Synthetic assembly of mannose moieties using polymer chemistry and the biological evaluation of its interaction towards concanavalin a

Deepti Diwan, Kohei Shinkai, Toshihiro Tetsuka, Bin Cao, Hidenao Arai, Tetsuo Koyama, Ken Hatano, Koji Matsuoka

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

Protein-carbohydrate interactions exhibit myriad intracellular recognition events, so understanding and investigating their specific interaction with high selectivity and strength are of crucial importance. In order to examine the effect of multivalent binding on the specificity of protein-carbohydrate interactions, we synthesized mannose glycosides as a novel type of glycosylated monomer and glycopolymers of polyacrylamide derivatives with α-mannose (α-Man) by radical polymerization and monitored their strength of interaction with concanavalin A (Con A) by surface plasmon resonance (SPR) detection. In a quantitative test using the Con A-immobilized sensor surface, the kinetic affinity for the synthesized polymers, 8a (KD = 3.3 × 10-6 M) and 8b (KD = 5.3 × 10-5 M), were concentration-dependent, showing strong, specific molecular recognition abilities with lectin. Our study showed the enhancement in recognition specificity for multivalent saccharides, which is often mediated by cell surface carbohydrate-binding proteins that exhibit weak affinity and broad specificity for the individual ligands.

Original languageEnglish
Article number157
JournalMolecules
Volume22
Issue number1
DOIs
StatePublished - Jan 2017

Keywords

  • Concanavalin A
  • Glycopolymers
  • Kinetic affinity
  • Mannose
  • Radical polymerization
  • Surface plasmon resonance

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