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Search for "azobenzene glycosides" in Full Text gives 2 result(s) in Beilstein Journal of Organic Chemistry.

Orthogonal photoswitching of heterobivalent azobenzene glycoclusters: the effect of glycoligand orientation in bacterial adhesion

  • Leon M. Friedrich and
  • Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2025, 21, 736–748, doi:10.3762/bjoc.21.57

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  • ]. Specifically, the reversible E/Z isomerization of the azo group in azobenzene glycosides is suited to control the spatial presentation of glycoligands and, for example, switch carbohydrate-specific bacterial adhesion on and off [20][21][22][23]. Indeed, glycoazobenzene derivatives are excellent tools to
  • following conclusions can be drawn. (i) In all inspected azobenzene glycoconjugates (1, 2, 4, and 5), a terminal α-ᴅ-mannopyranoside unit is complexed within the FimH CRD, as expected. (ii) The isomeric state of the azo group in the monovalent azobenzene glycosides 4 and 5 alters the orientation of the non
  • bivalent azobenzene glycosides 1 and 2 in the various isomeric states (EE, EZ, ZE, and ZZ) and the lectin FimH reach a complexity which obscures the effect of azo group isomerization. (iv) Calculated binding energies for the highest affinity isomers of 1 and 2, respectively, (−107.61 and −96.22 kcal mol−1
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Published 08 Apr 2025

Synthesis and testing of the first azobenzene mannobioside as photoswitchable ligand for the bacterial lectin FimH

  • Vijayanand Chandrasekaran,
  • Katharina Kolbe,
  • Femke Beiroth and
  • Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2013, 9, 223–233, doi:10.3762/bjoc.9.26

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  • adhesive surfaces. Keywords: azobenzene glycosides; bacterial adhesion; E/Z photoisomerisation; FimH antagonists; mannobiosides; molecular switches; sweet switches; Introduction Adhesion of bacteria to surfaces can be a severe problem both in vivo and in vitro. Hence, inhibition of bacterial adhesion by
  • ) in order to make a photoswitchable FimH antagonist available. Photoirradiation of azobenzene glycosides at ~365 nm effects E→Z isomerisation of the N=N double bond, and thermal relaxation or irradiation at ~450 nm leads to Z→E back isomerisation [13][14]. In the case that the E→Z isomerisation
  • , glycosylation of the key intermediate 10 by using the mannosyl donor 3 gave the desired mannobioside 11 in 76% yield. Finally, removal of the O-acetyl groups according to Zemplén led to the unprotected 1,3-linked target mannobioside α-D-Man-(1→3)-D-Man (2). With the two azobenzene glycosides 6 and 2 at hand
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Published 01 Feb 2013
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