3-Sialyl-N-acetyllactosamine

Base Information

• Chemical Name: 3-Sialyl-N-acetyllactosamine
• CAS No.: 81693-22-3
• Molecular Formula: C₂₅H₄₂N₂O₁₉
• Molecular Weight: 674.61
• Hs Code.: 29400090
• DSSTox Substance ID: DTXSID90583978
• Metabolomics Workbench ID: 38951
• Mol file: 81693-22-3.mol

Synonyms:3-Sialyl-N-acetyllactosamine;102490-37-9;(2R,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R)-6-acetamido-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid;3/'-SIALYL-N-ACETYLLACTOSAMINE;SCHEMBL21594811;DTXSID90583978;CHEBI:190875;3'-Sialyl-N-acetyllactosamine, Na salt, >=90% (TLC);(2R,4S,5R,6R)-5-acetamido-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R)-6-acetamido-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid;O-(N-acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-D-Glucose;O-(N-acetyl-alpha-neuraminosyl)-(2->3)-O-beta-delta-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-delta-Glucose

Chemical Property of 3-Sialyl-N-acetyllactosamine

Chemical Property:

• Boiling Point: 1190.4oC at 760 mmHg
• Flash Point: 673.8oC
• PSA: 346.78000
• Density: 1.7g/cm3
• LogP: -8.63250
• Storage Temp.: −20°C
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -7.2
• Hydrogen Bond Donor Count: 13
• Hydrogen Bond Acceptor Count: 19
• Rotatable Bond Count: 12
• Exact Mass: 674.23817711
• Heavy Atom Count: 46
• Complexity: 1050

Purity/Quality:

99%, ^*data from raw suppliers

3''-α-Sialyl-N-acetyllactosamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(CC(OC1C(C(CO)O)O)(C(=O)O)OC2C(C(OC(C2O)OC3C(OC(C(C3O)O)NC(=O)C)CO)CO)O)O
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H](C[C@](O[C@H]1[C@@H]([C@@H](CO)O)O)(C(=O)O)O[C@H]2[C@H]([C@H](O[C@H]([C@@H]2O)O[C@@H]3[C@H](OC([C@@H]([C@H]3O)O)NC(=O)C)CO)CO)O)O
• Uses: 3''-α-Sialyl-N-acetyllactosamine (cas# 81693-22-3) is a compound useful in organic synthesis. It is used with immunomodulatory oligosaccharides for treatment of viral respiratory infection.

Technology Process of 3-Sialyl-N-acetyllactosamine

There total 3 articles about 3-Sialyl-N-acetyllactosamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

uridine 5'-diphospho-D-galactose (2956-16-3) → Neu5Acα(2-3)Galβ(1-4)GlcNAc (102490-37-9,210418-18-1,81693-22-3)

Guidance literature:

Multi-step reaction with 2 steps

1: β1–4-galactosyltransferase from Neisseria meningitidis / Enzymatic reaction

2: magnesium(II); Pasteurella multocida α2,3-sialyltransferase; Neisseria meningitides CMP-Sia synthetase; cytidine triphosphate / aq. buffer / pH 7.5 / Enzymatic reaction

With β1–4-galactosyltransferase from Neisseria meningitidis; Neisseria meningitides CMP-Sia synthetase; Pasteurella multocida α2,3-sialyltransferase; magnesium(II); cytidine triphosphate; In aq. buffer;

DOI:10.1021/jacs.6b07132

Reference yield:

2-acetamido-2-deoxy-D-glucose (7512-17-6,282727-46-2,478518-83-1,127959-06-2,78393-48-3) → Neu5Acα(2-3)Galβ(1-4)GlcNAc (102490-37-9,210418-18-1,81693-22-3)

Guidance literature:

Multi-step reaction with 2 steps

1: β1–4-galactosyltransferase from Neisseria meningitidis / Enzymatic reaction

2: magnesium(II); Pasteurella multocida α2,3-sialyltransferase; Neisseria meningitides CMP-Sia synthetase; cytidine triphosphate / aq. buffer / pH 7.5 / Enzymatic reaction

With β1–4-galactosyltransferase from Neisseria meningitidis; Neisseria meningitides CMP-Sia synthetase; Pasteurella multocida α2,3-sialyltransferase; magnesium(II); cytidine triphosphate; In aq. buffer;

DOI:10.1021/jacs.6b07132

Reference yield:

N-Acetylneuraminic acid (131-48-6,14752-56-8,5977-25-3,6225-16-7,6918-20-3) + N-acetyllactosamine (32181-59-2,50787-11-6,82441-98-3,85441-65-2) → Neu5Acα(2-3)Galβ(1-4)GlcNAc (102490-37-9,210418-18-1,81693-22-3)

Guidance literature:

With Neisseria meningitides CMP-Sia synthetase; Pasteurella multocida α2,3-sialyltransferase; magnesium(II); cytidine triphosphate; In aq. buffer; pH=7.5; Enzymatic reaction;

DOI:10.1021/jacs.6b07132

upstream raw materials:

N-Acetylneuraminic acid

N-acetyllactosamine

uridine 5'-diphospho-D-galactose

2-acetamido-2-deoxy-D-glucose

Refernces