CHIMIE DES SUCRES SANS GROUPEMENTS PROTECTEURS-I-ESTERIFICATION REGIOSELECTIVE DE L'HYDROXYLE ANOMERE DU LACTOSE, DU MALTOSE ET DU GLUCOSE

Article abstract of DOI:10.1016/0040-4020(86)80009-6

Treatment of acyl chlorides 4 with mercaptothiazoline, mercaptobenzothiazole, p-nitrophenol and 8-hydroxyquinoline in the presence of Et3N, afforded high yields of the corresponding reactive amides 5a-h,S-thioesters 6e-h and aryl esters 7e-h and 8a-h, respectively.The esters 6e-h, 7e-h and 8e-h reacted with excess β-lactose in pyridine, to give the corresponding β-esters 9e-h resulting from esterification of the anomeric hydroxyl of the sugar.The amides 5c, f-h gave the α-lactosyl esters 9c, f-h.The amide 5e and the esters 8b, c, e reacted with β-maltose, thus affording the corresponding β-maltosyl esters 10b, c, e, whereas the compounds 8a-e reacted with β-glucose, yielding the corresponding β-glucosyl esters 11a-e.This appears to be one of the very few selective chemical modifications of sugars known, which do not involve the toilsome protection-deprotection methology.The now commercially available maltosyl and glucosyl esters 10e and 11d-e are new non-ionic, and water soluble detergents which could be used for studies of cell membrane proteins.