Interactions of aromatic mannosyl disulfide derivatives with concanavalin A: synthesis, thermodynamic and NMR spectroscopy studies.
alpha-D-Mannopyranosyl units were attached to an aromatic scaffold through disulfide linkages to obtain mono- to trivalent glycosylated ligands for lectin binding studies. Isothermal titration calorimetric (ITC) measurements indicated that binding affinities of these derivatives to Concanavalin A (Con A) were comparable to or slightly higher than that of methyl alpha-D-mannopyranoside (K(a) values in the range of 10(4)M(-1)). The stoichiometries of the lectin-ligand complexes were in agreement with the formal valencies (1-3) of the respective ligands indicating cross-linking in interactions with the di- and trivalent derivatives. Multivalency effects could not, however, be observed with the latter. These ligands were shown to bind to the carbohydrate binding site of Con A using saturation transfer difference (STD) NMR competition experiments.
Murthy
Bandaru Narasimha
BN
Department of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, India.
Sinha
Sharmistha
S
Surolia
Avadhesha
A
Jayaraman
Narayanaswamy
N
Szilágyi
László
L
Szabó
Ildikó
I
Kövér
Katalin E
KE
D001554:Benzene / Q000737:chemistry; D002151:Calorimetry; D003208:Concanavalin A / Q000737:chemistry* / Q000378:metabolism; D004220:Disulfides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D006027:Glycosides / Q000737:chemistry / Q000378:metabolism; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D008358:Mannose / Q000737:chemistry*; D013816:Thermodynamics
D004220:Disulfides; D006027:Glycosides; D008024:Ligands; D003208:Concanavalin A; D001554:Benzene; D008358:Mannose