Quantitative fluorine NMR to determine carbohydrate density on glyconanomaterials synthesized from perfluorophenyl azide-functionalized silica nanoparticles by click reaction.
A quantitative fluorine NMR ((19)F qNMR) method was developed to determine the carbohydrate density on glyconanomaterials. Mannose (Man)- and galactose (Gal)-conjugated silica nanoparticles (SNPs) were synthesized from perfluorophenyl azide (PFPA)-functionalized SNPs and propargylated Man or Gal by copper-catalyzed azide-alkyne cycloaddition (click reaction). After treating PFPA-SNPs or Man-SNPs with hydrofluoric acid followed by lyophilization, the remaining residues were directly subjected to (19)F NMR analysis. The density of PFPA on PFPA-SNP was determined to be 7.7 ± 0.2 × 10(-16) nmol/nm(2) and Man on Man-SNP to be 6.4 ± 0.2 × 10(-16) nmol/nm(2) giving a yield of ∼83% for the click coupling reaction. The apparent dissociation constant (Kd) of Man-SNPs with fluorescein isothiocyanate (FITC)-concanavalin A (Con A) was determined using a fluorescence competition assay to be 0.289 ± 0.003 μM, which represents more than 3 orders of magnitude affinity increase compared to free Man with Con A.
Department of Chemistry, KTH - Royal Institute of Technology , Teknikringen 30, S-10044 Stockholm, Sweden.
Na
N
Kong
Department of Chemistry, KTH - Royal Institute of Technology , Teknikringen 30, S-10044 Stockholm, Sweden.
Juan
J
Zhou
Department of Chemistry, University of Massachusetts Lowell , 1 University Ave., Lowell, Massachusetts 01854, United States.
JaeHyeung
J
Park
Department of Chemistry, KTH - Royal Institute of Technology , Teknikringen 30, S-10044 Stockholm, Sweden.
Sheng
S
Xie
Department of Chemistry, KTH - Royal Institute of Technology , Teknikringen 30, S-10044 Stockholm, Sweden.
Olof
O
Ramström
Department of Chemistry, KTH - Royal Institute of Technology , Teknikringen 30, S-10044 Stockholm, Sweden.|Department of Chemistry, University of Massachusetts Lowell , 1 University Ave., Lowell, Massachusetts 01854, United States.
Mingdi
M
Yan
D001386:Azides / Q000737:chemistry*; D057930:Click Chemistry; D003208:Concanavalin A / Q000737:chemistry; D005461:Fluorine / Q000737:chemistry; D005690:Galactose / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D008358:Mannose / Q000737:chemistry*; D053758:Nanoparticles / Q000737:chemistry*; D012822:Silicon Dioxide / Q000737:chemistry*
D001386:Azides; D006845:Hydrocarbons, Fluorinated; D008024:Ligands; C556136:perfluorophenyl azide; D003208:Concanavalin A; D005461:Fluorine; D012822:Silicon Dioxide; D008358:Mannose; D005690:Galactose