title: Synthesis of Bifunctional Azobenzene Glycoconjugates for Cysteine-Based Photosensitive Cross-Linking with Bioactive Peptides.
abstract: Azobenzene linker molecules can be utilized to control peptide/protein function when they are ligated to appropriately spaced amino acid side chains of the peptide. This is because the photochemical E/Z isomerization of the azobenzene N=N double bond allows to switch peptide conformation between folded and unfolded. In this context, we have introduced carbohydrate-functionalized azobenzene derivatives in order to advance the biocompatible properties of azobenzene peptide linkers. Chloroacetamide-functionalized and O-allylated carbohydrate derivatives were synthesized and conjugated with azobenzene to achieve new bifunctional cross-linkers, in order to allow ligation to cysteine side chains by nucleophilic substitution or thiol-ene reaction, respectively. The photochromic properties of the new linker glycoconjugates were determined and first ligation reactions performed.
authors.affiliation: Otto Diels Institute of Organic Chemistry, Christiana Albertina University of Kiel, Otto-Hahn-Platz 3/4, 24118 Kiel (Germany), Fax: (+49) 431-8807410.
authors.forename: Anne
authors.initials: A
authors.lastname: Müller
authors.affiliation: Otto Diels Institute of Organic Chemistry, Christiana Albertina University of Kiel, Otto-Hahn-Platz 3/4, 24118 Kiel (Germany), Fax: (+49) 431-8807410.
authors.forename: Hauke
authors.initials: H
authors.lastname: Kobarg
authors.affiliation: Otto Diels Institute of Organic Chemistry, Christiana Albertina University of Kiel, Otto-Hahn-Platz 3/4, 24118 Kiel (Germany), Fax: (+49) 431-8807410.
authors.forename: Vijayanand
authors.initials: V
authors.lastname: Chandrasekaran
authors.affiliation: Otto Diels Institute of Organic Chemistry, Christiana Albertina University of Kiel, Otto-Hahn-Platz 3/4, 24118 Kiel (Germany), Fax: (+49) 431-8807410.
authors.forename: Joana
authors.initials: J
authors.lastname: Gronow
authors.affiliation: Otto Diels Institute of Organic Chemistry, Christiana Albertina University of Kiel, Otto-Hahn-Platz 3/4, 24118 Kiel (Germany), Fax: (+49) 431-8807410.
authors.forename: Frank D
authors.initials: FD
authors.lastname: Sönnichsen
authors.affiliation: Otto Diels Institute of Organic Chemistry, Christiana Albertina University of Kiel, Otto-Hahn-Platz 3/4, 24118 Kiel (Germany), Fax: (+49) 431-8807410. tklind@oc.uni-kiel.de.
authors.forename: Thisbe K
authors.initials: TK
authors.lastname: Lindhorst
mesh_terms: D001391:Azo Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D003432:Cross-Linking Reagents / Q000737:chemistry*; D003545:Cysteine / Q000737:chemistry*; D006001:Glycoconjugates / Q000737:chemistry*; D007536:Isomerism; D008958:Models, Molecular; D010455:Peptides / Q000737:chemistry*; D010777:Photochemistry
chemical_list: D001391:Azo Compounds; D003432:Cross-Linking Reagents; D006001:Glycoconjugates; D010455:Peptides; C009850:azobenzene; D003545:Cysteine
keywords: azobenzene glycoconjugates; cysteine ligation; molecular switches; peptide cross-linking; photocontrol