Synthesis of a tri- and tetradeoxy analogue of methyl 3,6-di-O-alpha-D-mannopyranosyl-alpha-D-mannopyranoside for investigation of the binding site of various plant lectins.
The synthesis of a the 2,4,3'-trideoxy and 2,4,3',4'-tetradeoxy analogues of the trimannoside part of the core structure of N-linked glycoproteins, methyl 3,6-di-O-alpha-D-mannopyranosyl-alpha-D-mannopyranoside, is described. A 2,4-dideoxy (1-->6) linked disaccharide was used as a common intermediate acceptor, which was coupled with a 3-deoxy and a 3,4-dideoxy benzochlorosugar donor, the latter prepared from methyl alpha-D-mannopyranoside in five steps. Despite the acid-sensitive donors and acceptor, acceptable glycosylation yields were obtained of both the trideoxy- and the tetradeoxy trisaccharide using silver triflate as a promoter (65 and 51%, respectively). Deprotection in one step then gave the target products.
Oscarson
S
S
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden.
Svahnberg
P
P
D001665:Binding Sites; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D006031:Glycosylation; D037102:Lectins / Q000737:chemistry*; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000737:chemistry*
D037102:Lectins; D009844:Oligosaccharides; C093348:methyl 3,6-di-O-(mannopyranosyl)mannopyranoside