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

Description

LACTO-N-NEOTETRAOSE, with the CAS number 13007-32-4, is a tetrasaccharide composed of galactose, N-acetylglucosamine, galactose, and glucose in a linear sequence, all connected by beta-linkages. It is a polysaccharide naturally found in human milk and is known for its beneficial effects on the intestinal microbiota.
Used in Pharmaceutical Industry:
LACTO-N-NEOTETRAOSE is used as a dietary supplement for promoting a healthy gut microbiota. The application reason is that oral supplementation of LACTO-N-NEOTETRAOSE in healthy adults has been shown to result in shifts in the intestinal microbiota, with a substantial increase in the relative abundance of actinobacteria and bifidobacterium, and a reduction in the abundance of firmicutes and proteobacteria.
Used in Nutritional Supplements:
LACTO-N-NEOTETRAOSE is used as an ingredient in nutritional supplements for supporting gut health. The application reason is its ability to positively influence the gut microbiota composition, which is essential for overall health and well-being.
Used in Infant Formula:
LACTO-N-NEOTETRAOSE is used as an additive in infant formula to mimic the natural composition of human milk. The application reason is to provide infants with the same health benefits associated with the presence of LACTO-N-NEOTETRAOSE in breast milk, such as improved gut health and immune system support.
Chemical Properties:
LACTO-N-NEOTETRAOSE is a white freeze-dried powder, which makes it suitable for incorporation into various formulations and products.

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 
• 250224-51-2 C₃₆H₅₉N₃O₂₂ 
• 133-89-1 UDP-glucose 
• 679828-92-3 N-{(2S,3R,4R,5S,6R)-2-[(2S,3R,4S,5S,6R)-2-((2R,3S,4R,5R,6S)-4,5-Dihydroxy-2-hydroxymethyl-6-mercapto-tetrahydro-pyran-3-yloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl}-acetamide 
• 2592-37-2 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranose 
• 252665-92-2 bis[β-D-galactopyranosyl-(1-4)-1-thio-β-D-glucopyranosyl]1,1'-disulfide 
• 50611-42-2 β-D-galactopyranosyl-(1->4)-1-thio-β-D-glucopyranoside 
• 679828-91-2 bis[2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl] disulfide 
• 91926-84-0 β-lactosylamine 
• 250224-46-5 lactose-squaric acid conjugate 
• 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 
• 250224-50-1 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 

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.

Biochemical characterization of Helicobacter pylori α1–3-fucosyltransferase and its application in the synthesis of fucosylated human milk oligosaccharides

Fucosylated human milk oligosaccharides (HMOs) have important biological functions. Enzymatic synthesis of such compounds requires robust fucosyltransferases. A C-terminal 66-amino acid truncated version of Helicobacter pylori α1–3-fucosyltransferase (Hp3FT) is a good candidate. Hp3FT was biochemically characterized to identify optimal conditions for enzymatic synthesis of fucosides. While N-acetyllactosamine (LacNAc) and lactose were both suitable acceptors, the former is preferred. At a low guanosine 5′-diphospho-β-L-fucose (GDP-Fuc) to acceptor ratio, Hp3FT selectively fucosylated LacNAc. Based on these enzymatic characteristics, diverse fucosylated HMOs, including 3-fucosyllactose (3-FL), lacto-N-fucopentaose (LNFP) III, lacto-N-neofucopentaose (LNnFP) V, lacto-N-neodifucohexaose (LNnDFH) II, difuco- and trifuco-para-lacto-N-neohexaose (DF-paraLNnH and TF-para-LNnH), were synthesized enzymatically by varying the ratio of the donor and acceptor as well as controlling the order of multiple glycosyltransferase-catalyzed reactions.

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.