Isotope-labeling of the fibril binding compound FSB via a Pd-catalyzed double alkoxycarbonylation.

Autor: Burhardt MN; Center for Insoluble Protein Structures, Department of Chemistry and Interdisciplinary Nanoscience Center, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark., Taaning R, Nielsen NC, Skrydstrup T
Jazyk: angličtina
Zdroj: The Journal of organic chemistry [J Org Chem] 2012 Jun 15; Vol. 77 (12), pp. 5357-63. Date of Electronic Publication: 2012 May 25.
DOI: 10.1021/jo300746x
Abstrakt: 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.
Databáze: MEDLINE