93496-44-7

Usage

InChI:InChI=1/C21H31NO11/c1-10(24)22-14-17(27)16(26)13(33-20(14)30-8-11-5-3-2-4-6-11)9-31-21-19(29)18(28)15(25)12(7-23)32-21/h2-6,12-21,23,25-29H,7-9H2,1H3,(H,22,24)/t12?,13?,14-,15-,16-,17+,18-,19-,20-,21+/m0/s1

Upstream product

• 3554-93-6 benzyl 2-acetamido-2-deoxy-α-D-galactopyranoside 
• 3150-24-1 4-nitrophenyl-β-D-galactopyranoside 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 3554-95-8 benzyl 2-acetamido-3-O-acetyl-2-deoxy-α-D-galactopyranoside 
• 93496-43-6 Acetic acid (2R,3R,4S,5S,6R)-3,5-diacetoxy-2-((2R,3R,4R,5R,6S)-4-acetoxy-5-acetylamino-6-benzyloxy-3-hydroxy-tetrahydro-pyran-2-ylmethoxy)-6-acetoxymethyl-tetrahydro-pyran-4-yl ester 

Downstream Products

• 93601-73-1 2-acetamido-2-deoxy-6-O-β-D-galactopyranosyl-β-D-galactopyranose 
• 93601-72-0 2-acetamido-2-deoxy-6-O-β-D-galactopyranosyl-α-D-galactopyranose 

Relevant academic research and scientific papers

Facile one-step syntheses of modified O-glycoprotein Galβ1-3GalNAc structures by transglycosylation employing three β-galactosidases from bovine testes, Xanthomonas manihotis, and Bacillus circulans

Natural O-glycoproteins such as the Thomsen-Friedenreich antigen or gangliosides contain the motif Galβ1-3GalNAc as an important disaccharide with significant biologic activity. The arrangement of spatial functionalities in this structure are of particular interest with regard to the development of potential leads en route to pharmaceuticals. Therefore, it was desired to obtain access to a range of modified derivatives of the aforementioned motif paying particular attention to introducing specific deoxy functions instead of hydroxyl groups. Copyright Taylor & Francis, Inc.

Characterization of the Immobilized β-Galactosidase C from Bacillus circulans and the Production of β(1→3)-linked Disaccharides

A recombinant β-galactosidase, which was obtained from the β-galactosidase C gene of Bacillus circulans and cleaves the non-reducing end galactosyl residue of β(1→3)-linkages selectively, was immobilized using CNBr-Sepharose. Although the effect of pH was not changed by the immobilization, the thermostability and stability in the presence of DMF were increased. Optimization of the transglycosylation using para-nitrophenyl β-D-galactopyranoside as a donor and benzyl-α-D-N-acetylgalactosaminide as an acceptor afforded a β(1→3)-linked disaccharide derivative with 62% molar yield in a gram scale synthesis. Using the methyl-analogue as an acceptor, 53% of the acceptor was converted to the respective β(1→3)-disaccharide.

Synthesis of 2-acetamido-2-deoxy-6-O-beta-D-galactopyranosyl-D-galactopyranose and o-nitrophenyl 2-acetamido-2-deoxy-6-O-beta-D-galactopyranosyl -alpha-D-galactopyranoside.

Acetalation of o-nitrophenyl 2-acetamido-2-deoxy-alpha-D-galactopyranoside with p-methoxybenzaldehyde-zinc chloride complex afforded the 4,6-O-(p-methoxybenzylidene) derivative (1). Acetylation of 1 with pyridine-acetic anhydride gave the crystalline mono