288574-18-5Relevant academic research and scientific papers
The C-disaccharide α-C(1→3)-mannopyranoside of N-acetylgalactosamine is an inhibitor of glycohydrolases and of human α-1,3-fucosyltransferase VI. Its epimer α-(1→3)-mannopyranoside of N-acetyltalosamine is not
Pasquarello, Carla,Picasso, Sylviane,Demange, Raynald,Malissard, Martine,Berger, Eric G.,Vogel, Pierre
, p. 4251 - 4260 (2000)
The radical C-glycosidation of (-)-(1S,4R,5R,6R)-6-endo-chloro-3- methylidene-5-exo-(phenylseleno)-7-oxabicyclo[2.2.1]heptan-2-one ((-)-4) with 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl bromide gave (+)-(1S,3R,4R,5R,6R)- 6-endo-chloro-5-exo-(phenylseleno)-3-endo-(1',3',4',5',-tetra-O-acetyl-2',6'- anhydro-7'-deoxy-D-glycero-D-manno-heptitol-7'-C-yl)-7-oxabicyclo[2.2.1]hept- 2-one ((+)-5) that was converted into (+)-(1R,2S,5R,6R)-5-acetamido-3-chloro- 2-hydroxy-6-(1',3',4',5'-tetra-O-acetyl)-2',6'-anhydro-7'-deoxy-D-glycero-D- manno-heptitol-7'-C-yl)cyclohex-3-en-1-yl acetate ((+)-10) and into (+)- (1R,2S,5R,6S)-5-bromo-3-chloro-2-hydroxy-6-(1,3,4,5 -tetra-O-acetyl- 2',6',anhydro-7'-deoxy-D-glycero-D-manno-heptitol-7'-C-yl)cyclohex-3-en-1-yl acetate ((+)-19). Ozonolysis of (+)-10 and further transformations provided 2-acetamido-2,3-dideoxy-3-C-(2',6'-anhydro-7'-deoxy-D-glycero-D-manno- heptitol-7'-C-yl)-D-galactose (α-C(1→3)-D-mannopyranoside of N- acetylgalactosamine (α-D-Manp- (1→3)CH2-D-GalNAc): 1). Displacement of the bromide (+)-19 with NaN3 in DMF provided the corresponding azide ((-)-20) following a S(N)2 mechanism. Ozonolysis of (-)-20 and further transformations led to 2-acetamido-2,3-dideoxy-3-C-(2',6'-anhydro-7'-deoxy-D-glycero-D-manno- heptitol-7'-C-yl)-D-talose (α-C(1→3)-D-mannopyranoside of N-acetyl D- talosamine (α-D-Manp-(1→3)CH2-D-TalNAc): 2). The neutral C-disaccharide 1 inhibits several glycosidases (e.g., β-galactosidase from jack bean with K(i) = 7.5 μM, α-L-fucosidase from human placenta with K(i) = 28 μM, β- glucosidase from Caldocellum saccharolyticum with K(i) = 18 μM) and human α-1,3-fucosyltransferase VI (Fuc-TVI) with K(i) = 120 μM whereas it 2- epimer 2 does not. Double reciprocal analysis showed that the inhibition of Fuc-TVI by 1 displays a mixed pattern with respect to both the donor sugar GDP-fucose-and the acceptor LacNAc with K(i) of 123 and 128 μM, respectively.
