180471-91-4

Basic information

• Product Name: 8-methoxycarbonyloctyl 6-deoxy-β-D-galactopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
• Synonyms: 8-methoxycarbonyloctyl 6-deoxy-β-D-galactopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
• CAS NO: 180471-91-4
• Molecular Weight: 625.714
• Mol File: 180471-91-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 8-methoxycarbonyloctyl 6-deoxy-β-D-galactopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 8-methoxycarbonyloctyl 6-deoxy-β-D-galactopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside(180471-91-4)
• EPA Substance Registry System: 8-methoxycarbonyloctyl 6-deoxy-β-D-galactopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside(180471-91-4)

Safety Data

• Hazardous Substances Data: 180471-91-4(Hazardous Substances Data)

Upstream product

• 180471-90-3 8-methoxycarbonyloctyl 2,3,4-tri-O-acetyl-6-deoxy-β-D-galactopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 5158-64-5 2,3,4-tri-O-acetyl-D-fucopyranosyl bromide 
• 71048-95-8 ω-methoxycarbonyloctyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 

Relevant articles and documents

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.