title: Synthesis and photochromic properties of configurationally varied azobenzene glycosides.
abstract: Spatial orientation of carbohydrates is a meaningful parameter in carbohydrate recognition processes. To vary orientation of sugars with temporal and spatial resolution, photosensitive glycoconjugates with favorable photochromic properties appear to be opportune. Here, a series of azobenzene glycosides were synthesized, employing glycoside synthesis and Mills reaction, to allow "switching" of carbohydrate orientation by reversible E/Z isomerization of the azobenzene N=N double bond. Their photochromic properties were tested and effects of azobenzene substitution as well as the effect of anomeric configuration and the orientation of the sugars 2-hydroxy group were evaluated.
authors: Otto Diels Institute of Organic Chemistry Christiana Albertina University of Kiel Otto-Hahn-Platz 3/4, 24118 Kiel (Germany) E-mail: tklind@oc.uni-kiel.de.
authors: Vijayanand
authors: V
authors: Chandrasekaran
authors: Otto Diels Institute of Organic Chemistry Christiana Albertina University of Kiel Otto-Hahn-Platz 3/4, 24118 Kiel (Germany) E-mail: tklind@oc.uni-kiel.de.
authors: Eugen
authors: E
authors: Johannes
authors: Otto Diels Institute of Organic Chemistry Christiana Albertina University of Kiel Otto-Hahn-Platz 3/4, 24118 Kiel (Germany) E-mail: tklind@oc.uni-kiel.de.
authors: Hauke
authors: H
authors: Kobarg
authors: Otto Diels Institute of Organic Chemistry Christiana Albertina University of Kiel Otto-Hahn-Platz 3/4, 24118 Kiel (Germany) E-mail: tklind@oc.uni-kiel.de.
authors: Frank D
authors: FD
authors: Sönnichsen
authors: Otto Diels Institute of Organic Chemistry Christiana Albertina University of Kiel Otto-Hahn-Platz 3/4, 24118 Kiel (Germany) E-mail: tklind@oc.uni-kiel.de.
authors: Thisbe K
authors: TK
authors: Lindhorst
keywords: Mills reaction; azobenzene glycosides; carbohydrate orientation; glycosylation; photoswitching