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Synthesis of Bifunctional Azobenzene Glycoconjugates for Cysteine‐Based Photosensitive Cross‐Linking with Bioactive Peptides
Authors:Anne Müller  Hauke Kobarg  Dr Vijayanand Chandrasekaran  Joana Gronow  Prof Frank D Sönnichsen  Prof Thisbe K Lindhorst
Institution:Otto Diels Institute of Organic Chemistry, Christiana Albertina University of Kiel, Otto‐Hahn‐Platz 3/4, 24118 Kiel (Germany), Fax: (+49)?431‐8807410
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.
Keywords:azobenzene glycoconjugates  cysteine ligation  molecular switches  peptide cross‐linking  photocontrol
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