Synthesis of omega-(methoxycarbonyl)alkyl and 9-(methoxycarbonyl)-3,6-dioxanonyl glycopyranosides for the preparation of carbohydrate-protein conjugates.
omega-(Methoxycarbonyl)alkyl glycopyranosides of D-mannose having C4, C7, C9, C12, and C15 carbon chains, L-fucose and 2-acetamido-2-deoxy-D-mannose having C7 and C9 carbon chains, D-xylose and 2-acetamido-2-deoxy-L-fucose having a C9 carbon chain, and 9-(methoxycarbonyl)-3,6-dioxanonyl glycopyranosides of D-mannose, 2-acetamido-2-deoxy-D-mannose, and L-fucose were synthesized as intermediates for coupling to human serum albumin in order to examine the effect of chain length and hydrophobicity of the spacer arm on the binding specificity of lectins. 8-(Methoxycarbonyl)octyl glycosides of beta-D-Man-(1----2)-alpha-D-Man, alpha-D-Man-(1----2)-alpha-D-Man, alpha-D-ManNAc-(1----2)-alpha-D-Man, beta-D-GlcNAc-(1----2)-alpha-D-Man, and their 6-O-positional isomers, beta-D-Man-(1----6)-alpha-D-Man, alpha-D-Man-(1----6)-alpha-D-Man, alpha-D-ManNAc-(1----6)-alpha-D-Man, and beta-D-GlcNAc-(1----6)-alpha-D-Man, were also synthesized.
Sugawara
T
T
Drug Delivery System Institute, Ltd., Noda Research Laboratories, Science University of Tokyo, Chiba, Japan.
Irie
K
K
Iwasawa
H
H
Yoshikawa
T
T
Okuno
S
S
Watanabe
H K
HK
Kato
T
T
Shibukawa
M
M
Ito
Y
Y
D002240:Carbohydrate Sequence; D002352:Carrier Proteins / Q000138:chemical synthesis*; D004337:Drug Carriers / Q000138:chemical synthesis / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry*; D008969:Molecular Sequence Data; D011956:Receptors, Cell Surface
D002352:Carrier Proteins; D004337:Drug Carriers; D006027:Glycosides; D011956:Receptors, Cell Surface; C055213:saccharide-binding proteins