86594-19-6

Basic information

• Product Name: lacto-N-neo-tetraose
• CAS NO: 86594-19-6
• Molecular Weight: 707.637
• Mol File: 86594-19-6.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: lacto-N-neo-tetraose(CAS DataBase Reference)
• NIST Chemistry Reference: lacto-N-neo-tetraose(86594-19-6)
• EPA Substance Registry System: lacto-N-neo-tetraose(86594-19-6)

Safety Data

• Hazardous Substances Data: 86594-19-6(Hazardous Substances Data)

Upstream product

• 75645-27-1 O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-(β-D-galactopyranosyl)-(1->4)-D-glucopyranoside 
• 7349-77-1 uridine 5'-diphospho-β-D-galactose 
• 68124-21-0 C₃₁H₄₉NO₂₀ 
• 10257-28-0 D-Galactose 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 68124-22-1 1-O-benzyl-β-lacto-N-neotetraose 
• 1329426-63-2 C₃₃H₄₈Cl₃NO₂₁ 
• 250224-50-1 N-(2-{2-[6-(2-hexylamino-3,4-dioxo-cyclobut-1-enylamino)-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy}-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-acetamide 
• 250224-49-8 3-[(2R,3R,4R,5S,6R)-3,4-Dihydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylamino]-4-hexylamino-cyclobut-3-ene-1,2-dione 
• 250224-46-5 lactose-squaric acid conjugate 
• 91926-84-0 β-lactosylamine 
• 679828-91-2 bis[2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl] disulfide 
• 50611-42-2 β-D-galactopyranosyl-(1->4)-1-thio-β-D-glucopyranoside 
• 252665-92-2 bis[β-D-galactopyranosyl-(1-4)-1-thio-β-D-glucopyranosyl]1,1'-disulfide 

Downstream Products

• 100789-83-1 (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 
• 64003-55-0 (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 

Relevant articles and documents

Reversible derivatization of sugars with carbobenzyloxy groups and use of the derivatives in solution-phase enzymatic oligosaccharide synthesis

Simple protocols for attaching and detaching carbobenzyloxy (Cbz) groups at the reducing end of sugars was developed. Briefly, lactose was converted into its glycosylamine, which was then acylated with carbobenzyloxy chloride in high overall yield. The obtained lactose Cbz derivative was used in sequential glycosylations using glycosyltransferases and nucleotide sugars in aqueous buffers. Isolation of the reaction products after each step was by simple C-18 solid-phase extraction. The Cbz group was removed by catalytic hydrogenolysis or catalytic transfer hydrogenation followed by in situ glycosylamine hydrolysis. In this way, a trisaccharide (GlcNAc-lactose), a human milk tetrasaccharide (LNnT), and a human milk pentasaccharide (LNFPIII) were prepared in a simple and efficient way.

The chemical synthesis of human milk oligosaccharides: Lacto-N-neotetraose (Galβ1→4GlcNAcβ1→3Galβ1→4Glc)

The discovery of innovative methods that offer new capabilities for obtaining individual oligosaccharides from human milk will help to improve understanding their roles and boost practical applications. The total chemical synthesis of lacto-N-neotetraose

Sequential One-Pot Multienzyme Chemoenzymatic Synthesis of Glycosphingolipid Glycans

Glycosphingolipids are a diverse family of biologically important glycolipids. In addition to variations on the lipid component, more than 300 glycosphingolipid glycans have been characterized. These glycans are directly involved in various molecular recognition events. Several naturally occurring sialic acid forms have been found in sialic acid-containing glycosphingolipids, namely gangliosides. However, ganglioside glycans containing less common sialic acid forms are currently not available. Herein, highly effective one-pot multienzyme (OPME) systems are used in sequential for high-yield and cost-effective production of glycosphingolipid glycans, including those containing different sialic acid forms such as N-acetylneuraminic acid (Neu5Ac), N-glycolylneuraminic acid (Neu5Gc), 2-keto-3-deoxy-d-glycero-d-galacto-nononic acid (Kdn), and 8-O-methyl-N-acetylneuraminic acid (Neu5Ac8OMe). A library of 64 structurally distinct glycosphingolipid glycans belonging to ganglio-series, lacto-/neolacto-series, and globo-/isoglobo-series glycosphingolipid glycans is constructed. These glycans are essential standards and invaluable probes for bioassays and biomedical studies.