[structure: see text] The synthesis of p-octiphenyls carrying orthogonal tert-butyl esters in the peripheral positions 1(2), 2(2), 3(3), 6(2), 7(3), and 8(2) and either p-methoxybenzyl or benzyl ester substituents in the central positions 4(2) and 5(3) is described. Resolution-enhanced HSQC/HMBC two-dimensional NMR spectroscopy is implemented as an attractive method for the complete characterization of complex p-oligophenyl scaffolds.
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Synthesis of [323]-p-octiphenyls: orthogonal functionalization along a rigid-rod scaffold for refined supramolecular architecture.
Org Lett
March 2004
Department of Organic Chemistry, University of Geneva, Geneva, Switzerland.
[structure: see text] The synthesis of p-octiphenyls carrying orthogonal tert-butyl esters in the peripheral positions 1(2), 2(2), 3(3), 6(2), 7(3), and 8(2) and either p-methoxybenzyl or benzyl ester substituents in the central positions 4(2) and 5(3) is described. Resolution-enhanced HSQC/HMBC two-dimensional NMR spectroscopy is implemented as an attractive method for the complete characterization of complex p-oligophenyl scaffolds.
View Article and Find Full Text PDFVoltage-dependent formation of anion channels by synthetic rigid-rod push-pull beta-barrels.
Chemistry
January 2003
Department of Organic Chemistry, University of Geneva, 1211 Geneva 4, Switzerland.
Article Synopsis
- Researchers studied ion channels made from p-octiphenyls with amphiphilic, cationic tripeptide strands, examining two versions: one with an axial dipole moment (5) and one without (6).
- The channels exhibited voltage dependence and anion selectivity in fluorescence tests and conductance measurements, with 5 forming short-lived channels that could transition into stable structures.
- Studies confirmed that membrane potentials influenced the ability of compound 5 to integrate into bilayers, suggesting that this integration is dependent on voltage.
Toward catalytic rigid-rod beta-barrels: a hexamer with multiple histidines.
Chirality
January 2002
Department of Organic Chemistry, University of Geneva, Geneva, Switzerland.
Rigid-rod beta-barrels are composed of interdigitating, short, amphiphilic peptide strands that are flanked by stabilizing rigid-rod "staves." As a first step toward the construction of catalytic rigid-rod beta-barrels, we here report synthesis and study of a new barrel designed to comprise alternating leucine and histidine residues at the inner and lysine and glutamate residues at the outer barrel surface. Synthesis of p-octiphenyls with lateral tripeptide strands followed procedures described previously.
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