title: Isotope-labeling of the fibril binding compound FSB via a Pd-catalyzed double alkoxycarbonylation.
abstract: We have synthesized two isotopically labeled variants of the β-amyloid binding compound FSB possessing (13)C-labels on the two terminal aryl carboxylic acid moieties. One of these was also fully deuterated on the olefinic spacers. The (13)C-isotope labeling was achieved applying a Pd-catalyzed methoxycarbonylation of the corresponding aryl chlorides with externally (ex situ) generated (13)C-labeled CO. Application of the Shirakawa-Hayashi protocol for the Pd-catalyzed reduction of a dialkyne intermediate using D(2)O allowed for the selective deuterium labeling of the two trans-C,C double bonds of FSB.
authors.affiliation: Center for Insoluble Protein Structures, Department of Chemistry and Interdisciplinary Nanoscience Center, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark.
authors.forename: Mia N
authors.initials: MN
authors.lastname: Burhardt
authors.forename: Rolf
authors.initials: R
authors.lastname: Taaning
authors.forename: Niels Chr
authors.initials: NC
authors.lastname: Nielsen
authors.forename: Troels
authors.initials: T
authors.lastname: Skrydstrup
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D000682:Amyloid / Q000737:chemistry*; D002384:Catalysis; D007553:Isotope Labeling / Q000379:methods*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011485:Protein Binding; D050050:Protein Carbonylation
chemical_list: D000480:Alkynes; D000682:Amyloid; D010165:Palladium