A method for bioconjugation of carbohydrates using Diels-Alder cycloaddition.
Diels-Alder-type cycloaddition of an electronically matched pair of saccharide-linked conjugated dienes and a dienophile-equipped protein gives neoglycoproteins at ambient temperature in pure water with a reaction half-life of approximately 2 h. Uncoupled saccharides can be recovered by diafiltration with complete conservation of the diene moiety, thus allowing their repeated use. The procedure described is the first for creating a carbon-carbon covalent bond in the bioconjugation step between a saccharide and a protein.
Pozsgay
Vince
V
Laboratory of Developmental and Molecular Immunity, and Laboratory of Cellular and Molecular Biophysics, National Institute of Child Health and Human Development, National Institutes of Health, Bethesda, Maryland 20892-2720, USA. vipo@helix.nih.gov
Vieira
Nancy E
NE
Yergey
Alfred
A
D001665:Binding Sites; D002241:Carbohydrates / Q000737:chemistry*; D003432:Cross-Linking Reagents; D006207:Half-Life; D006801:Humans; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D008301:Maleimides / Q000737:chemistry; D015394:Molecular Structure; D012709:Serum Albumin / Q000737:chemistry*; D014867:Water
D002241:Carbohydrates; D003432:Cross-Linking Reagents; D008301:Maleimides; D012709:Serum Albumin; D014867:Water; C043592:maleimide