13007-32-4

Basic information

• Product Name: LACTO-N-NEOTETRAOSE
• Synonyms: N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxyoxan-4-yl]oxy-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide;Neolactotetraose;LNnT, β-D-Gal-(1-4)-β-D-GlcNAc-(1-3)-β-D-Gal-(1-4)-D-Glc;Lacto-N-neotetraose ,>=95%;β-D-Gal-(1→4)-β-D-GlcNAc-(1→3)-β-D-Gal-(1→4)-D-Glc;LNNT;BETA-D-GAL-[1->4]-BETA-D-GLCNAC-[1->3]-BETA-D-GAL-[1->4]-D-GLC;GAL-BETA1,4GLCNA-CBETA1, 3GAL-BETA1, 4GLC
• CAS NO: 13007-32-4
• Molecular Formula: C26H45NO21
• Molecular Weight: 707.63
• Mol File: 13007-32-4.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 1173.6°Cat760mmHg
• Flash Point: 663.6°C
• Appearance: /
• Density: 1.72g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.668
• Storage Temp.: 2-8°C
• Solubility: Water (Slightly), Methanol (Slightly, Heated)
• Stability: Hygroscopic
• CAS DataBase Reference: LACTO-N-NEOTETRAOSE(CAS DataBase Reference)
• NIST Chemistry Reference: LACTO-N-NEOTETRAOSE(13007-32-4)
• EPA Substance Registry System: LACTO-N-NEOTETRAOSE(13007-32-4)

Safety Data

• Hazard Codes: B
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 13007-32-4(Hazardous Substances Data)

Usage

Chemical Properties

White freeze-dried powder

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.

Definition

ChEBI: A tetrasaccharide comprising residues of galactose, N-acetylglucosamine, galactose and glucose in a linear sequence, all joined by beta-linkages.

InChI:InChI=1/C26H45NO21/c1-6(32)27-11-21(47-25-18(39)15(36)12(33)7(2-28)44-25)13(34)8(3-29)43-24(11)48-22-14(35)9(4-30)45-26(19(22)40)46-20-10(5-31)42-23(41)17(38)16(20)37/h7-26,28-31,33-41H,2-5H2,1H3,(H,27,32)/t7-,8-,9-,10-,11-,12+,13-,14+,15+,16-,17-,18-,19-,20-,21-,22+,23-,24+,25+,26+/m1/s1

Upstream product

• 2956-16-3 uridine 5'-diphospho-D-galactose 
• 75645-27-1 O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-O-(β-D-galactopyranosyl)-(1->4)-D-glucopyranoside 
• 118700-97-3 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 
• 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 

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 

Related news

Pre-clinical safety assessment of the synthetic human milk, nature-identical, oligosaccharide LACTO-N-NEOTETRAOSE (cas 13007-32-4) (LNnT)09/01/2019

Lacto-N-neotetraose (LNnT) is a tetrasaccharide naturally occurring in human breast milk, but not in cow’s milk. The safety data generated on a potential new LNnT ingredient produced by chemical synthesis is presented. Standard in vitro genotoxicity tests were performed. LNnT was also administe...detailed

Syntheses of a series of LACTO-N-NEOTETRAOSE (cas 13007-32-4) clusters using a carbosilane dendrimer scaffold08/31/2019

4-Pentenyl (2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)-(1→4)-(3,6-di-O-acetyl-2-deoxy-2-phthalimido-β-d-glucopyranosyl)-(1→3)-(2,6-di-O-benzoyl-β-d-galactopyranosyl)-(1→4)-2,3,6-tri-O-benzoyl-β-d-glucopyranoside (4) was synthesized by regioselective glycosylation of 4-pentenyl (2,6,-di-...detailed

Synthesis of LACTO-N-NEOTETRAOSE (cas 13007-32-4) and lacto-N-tetraose using the dimethylmaleoyl group as amino protective group08/30/2019

The disaccharide donor O-[2,3,4,6-tetra-O-acetyl-β-d-galactopyranosyl)-(1→4)-3,6-di-O-benzyl-2-deoxy-2-dimethylmaleimido-α,β-d-glucopyranosyl] trichloroacetimidate (7) was prepared by reacting O-(2,3,4,6-tetra-O-acetyl-α-d-galactopyranosyl) trichloroacetimidate with tert-butyldimethylsilyl ...detailed

Enzymatic supported synthesis of LACTO-N-NEOTETRAOSE (cas 13007-32-4) using dendrimeric polyethylene glycol08/29/2019

The lacto-N-neotetraose tetrasaccharide was synthesized on a new dendrimeric support, based on polyethylene glycol. Starting from 1-thio-β-d-lactose, the trisaccharide (2-acetamido-2-deoxy-β-d-glucopyranosyl)-(1 → 3)-O-β-d-galactopyranosyl-(1 → 4)-1-thio-β-d-glucopyranose was obtained usin...detailed

The chemical synthesis of human milk oligosaccharides: LACTO-N-NEOTETRAOSE (cas 13007-32-4) (Galβ1→4GlcNAcβ1→3Galβ1→4Glc)08/28/2019

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 (LNnT) has been completed using both line...detailed

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.

Novel Reversible Fluorescent Glycan Linker for Functional Glycomics

To aid in generating complex and diverse natural glycan libraries for functional glycomics, more efficient and reliable methods are needed to derivatize glycans. Here we present our development of a reversible, cleavable bifunctional linker 3-(methoxyamino)propylamine (MAPA). As the fluorenylmethyloxycarbonate (Fmoc) version (F-MAPA), it is highly fluorescent and efficiently derivatizes free reducing glycans to generate closed-ring derivatives that preserve the structural integrity of glycans. A library of glycans were derivatized and used to generate a covalent glycan microarray using N-hydroxysuccinimide derivatization. The array was successfully interrogated by a variety of lectins and antibodies, demonstrating the importance of closed-ring chemistry. The glycan derivatization was also performed at large scale using milligram quantities of glycans and excess F-MAPA, and the reaction system was successfully recycled up to five times, without an apparent decrease in conjugation efficiency. The MAPA-glycan is also easy to link to protein to generate neoglycoproteins with equivalent glycan densities. Importantly, the MAPA linker can be reversibly cleaved to regenerate free reducing glycans for detailed structural analysis (catch-and-release), often critical for functional studies of undefined glycans from natural sources. The high conjugation efficiency, bright fluorescence, and reversible cleavage of the linker enable access to natural glycans for functional glycomics.

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.