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Multivalent 1,2,3‐Triazole‐Linked Carbohydrate Mimetics by Huisgen–Meldal‐Sharpless Cycloadditions of an Azidopyran
Author(s) -
Salta Joana,
Arp Fabian F.,
Kühne Christian,
Reissig HansUlrich
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001389
Subject(s) - chemistry , cycloaddition , triazole , click chemistry , enantiopure drug , combinatorial chemistry , triethylamine , azide , pyran , carbohydrate , stereochemistry , ligand (biochemistry) , catalysis , organic chemistry , enantioselective synthesis , biochemistry , receptor
Starting from an enantiopure 3‐azido‐substituted pyran derivative and various oligo‐alkynes a series of multivalent 1,2,3‐triazole‐linked carbohydrate mimetics was synthesized. The copper‐catalyzed Huisgen–Meldal‐Sharpless cycloaddition (CuAAC) served as key coupling reaction. Cu/C in the presence of triethylamine proved to be a good catalytic system in most cases. Tri‐, tetra‐, hexa‐, and octavalent compounds with typical rigid or flexible core units were prepared. The most complex compound contains a C 60 ‐fullerene center leading to a dodecavalent carbohydrate mimetic. Only a few of the multivalent target compounds could be converted into pure O ‐sulfated derivatives that are required for their evaluation as L‐ and P‐selectin ligands. Nevertheless, preliminary experiments suggest that the dodecavalent C 60 ‐derived compound may be a promising ligand of these biologically important proteins with IC 50 values in the low nanomolar range.