89824-83-9

Upstream product

• 67670-69-3 N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 
• 89733-63-1 Benzyl-O-(methyl-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-didesoxy-D-glycero-β-D-galacto-2-nonulopyranosyl)onat)-(2->6)-O-(2,3-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2-amino-3,6-di-O-benzyl-2-desoxy-β-D-glucopyranosid-dihydrogensulfid 
• 89733-64-2 Benzyl-O-(methyl-(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-didesoxy-D-glycero-β-D-galacto-2-nonulopyranosyl)onat)-(2->6)-O-(4-O-acetyl-2,3-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-desoxy-β-D-glucopyranosid 
• 108740-39-2 (1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate 
• 19342-36-0 2,4,7,8,9-Penta-O-acetyl-N-acetyl-β-D-neuraminsaeure 
• 4307-58-8 N-acetyl-D-lactosamine 
• 89733-66-4 Benzyl-O-(5-acetamido-3,5-didesoxy-D-glycero-β-D-galacto-2-nonulopyranosylonsaeure)-(2->6)-O-(2,3-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-desoxy-β-D-glucopyranosid 
• 85750-97-6 Benzyl-2-azido-3,6-di-O-benzyl-2-desoxy-4-O-(2,3-di-O-benzyl-4,6-O-benzyliden-β-D-galactopyranosyl)-β-D-glucopyranosid 
• 85750-98-7 Benzyl-2-azido-3,6-di-O-benzyl-2-desoxy-4-O-(2,3-di-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranosid 
• 81243-72-3 Benzyl-3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-azido-2-desoxy-β-D-glucopyranosid 
• 85750-96-5 Benzyl-2-azido-4-O-(4,6-O-benzyliden-β-D-galactopyranosyl)-2-desoxy-β-D-glucopyranosid 
• 81243-73-4 benzyl 2-azido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranoside 
• 68733-24-4 O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl bromide 
• 67670-69-3 methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosylonate chloride 

Relevant academic research and scientific papers

A novel three-enzyme reaction cycle for the synthesis of N-acetyllactosamine with in situ regeneration of uridine 5'-diphosphate glucose and uridine 5'-diphosphate galactose

A new three-enzyme reaction cycle consisting of sucrose synthase, UDP glucose 4'-epimerase, and human β-1,4-galactosyltransferase was established for the synthesis of N-acetyllactosamine (LacNAc) with in situ regeneration of UDP galactose. We found that UDP glucose 4'-epimerase is reductively inactivated in the presence of UMP and acceptor substrates of β-1,4-galactosyltransferase. Reactivation of UDP glucose 4'-epimerase by the transition state analogues dUDP or dTDP 6-deoxy-D-xylo-4-hexulose in combination with the repetitive batch technique enabled us to use the native enzymes for 11 days in this cycle. With 10 U of sucrose synthase, 5 U of UDP glucose 4'-epimerase, and 1.25 U of β-1,4-galactosyltransferase, 594 mg of LacNAc could be synthesized. N-Acetyllactosamine was also subsequently converted to Neu5Acα2,6Ga1β1,4GlcNAc with α-2,6-sialyltransferase and CMP-Neu5Ac.

SYNTHESE EINES TRISACCHARIDES AUS N-ACETYLNEURAMINSAEURE UND N-ACETYLLACTOSAMIN

The reaction of methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-chloro-2,3,5-trideoxy-D-glycero-β-D-galacto-2-nonulopyranosonate with benzyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3-di-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside in the presence of mercury cyanide-mercuri bromide gave a 1:1 mixture of the two anomeric (2->6)linked trisaccharides containing N-acetylneuraminic acid.By chromatography, 22percent of benzyl O-(methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2->6)-O-(2,3-di-O-benzyl-β-D-galactopyranosyl)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside and 23percent of the corresponding β-(2->6)-linked isomer could be isolated.A deblocking sequence, consisting of hydrogen sulfide reduction, acetylation, deacetylation, ester hydrolysis and hydrogenolysis led to the deblocked O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->6)-O-β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-D-glucopyranose and to the corresponding β-(2->6)-linked compound.