138479-76-2Relevant academic research and scientific papers
4-O-β-D-Galactopyranosyl-D-xylose: A new synthesis and application to the evaluation of intestinal lactase
Rivera-Sagredo,Fernandez-Mayoralas,Jimenez-Barbero,Martin-Lomas,Villanueva,Aragon
, p. 129 - 135 (1992)
4-O-β-D-Galactopyranosyl-D-xylose (2) was prepared from benzyl 2,3-O-isopropylidene-β-D-xylopyranoside by glycosylation with 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl bromide and subsequent deprotection. Compound 2 was hydrolyzed in vitro by intestinal lactase; the V(max) was 25% of that with lactose and the K(m) was 370 mM (cf. 27 mM for lactose). Oral administration of 2 to suckling rats led to urinary excretion of D-xylose which could be estimated colorimetrically. 4-O-β-D-Galactopyranosyl-D-xylose (2) was prepared from benzyl 2,3-O-isopropylidene-β-D-xylopyranoside by glycosylation with 2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl bromide and subsequent deprotection. Compound 2 was hydrolyzed in vitro by intestinal lactase; the Vmax was 25% of that with lactose and the Ktu was 370mM (cf. 27mM for lactose). Oral administration of 2 to suckling rats led to urinary excretion of D-xylose which could be estimated colorimetrically.
The synthesis of a carbohydrate-like dihydrooxazine and tetrahydrooxazine as putative inhibitors of glycoside hydrolases: A direct synthesis of isofagomine
Best, Wayne M.,Macdonald, James M.,Skelton, Brian W.,Stick, Robert V.,Matthew,Tilbrook,White, Allan H.
, p. 857 - 865 (2007/10/03)
The treatment of benzyl 2,3-O-isopropylidene-β-L-xylopyranoside with N-hydroxyphthalimide under Mitsunobu conditions, followed by protecting-group interchange, gave benzyl 4-O-[(tert-butoxycarbonyl)amino]-2,3-O-isopropylidene-α-D-arabinoside. Mild acid hydrolysis and catalytic hydrogenolysis afforded 4-O-[(tert-butoxycarbonyl)amino]-D-arabinose that, upon heating in water, gave the dihydrooxazine [(4R,5S,6R)-5,6-dihydro-4,5-dihydroxy-6-hydroxymethyl-4H-1,2-oxazine] as a crystalline solid. A single-crystal structure determination of this solid showed it to exist in the 5H6 conformation. Reduction of the dihydrooxazine gave the tetrahydrooxazine [(4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-3,4,5,6-tetrahydro-2H-1,2-oxazine]. The dihydrooxazine was an effective inhibitor of two β-glucosidases (Ki = 27 and 35 μM). Benzyl 2,3-O-isopropylidene-β-L-xylopyranoside, via the derived imidazylate, was converted into a nitrile that, upon reduction and protecting-group manipulations, gave benzyl 4-C-aminomethyl-4-deoxy-α-D-arabinoside. Treatment of this amine with hydrogen and palladium-on-carbon gave isofagomine.
Synthesis of glycopeptides from the carbohydrate-protein linkage region of proteoglycans
Rio, Sandrine,Beau, Jean-Marie,Jacquinet, Jean-Claude
, p. 71 - 90 (2007/10/02)
2,3,4,6-Tetra-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate was condensed with benzyl 2,3-O-isopropylidene-β-D-xylopyranoside to give the corresponding β-(1->4)-linked disaccharide derivative, which was transformed into 2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-α-D-xylopyranosyl trichloroacetimidate.This glycosyl donor was condensed with a set of selectively C,N-protected L-seryl-glycine dipeptide units.Selective deblocking at the C- or N-termini of the glycosylated or non-glycosylated dipeptide segments, and coupling using the mixed-anhydride procedure allowed the construction in high yield of partially or fully glycosylated oligopeptides from the carbohydrate-protein linkage region of proteoglycans.
