beta-D-Gal-(1->4)-beta-D-GlcNAc-(1->3)-beta-D-Gal-(1->4)-D-Glc

Base Information

• Chemical Name: beta-D-Gal-(1->4)-beta-D-GlcNAc-(1->3)-beta-D-Gal-(1->4)-D-Glc
• CAS No.: 13007-32-4
• Molecular Formula: C₂₆H₄₅NO₂₁
• Molecular Weight: 707.637
• Hs Code.: 29400090
• European Community (EC) Number: 815-162-5
• Nikkaji Number: J510.844F
• Wikidata: Q27127149
• Metabolomics Workbench ID: 61025
• Mol file: 13007-32-4.mol

Synonyms:lacto-N-neotetraose;lacto-N-tetraose;LNnT;N-neotetraose

Chemical Property of beta-D-Gal-(1->4)-beta-D-GlcNAc-(1->3)-beta-D-Gal-(1->4)-D-Glc

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1173.6°Cat760mmHg
• Flash Point: 663.6°C
• PSA: 356.70000
• Density: 1.72g/cm³
• LogP: -9.21410
• Storage Temp.: 2-8°C
• Solubility.: Water (Slightly), Methanol (Slightly, Heated)
• XLogP3: -8.5
• Hydrogen Bond Donor Count: 14
• Hydrogen Bond Acceptor Count: 21
• Rotatable Bond Count: 11
• Exact Mass: 707.24840744
• Heavy Atom Count: 48
• Complexity: 1030

Purity/Quality:

≥95% ^*data from raw suppliers

Lacto-N-neotetraose ^*data from reagent suppliers

Safty Information:

• Hazard Codes: B
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1OC2C(C(OC(C2O)OC3C(OC(C(C3O)O)O)CO)CO)O)CO)OC4C(C(C(C(O4)CO)O)O)O)O
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1O[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)O)CO)CO)O)CO)O[C@H]4[C@@H]([C@H]([C@H]([C@H](O4)CO)O)O)O)O
• Uses: Lacto-N-neotetraose (CAS# 13007-32-4) is a polysaccaride found in human milk. Oral supplementation of lacto-N-neotetraose in healthy adults resulted in shifts the intestinal microbiota - a substantial increase in relative abundance of actinobacteria and bifidobacterium and a reduction in the abundance of firmicutes and proteobacteria.

Technology Process of beta-D-Gal-(1->4)-beta-D-GlcNAc-(1->3)-beta-D-Gal-(1->4)-D-Glc

There total 26 articles about beta-D-Gal-(1->4)-beta-D-GlcNAc-(1->3)-beta-D-Gal-(1->4)-D-Glc 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: 99.0%

D-Galactose (10257-28-0) + O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-(β-D-galactopyranosyl)-(1->4)-D-glucopyranoside (75645-27-1) → lacto-N-neo-tetraose (86594-19-6,115216-11-0,13007-32-4)

Guidance literature:

With Pasteurella multocida inorganic pyrophosphatase; Bifidobacterium longum UDP-sugar pyrophosphorylase; Escherichia coli galactokinase; Neisseria meningitidis β1?4-galactosyltransferase; UTP; ATP; magnesium chloride; In aq. buffer; at 37 ℃; for 30h; pH=8.0; Enzymatic reaction;

DOI:10.1021/acs.joc.6b01905

Reference yield: 92.0%

benzyl O-(3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1→4)-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1→3)-O-(4-O-benzyl-β-D-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside → lacto-N-neo-tetraose (86594-19-6,115216-11-0,13007-32-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethanol; water; at 20 ℃;

DOI:10.1016/j.carres.2019.107743

Reference yield: 91.0%

acetyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2-acetamido-4,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α,β-D-glucopyranoside (118700-97-3,121839-48-3,121839-49-4) → lacto-N-neo-tetraose (86594-19-6,115216-11-0,13007-32-4)

Guidance literature:

With amberlite IR 120 (H⁺ form); sodium methylate; In methanol; for 72h; Ambient temperature;

DOI:10.1016/S0008-6215(99)00051-8

upstream raw materials:

uridine 5'-diphospho-D-galactose

O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-(β-D-galactopyranosyl)-(1->4)-D-glucopyranoside

acetyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2-acetamido-4,6-di-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->3)-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α,β-D-glucopyranoside

C₃₆H₅₉N₃O₂₂

Downstream raw materials:

(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2-6)-β-D-galactopyranosyl-(1-4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1-3)-β-D-galactopyranosyl-(1-4)-α,β-D-glucopyranoside

(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2-3)-β-D-galactopyranosyl-(1-4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1-3)-β-D-galactopyranosyl-(1-4)-α,β-D-glucopyranose

Refernces

• 1、 Bandara, Mithila D.,Stine, Keith J.,Demchenko, Alexei V.. "The chemical synthesis of human milk oligosaccharides: Lacto-N-neotetraose (Galβ1→4GlcNAcβ1→3Galβ1→4Glc)". . . Retrieved 2019/07/17.
• 2、 Wei, Mohui,McKitrick, Tanya R.,Mehta, Akul Y.,Gao, Chao,Jia, Nan,McQuillan, Alyssa M.,Heimburg-Molinaro, Jamie,Sun, Lijun,Cummings, Richard D.. "Novel Reversible Fluorescent Glycan Linker for Functional Glycomics". . p. 2897 - 2908. Retrieved 2019/11/11.