127501-24-0

Basic information

• Product Name: methyl 2,3,5-tri-O-benzyl-β-D-galactofuranoside
• Synonyms: methyl 2,3,5-tri-O-benzyl-β-D-galactofuranoside
• CAS NO: 127501-24-0
• Molecular Weight: 464.558
• Mol File: 127501-24-0.mol

Chemical Properties

• CAS DataBase Reference: methyl 2,3,5-tri-O-benzyl-β-D-galactofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3,5-tri-O-benzyl-β-D-galactofuranoside(127501-24-0)
• EPA Substance Registry System: methyl 2,3,5-tri-O-benzyl-β-D-galactofuranoside(127501-24-0)

Safety Data

• Hazardous Substances Data: 127501-24-0(Hazardous Substances Data)

Upstream product

• 1375486-92-2 C₄₇H₄₆O₆ 
• 90244-45-4 methyl 2,3,5,6-tetra-O-acetyl-α/β-D-galactofuranoside 
• 920274-29-9 methyl 2,3,5-tri-O-benzyl-6-O-trityl-β-D-galactofuranoside 

Downstream Products

• 920274-31-3 methyl 2,3-di-O-acetyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside 
• 920274-33-5 methyl 2,3-di-O-benzyl-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside 
• 920274-32-4 methyl 2,3-di-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside 
• 920274-34-6 methyl 2,3,6-tri-O-benzyl-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside 
• 920274-36-8 methyl 5,6-O-isopropylidene-β-D-galactofuranosyl-(1->5)-2,3,6-tri-O-benzyl-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside 
• 920274-35-7 methyl 2,3-di-O-acetyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->5)-2,3,6-tri-O-benzyl-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside 
• 920274-38-0 methyl 3-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->5)-2,3,6-tri-O-benzyl-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside 
• 290820-17-6 methyl 2,3-di-O-benzyl-5,6,7,8-tetradeoxy-β-L-arabino-oct-5(E),7-dieno-1,4-furanoside 
• 290820-11-0 (E)-(R)-4-Benzyloxy-4-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-methoxy-tetrahydro-furan-2-yl)-but-2-en-1-ol 

Relevant articles and documents

Synthetic UDP-galactofuranose analogs reveal critical enzyme-substrate interactions in GlfT2-catalyzed mycobacterial galactan assembly

Mycobacterial cell wall galactan, composed of alternating β-(1→5) and β-(1→6) galactofuranosyl residues, is assembled by the action of two bifunctional galactofuranosyltransferases, GlfT1 and GlfT2, which use UDP-galactofuranose (UDP-Galf) as the donor substrate. Kinetic analysis of synthetic UDP-Galf analogs identified critical interactions involved in donor substrate recognition by GlfT2, a processive polymerizing glycosyltransferase. Testing of methylated UDP-Galf analogs showed the donor substrate-binding pocket is sterically crowded. Evaluation of deoxy UDP-Galf analogs revealed that the C-6 hydroxyl group is not essential for substrate activity, and that interactions with the UDP-Galf C-3 hydroxyl group orient the substrate for turnover but appears to play no role in substrate recognition, making the 3-deoxy-analog a moderate competitive inhibitor of the enzyme. Moreover, the addition of a Galf residue deoxygenated at C-5 or C-6, or an l-arabinofuranose residue, to the growing galactan chain resulted in "dead end" reaction products, which no longer act as an acceptor for the enzyme. This finding shows dual recognition of both the terminal C-5 and C-6 hydroxyl groups of the acceptor substrate are required for GlfT2 activity, which is consistent with a recent model developed based upon a crystal structure of the enzyme. These observations provide insight into specific protein-carbohydrate interactions in the GlfT2 active site and may facilitate the design of future inhibitors.

Synthesis of a pentasaccharide fragment of varianose, a cell wall polysaccharide from Penicillium varians

The first synthesis of an oligosaccharide fragment of varianose, a polysaccharide produced by Penicillium varians, is reported. The target pentasaccharide features both α- and β-galactofuranoside residues and the α-galactofuranoside residue is hindered, b