Carbohydrate-based Cu(I) stabilizing ligands and their use in the synthesis of carbohydrate-ferrocene conjugates

Magnus S Schmidt; Kim Leitner; Moritz Welter; Lena A Wurmthaler; Markus Ringwald

doi:10.1016/j.carres.2014.01.005

Carbohydrate-based Cu(I) stabilizing ligands and their use in the synthesis of carbohydrate-ferrocene conjugates

Carbohydr Res. 2014 Mar 31:387:42-5. doi: 10.1016/j.carres.2014.01.005. Epub 2014 Jan 21.

Authors

Magnus S Schmidt¹, Kim Leitner², Moritz Welter³, Lena A Wurmthaler⁴, Markus Ringwald⁵

Affiliations

¹ MCAT GmbH, Hermann-von-Vicari-Str. 23, 78464 Konstanz, Germany. Electronic address: schmidt@mcat.de.
² Department of Chemistry, University of Konstanz, Germany. Electronic address: kim.leitner@uni-konstanz.de.
³ Department of Chemistry, University of Konstanz, Germany. Electronic address: moritz.welter@uni-konstanz.de.
⁴ Department of Chemistry, University of Konstanz, Germany. Electronic address: lena.wurmthaler@uni-konstanz.de.
⁵ MCAT GmbH, Hermann-von-Vicari-Str. 23, 78464 Konstanz, Germany. Electronic address: ringwald@mcat.de.

PMID: 24583527
DOI: 10.1016/j.carres.2014.01.005

Abstract

A series of carbohydrate-ferrocene conjugates have been synthesized by copper(I)-catalyzed cycloaddition of carbohydrate-azides and ethynylferrocene (CuAAC). Newly carbohydrate-based tris-triazoles have been used as Cu(I) stabilizing ligands and showed at least comparable, in some cases even better results compared to the use of tris-(benzyltriazolylmethyl)amine (TBTA).

Keywords: Carbohydrates; Click chemistry; Cu(I) stabilizing ligands; Ferrocene; Glycoconjugates.

MeSH terms

Alkynes / chemistry
Azides
Carbohydrates / chemistry*
Catalysis
Click Chemistry
Copper / chemistry*
Ferrous Compounds / chemistry*
Ligands
Metallocenes
Molecular Structure
Triazoles / chemistry

Substances

Alkynes
Azides
Carbohydrates
Ferrous Compounds
Ligands
Metallocenes
Triazoles
Copper
ferrocene