Premium
Efficient Synthesis of Muramic and Glucuronic Acid Glycodendrimers as Dengue Virus Antagonists
Author(s) -
GarcíaOliva Cecilia,
Cabanillas Alfredo H.,
Perona Almudena,
Hoyos Pilar,
Rumbero Ángel,
Hernáiz María J.
Publication year - 2020
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.201903788
Subject(s) - chemistry , muramic acid , surface plasmon resonance , dengue virus , glycoconjugate , glucuronic acid , combinatorial chemistry , stereochemistry , dengue fever , biochemistry , nanotechnology , polysaccharide , virology , nanoparticle , materials science , biology , peptidoglycan , enzyme
Abstract Carbohydrates are involved in many important pathological processes, such as bacterial and viral infections, by means of carbohydrate‐protein interactions. Glycoconjugates with multiple carbohydrates are involved in multivalent interactions, thus increasing their binding strengths to proteins. In this work, we report the efficient synthesis of novel muramic and glucuronic acid glycodendrimers as potential Dengue virus antagonists. Aromatic scaffolds functionalized with a terminal ethynyl groups were coupled to muramic and glucuronic acid azides by click chemistry through optimized synthetic strategies to afford the desired glycodendrimers with high yields. Surface Plasmon Resonance studies have demonstrated that the compounds reported bind efficiently to the Dengue virus envelope protein. Molecular modelling studies were carried out to simulate and explain the binding observed. These studies confirm that efficient chemical synthesis of glycodendrimers can be brought about easily offering a versatile strategy to find new active compounds against Dengue virus.