Preparation of some new neoglycoproteins by amidination of bovine serum albumin using 2-imino-2-methoxyethyl 1-thioglycosides

摘要: The cyanomethyl 1-thioglycosides of beta-D-galactose, 6-O-methyl-beta-D-galactose, alpha-L-arabinose, beta-D-fucose, beta-L-fucose, beta-D-glucose, beta-D-xylose, beta-D-allose, alpha-D-mannose, 2-acetamido-2-deoxy-beta-D-glucose, 2-acetamido-2-deoxy-beta-D-galactose, 2-deoxy-beta-D-glucose, and 3-O-methyl-beta-D-glucose were prepared from the respective pseudothiourea derivatives chloroacetonitrile. nitrile function in aglycon was converted to a methyl imido ester by treatment with sodium methoxide methanolic solutions, thereby affording 2-imino-2-methoxyethyl [Lee, Y.C., Stowell, C.P., & Krantz, M.J. (1976) Biochemistry 15, 3956-3963]. stability these reagents investigated. then used attach carbohydrates bovine serum albumin. Amidination could be accomplished within few hours pH range 7-10. extent amidination controlled varying ratio protein amino group. These new neoglycoproteins determine stereospecificity rabbit hepatic carbohydrate-binding system [Stowell, Lee, R.T., Y.C. (1980) (following paper this issue)].