, 6-s-locked rigidified retinals, racemic all-E 1,5-didemethyl-8,16-methanoretinal, all-E, 1,1-didemethyl-8,18-methanoretinal and all-E 8a,18-didehydro-1,1-didemethyl-8,18-methanoretinal were prepared in good yield in high purity on a 100-mg scale.For the preparation of the key intermediate in the synthesis of 1,5-didemethyl-8,16-methanoretinal, reductive cyanation of an unsaturated cyanohydrin to the corresponding conjugated nitrile was accomplished using triethylsilane and trifluoroacetic acid.The three locked retinals interact with bacterioopsin to form bacteriorhodopsin with about the same rate as the native chromophore.This work proves that steric interaction of the 1,1-dimethyl group in the chromophore is an important factor in binding to bacterioopsin.
Monoozonolyses of Acyclic Conjugated Dienes
Griesbaum, Karl,Zwick, Gerhard
, p. 3041 - 3057 (2007/10/02)
Monoozonolyses of isoprene (1a), 2-methyl-3-phenyl-1,3-butadiene (1b), 2,3-diphenyl-1,3-butadiene (25), and 2,3,4,5-tetramethyl-2,4-hexadiene (34) have been examined in pentane and in methanol.The dienes 1a, b and 25 afforded all possible α,β-unsaturated monoozonides and α,β-unsaturated methoxy hydroperoxides, respectively, whereas diene 34 gave no ozonide and no α,β-unsaturated methoxy hydroperoxide.From the dienens 25 and 34, the corresponding monoepoxides have been formed additionally.The results allow some conclusions concerning the regioselectivity of ozone attack at the unsymmetrically substituted dienes 1a, b as well as concerning the cleavage directions of primary ozonides.