Isotope-Labeling of the Fibril Binding Compound FSB via a Pd-Catalyzed Double Alkoxycarbonylation

We have synthesized two isotopically labeled variants of the β-amyloid binding compound FSB possessing 13C-labels on the two terminal aryl carboxylic acid moieties. One of these was also fully deuterated on the olefinic spacers. The 13C-isotope labeling was achieved applying a Pd-catalyzed methoxyca...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2012-06, Vol.77 (12), p.5357-5363
Main Authors: Burhardt, Mia N, Taaning, Rolf, Nielsen, Niels Chr, Skrydstrup, Troels
Format: Article
Language:English
Subjects:
Alkynes - chemistry
Amyloid - chemistry
Analytical, structural and metabolic biochemistry
Biological and medical sciences
Catalysis
Chemistry
Exact sciences and technology
Fundamental and applied biological sciences. Psychology
Isotope Labeling - methods
Labelled compounds chemistry
Molecular Structure
Organic chemistry
Palladium - chemistry
Protein Binding
Protein Carbonylation
Proteins
Reactivity and mechanisms
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:We have synthesized two isotopically labeled variants of the β-amyloid binding compound FSB possessing 13C-labels on the two terminal aryl carboxylic acid moieties. One of these was also fully deuterated on the olefinic spacers. The 13C-isotope labeling was achieved applying a Pd-catalyzed methoxycarbonylation of the corresponding aryl chlorides with externally (ex situ) generated 13C-labeled CO. Application of the Shirakawa–Hayashi protocol for the Pd-catalyzed reduction of a dialkyne intermediate using D2O allowed for the selective deuterium labeling of the two trans-C,C double bonds of FSB.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo300746x