Activation of polysaccharides with 2-iminothiolane and its uses.
2-Iminothiolane, a cyclic thioimidate, is known to react readily with amino groups of proteins to give amidinated derivatives containing reactive sulfhydryl groups. In this report it will be shown that 2-iminothiolane also reacts with hydroxyl and sulfhydryl groups. Such a reaction with hydroxyl groups can be used to introduce sulfhydryl groups into polysaccharides. When this reaction is carried out in the presence of 4,4'-dithiodipyridine, polysaccharides containing 4-dithiopyridyl groups can be prepared. These activated polysaccharides couple easily via intermolecular disulfide bond formation with proteins containing thiol or 4-dithiopyridyl groups. The resulting polysaccharide--protein conjugates have good stability, and they are useful reagents for different biochemical applications such as the purification of proteins containing thiol groups and affinity chromatography.
D000485:Allergens; D052179:Antigens, Plant; D055598:Chemical Phenomena; D002621:Chemistry; D002846:Chromatography, Affinity; D007096:Imidoesters; D007106:Immune Sera; D007700:Kinetics; D010940:Plant Proteins; D011058:Pollen; D011134:Polysaccharides; D011506:Proteins / Q000302:isolation & purification; D012685:Sepharose / Q000031:analogs & derivatives; D013438:Sulfhydryl Compounds
D000485:Allergens; C026967:Amb a I protein, Ambrosia artemisiifolia; D052179:Antigens, Plant; D007096:Imidoesters; D007106:Immune Sera; D010940:Plant Proteins; D011134:Polysaccharides; D011506:Proteins; D013438:Sulfhydryl Compounds; C005905:methyl 4-mercaptobutyrimidate; D012685:Sepharose