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Synthesis of Bifunctional Azobenzene Glycoconjugates for Cysteine‐Based Photosensitive Cross‐Linking with Bioactive Peptides
Author(s) -
Müller Anne,
Kobarg Hauke,
Chandrasekaran Vijayanand,
Gronow Joana,
Sönnichsen Frank D.,
Lindhorst Thisbe K.
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201501571
Subject(s) - azobenzene , bifunctional , chemistry , peptide , glycoconjugate , native chemical ligation , linker , isomerization , cysteine , combinatorial chemistry , side chain , chemical ligation , conjugated system , peptide bond , molecule , organic chemistry , polymer , biochemistry , operating system , computer science , enzyme , catalysis
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 NN 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.