16651-05-1Relevant academic research and scientific papers
Gb3 Glycosphingolipids with Fluorescent Oligoene Fatty Acids: Synthesis and Phase Behavior in Model Membranes
Patalag, Lukas J.,Sibold, Jeremias,Schütte, Ole M.,Steinem, Claudia,Werz, Daniel B.
, p. 2171 - 2178 (2017/10/07)
Glycosphingolipids are involved in a number of physiological and pathophysiological processes, and they serve as receptors for a variety of bacterial toxins and viruses. To investigate their function in lipid membranes, fluorescently labeled glycosphingolipids are highly desirable. Herein, a synthetic route to access Gb3 glycosphingolipids with fluorescently labeled fatty acids, consisting of pentaene and hexaene moieties either at the terminus or in the middle of the acyl chain, has been developed. The fluorescent properties of the Gb3 derivatives were investigated in small unilamellar vesicles composed of a raft-like mixture. Phase-separated giant unilamellar vesicles (GUVs) allowed the quantification of the apparent partitioning coefficients of the Gb3 compounds by means of confocal fluorescence laser scanning microscopy. The determined partition coefficients demonstrate that the Gb3 derivatives are preferentially localized in the liquid-disordered (ld) phase. To analyze whether the compounds behave like their physiological counterparts, Cy3-labeled (Cy: cyanine) Shiga toxin B subunits (STxB) were specifically bound to Gb3-doped GUVs. However, the protein was favorably localized in the ld phase, in contrast to results reported for STxB bound to naturally occurring Gb3, which is discussed in terms of the packing density of the lipids in the liquid-ordered (lo) phase.
Four- and eight-carbon homologation of benzaldehyde by (1Z,3Z)- butyltelluro-1,3-butadiene: Synthesis of navenone B: Alarm pheromone of the mollusk navanax inermis
Dabdoub, Miguel J.,Dabdoub, Vania B.,Baroni, Adriano C.M.,Barbosa, Sandro L.
, p. 942 - 950 (2012/02/01)
Four- and eight-carbon homologation of benzaldehydes is described. The hydrotel-luration of (Z)-1-methoxy-but-1-en-3-ynes 1 afforded (1Z,3Z)-1-butyltelluro-4-methoxy-1,3-butadiene 2, this compound 2 underwent a Te=Li exchange reaction, and the butadienyl-lithium 3 obtained reacted with benzaldehyde to form the corresponding allylic alcohol 4 with total retention of configuration. The allylic alcohol 4a formed underwent acidic hydrolysis, resulting in 5-phenyl-(2E,4E)-dienal 5 (four-carbon homologation of benzaldehyde). Product 5 reacted with the butadienyllithium 3, affording the alcohol 9-phenyl-(1-Z,3Z,6E,8E)-1-methoxy-5-hydroxy-nonatetraene 6, which was hydrolyzed or spontaneously transformed into 9-phenyl-(2E,4E,6E,8E)-tetraenal 7, completing the eight-carbon homologation of benzaldehyde. Reaction of 9-phenyl-nona-(2E,4E,6E,8E)-tetraenal 7 with methyllithium in tetrahydrofuran afforded (3E,5E,7E, 9E)-10-phenyl-deca-3,5,7,9-tetraen-2-ol 8. The product of the reaction described was employed in the synthesis of (3E,5E,7E,9E)-10-phenyl- deca-3,5,7,9-tetraen-2-one 9, which is known as navenone B, an alarm pheromone of the mollusk Navanax inermis. Taylor & Francis Group, LLC.
Acidic ionic liquid-catalyzed homologation of the polyene chain in α,β-enals (polyenals)
Kryshtal, Galina V.,Zhdankina, Galina M.,Ignat'Ev, Nikolai V.,Schulte, Michael,Zlotin, Sergei G.
experimental part, p. 173 - 178 (2011/02/27)
An efficient green-chemistry synthesis of conjugated polyenals from α,β-enals, orthoesters, and alkyl vinyl ethers promoted by acidic ionic liquid [emim][HSO4] is described. The ionic liquid can be reused at least three times without any decrease in product yields.
ω-Halogeno polyenals: Preparation and application to a one-pot synthesis of polyenals from carbonyl compounds
Soullez, David,Ple, Gerard,Duhamel, Lucette
, p. 1639 - 1645 (2007/10/03)
Syntheses of 5-halogeno-2,4-dienals 1a-c are described starting either from the glutaconaldehyde potassium salt or from furan. The 5-bromopenta-2,4-dienal 1b can be transformed efficiently into homologous ω-bromo polyenals 2-4, precursors of ω-bromo polye
Reactivity of polyvinylogation: Easy and rapid access to different polyenals
Ramondenc,Ple
, p. 10855 - 10876 (2007/10/02)
This work describes the synthesis and the reactivity of three reagents of polyvinylogation 1-3. By condensation with several aldehydes and ketones, these reagents allow the introduction of three or four doubles bonds, leading to polyenals 5-6 in one or tw
A Simple and Highly Stereoselective Route to E-α,β-Unsaturated Aldehydes
Bellassoued, Moncef,Majidi, Assieh
, p. 2517 - 2522 (2007/10/02)
Zinc bromide mediated reaction of α,α-bis(trimethylsilyl)-tert-butylacetaldimine (3) with a wide range of aldehydes takes place under mild conditions and affords the corresponding α,β-unsaturated aldehydes in good yields and with high E stereoselectivity (>98percent).This procedure is successfully applied to the preparation of intermediates for retinoid and natural product synthesis.
