Facile synthesis of cyclopeptide-centered multivalent glycoclusters with 'click chemistry' and molecular recognition study by surface plasmon resonance.
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.
Chen
Yong-Xiang
YX
Key Laboratory of Bioorganic Phosphorous Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing, PR China.
Zhao
Lei
L
Huang
Zhi-Ping
ZP
Zhao
Yu-Fen
YF
Li
Yan-Mei
YM
D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D002384:Catalysis; D003208:Concanavalin A / Q000737:chemistry*; D003300:Copper / Q000737:chemistry; D006001:Glycoconjugates / Q000737:chemistry*; D010456:Peptides, Cyclic / Q000138:chemical synthesis / Q000737:chemistry*; D011485:Protein Binding; D020349:Surface Plasmon Resonance
D000480:Alkynes; D001386:Azides; D006001:Glycoconjugates; D010456:Peptides, Cyclic; D003208:Concanavalin A; D003300:Copper