Facile synthesis of cyclopeptide-centered multivalent glycoclusters with 'click chemistry' and molecular recognition
Yong-Xiang Chen1, Lei Zhao, Zhi-Ping Huang
1Key Laboratory of Bioorganic Phosphorous Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing, PR China.
Abstract:
A facile synthesis of cyclopeptide-centered multivalent glycoclusters using Cu(I) catalyzed Huisgen 1,3-dipolar cycloaddition of azides and terminal alkynes, so called 'click chemistry', has been developed. The affinities of mannose-specific protein Concanavalin A (Con A) toward two synthetic glycoclusters respectively bearing divalent or tetravalent mannoses were investigated by surface plasmon resonance (SPR). It is founded that the tetravalent glycocluster has 3.0-fold increase in binding affinity relative to the divalent glycoluster (valency-corrected values), which indicates the potential of this system in investigating carbohydrate-protein interactions.
