197655-20-2

Upstream product

• 115479-43-1 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl chloride 
• 118249-72-2 octyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside 

Downstream Products

• 197655-24-6 N-{(2S,3R,4R,5S,6R)-2-[(2S,3S,4S,5R,6R)-5-Azido-4-benzyloxy-6-methyl-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide 
• 197655-22-4 C₆₈H₈₀N₄O₁₈ 
• 197655-21-3 (2S,3S,4S,5R,6R)-5-Azido-4-benzyloxy-6-methyl-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-octyloxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-3-ol 

Relevant academic research and scientific papers

Synthesis and evaluation of eight aminodeoxy trisaccharide inhibitors for N-acetylglucosaminyltransferase-V

N-Acetylglucosaminyltransferase-V is an important enzyme controlling the branching pattern of N-linked oligosaccharides. This enzyme recognizes the trisaccharide octyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1 → 2)-α-D-mannopyranosyl-(1 → 6)-β-D-glucopyranoside (5) as a substrate and adds a β-linked GlcNAc residue to OH-6 of the central α-Man unit. Eight analogs of 5 were chemically synthesized where C-6 of the α-Man residue in 5 was deoxygenated, and structurally diverse modifications were introduced at C-4 of the same residue. The key intermediate prepared for this purpose was octyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1 → 2)-4-amino-4,6-dideoxy-α-D-mannopyranosyl-(1 → 6)-β-D-glucopyranoside (7a) where the original 4'-amino group was readily derivatized on the unprotected sugar. The eight analogs 7a-7h were evaluated as inhibitors for GlcNAcT-V, both isolated (from hamster kidney) and cloned (from rat kidney). All of the compounds were found to be competitive inhibitors with K(i) in the range of 3-106 μM. The conclusion of this work is that recognition of acceptor 5 does not involve contact of the C-6-C-4 end of the α-Man residue with the protein in the E-I (or E-S) complex.