98807-72-8

Upstream product

• 180336-13-4 8-methoxycarbonyloctyl 3,4,6-tri-O-benzyl-2-O-(methylthio)thiocarbonyl-β-D-galactopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 98807-70-6 8-methoxycarbonyloctyl 2-acetamido-3-O-(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 84439-23-6 2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl bromide 
• 180336-12-3 8-methoxycarbonyloctyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 98856-37-2 8-methoxycarbonyloctyl 3,4,6-tri-O-benzyl-β-D-galactopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 71048-95-8 ω-methoxycarbonyloctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 77790-47-7 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl bromide 
• 98807-71-7 8-methoxycarbonyoctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(3,4,6-tri-O-benzyl-2-O-phenoxythiocarbonyl-β-D-galactopyranosyl)-β-D-glucopyranoside 

Relevant academic research and scientific papers

Recognition of β-D-Gal p-(1 → 3)-β-D-Glc pNAc-OR acceptor analogues by the Lewis α-(1 → 3/4)-fucosyltransferase from human milk

The Lewis α-(1 → 3/4)-fucosyltransferase (E.C. 2.4.1.65) transfers L-fucose from GDP-fucose to OH-4 of the Glc pNAc residue in the disaccharide β-D-Gal p(1 → 3)-β-D-Glc pNAc-OR [R = (CH2)8COOMe] (1) to give the Lewis-A blood group determinant β-D-Gal p-(1 → 3)-[α-L-Fuc p-(1 → 4)]-β-D-Glc pNAc-OR. Five deoxy analogues of 1, as well as its N-propionyl derivative, were chemically synthesized and kinetically evaluated as both substrates and inhibitors for the enzyme from human milk. The unmodified acceptor 1 had Km = 640 μM with Vmax set arbitrarily to 100. The 6-deoxy (Km = 400 μM, Vmax = 90) and N-propionyl compounds (Km = 330 μM Vmax = 170) remained excellent substrates while the 4-deoxy compound was a very weak competitive inhibitor with Ki = 9 mM. Deoxygenation of OH-2′ and OH-4′ (of the Gal residue) in 1 had little effect on the activity. The OH-6 group of the Gal residue proved to be critical for recognition by the enzyme since substitution of this group with hydrogen led to an inactive compound.

THE SYNTHESIS OF MONODEOXY DERIVATIVES OF LACTO-N-BIOSE I AND N-ACETYL-LACTOSAMINE TO SERVE AS SUBSTRATES FOR THE DIFFERENTIATION OF α-L-FUCOSYL TRANSFERASES

The chemical synthesis of β-D-Gal-(1->3)-4-deoxy-β-D-GlcNAcOR and β-D-Gal-(1->4)-3-deoxy-β-D-GlcNAcOR, wherein R = (CH2)8COOMe and Me, are reported.Also, 2-deoxy-β-D-Gal-(1->3)-β-D-GlcNAcO(CH2)8COOMe and 2-deoxy-β-D-Gal-(1->4)-β-D-GlcNAcO(CH2)8COOMe were