Preparation of  new omega-aldehydoalkyl 1-thio-D-glycopyranosides, and their coupling to bovine serum albumin by reductive alkylation.
Synthesis of two omega-aldehydoalkyl 1-thioglycosides of D-glucopyranose and of D-galactopyranose is described. 3-Oxopropyl and 2-oxoethyl 1-thioglycosides were prepared by treating a tetra-O-acetyl-1-thioaldose with either acrolein or 2-bromo-acetaldehyde, followed by O-deacetylation under mild conditions. These omega-aldehydoalkyl 1-thioglycosides were successfully attached to bovine serum albumin (BSA) by reductive alkylation as described previously. With the 3-oxopropyl 1-thioglycosides, much higher levels of sugar attachment (e.g., approximately 80 mol of sugar per mol of BSA) were attained than hitherto possible with any sugar derivative tested.
D000478:Alkylation; D000818:Animals; D002417:Cattle; D007202:Indicators and Reagents; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D011485:Protein Binding; D012710:Serum Albumin, Bovine; D013865:Thioglycosides / Q000138:chemical synthesis*
D007202:Indicators and Reagents; D013865:Thioglycosides; D012710:Serum Albumin, Bovine