32181-59-2

Basic information

• Product Name: N-ACETYLLACTOSAMINE
• Synonyms: Glucopyranose Galf1-b-4-GlcNAc;2-Acetamido-2-deoxy-4-O-D-galactopyranosyl-D-glucopyranose, N-Acetyl-4-O-(D-galactopyranosyl)-D-glucosamine;2-Acetamido-2-deoxy-4-O--D-galactopyranosyl-D-glucopyranose;Gal-(1-4)-D-GlcNAc;β-D-Gal-(1-4)-D-GlcNAc, LN, 2-Acetamido-2-deoxy-4-O-β-D-galactopyranosyl-D-glucopyranose, N-Acetyl-4-O-(β-D-galactopyranosyl)-D-glucosamine;2-Acetylamino-4-O-β-D-galactopyranosyl-2-deoxy-D-glucopyranose;4-O-(β-D-Galactopyranosyl)-2-(acetylamino)-2-deoxy-D-glucopyranose;4-O-(β-D-Galactopyranosyl)-2-acetylamino-2-deoxy-D-glucopyranose
• CAS NO: 32181-59-2
• Molecular Formula: C₁₄H₂₅NO₁₁
• Molecular Weight: 383.35
• Product Categories: Oligosaccharides;Carbohydrates
• Mol File: 32181-59-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: 191-192
• Boiling Point: 805.5 °C at 760 mmHg
• Flash Point: 441 °C
• Appearance: White Crystalline Solid
• Density: 1.64 g/cm³
• Vapor Pressure: 5.02E-30mmHg at 25°C
• Refractive Index: 1.623
• Storage Temp.: −20°C
• Solubility: H2O: 10 mg/mL, clear, colorless
• PKA: 12.85±0.20(Predicted)
• Stability: Hygroscopic
• BRN: 96808
• CAS DataBase Reference: N-ACETYLLACTOSAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-ACETYLLACTOSAMINE(32181-59-2)
• EPA Substance Registry System: N-ACETYLLACTOSAMINE(32181-59-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 32181-59-2(Hazardous Substances Data)

Usage

Description

N-Acetyllactosamine, also known as N-Acetyl-D-lactosamine, is a white crystalline solid that serves as a crucial component in the oligosaccharide portion of many Nand O-linked glycoproteins. It is a fundamental building unit for the antigenic determinants of certain human blood group activities and the ABH Type 2 determinants.

Uses

Used in Biochemical Research:
N-Acetyllactosamine is used as a component in the oligosaccharide portion of glycoproteins, playing a vital role in the study of structural space of the Galectin-1-Ligand interaction. It is also utilized to identify impurities as imidazoline ring structures.
Used in Glycobiology and Lectin Studies:
N-Acetyllactosamine is employed as a specific lectin target molecule in the identification and differentiation of sugar-binding molecules, such as the galectins. It is also used in research involving galactosidase, fucosyltransferase, sialyltransferase, and lectin inhibition.
Used in the Development of Antigen Determinants:
N-Acetyllactosamine is a key building unit for the antigenic determinants of certain human blood group activities and the ABH Type 2 determinants, making it essential in the development and study of these antigens.
Used in Pharmaceutical and Diagnostic Applications:
Due to its role in the formation of oligosaccharides and its interaction with lectins, N-Acetyllactosamine has potential applications in the development of pharmaceuticals and diagnostic tools targeting glycoprotein-related diseases and conditions.

Purification Methods

Purify N-acetyl-D-lactosamine by recrystallisation from MeOH (with 1 mol of MeOH) or from H2O. It is available commercially as a solution of 0.5g/mL of H2O. [Zilliken J Biol Chem 271 181 1955, Beilstein 17 IV 3452.]

InChI:InChI=1/C14H25NO11/c1-4(18)15-7-9(20)12(6(3-17)24-13(7)23)26-14-11(22)10(21)8(19)5(2-16)25-14/h5-14,16-17,19-23H,2-3H2,1H3,(H,15,18)

Synthetic route

2-acetamido-2-deoxy-D-glucose (7512-17-6) + 4-nitrophenyl-β-D-galactopyranoside (3150-24-1) → β-Galp-(1->6)-GlcNAc (13071-21-1, 34621-78-8, 50787-10-5, 58650-61-6, 72142-81-5, 72521-11-0, 84730-38-1, 109446-44-8, 119870-65-4) + N-acetyllactosamine (32181-59-2)

Conditions	Yield
With Biolacta N5 In 2-hydroxy-1,3-dioxane at 30℃; pH=5; aq. buffer; Enzymatic reaction; regioselective reaction;	A 91% B 9%
With Biolacta N5 at 30℃; pH=5; aq. buffer; Enzymatic reaction; regioselective reaction;	A 17% B 83%

O4-β-D-galactopyranosyl-D-arabino-[2]hexosulose-bis-phenylhydrazone (4746-17-2, 4746-19-4, 4746-20-7, 118634-17-6) → N-acetyllactosamine (32181-59-2)

Conditions	Yield
With palladium on activated charcoal; ethanol; acetic acid Hydrogenation.Behandlung des Reaktionsprodukts mit Acetanhydrid, Pyridin und wenig Triaethylamin und anschliessend mit Ammoniak in Methanol;

O3-β-D-galactopyranosyl-D-arabinose-phenylimine → N-acetyllactosamine (32181-59-2)

Conditions	Yield
With hydrogen cyanide; N,N-dimethyl-formamide Hydrieren des Reaktionsprodukts an Palladium/Bariumsulfat in wss. Salzsaeure und Behandeln mit Acetanhydrid, Natriumacetat und wss. Methanol;

3-O-β-D-galactopyranosyl-D-arabinose (6057-48-3) → N-acetyllactosamine (32181-59-2)

D-(+)-lactose (63-42-3) + N-acetyl-D-glucosamine → N-acetyllactosamine (32181-59-2)

Conditions	Yield
With lactobacillus-bifidus-cultures

uridine 5'-diphospho-D-galactose (2956-16-3) + 2-acetamido-2-deoxy-D-glucose (7512-17-6) → N-acetyllactosamine (32181-59-2)

Conditions	Yield
With β1–4-galactosyltransferase from Neisseria meningitidis Enzymatic reaction;

N-acetyllactosamine (32181-59-2) → 2-acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-D-glucitol (62397-86-8)

Conditions	Yield
With sodium tetrahydroborate In water for 24h;	99.7%
With sodium tetrahydroborate In water at 25℃; for 6h; reduction;

N-acetyllactosamine (32181-59-2) → N-acetyllactosamine methyl glycoside (68774-40-3)

Conditions	Yield
With methanol; water; diazomethane diethyl ether

N-acetyllactosamine (32181-59-2) → 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-deoxy-2-acetamido-1,3,4-tri-O-acetyl-α-D-glucopyranose (36954-63-9)

Conditions	Yield
With pyridine; acetic anhydride

N-acetyllactosamine (32181-59-2) → 4-acetamido-4-deoxy-2-O-(β-D-galactopyranosyl)-L-xylose (154859-30-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 99.7 percent / NaBH4 / H2O / 24 h 2: 92 percent / lead tetraacetate, acetic acid / dimethylsulfoxide / 1 h / -30 °C View Scheme

N-(aminoethyl)-4-(aminooxymethyl)benzamide hydrochloride + N-acetyllactosamine (32181-59-2) → C24H38N4O12 + C24H38N4O12

Conditions	Yield
at 37℃; pH=4.5; aq. acetate buffer;

N-(2-aminoethyl)-4-[(methylaminooxy)methyl]benzamide hydrochloride + N-acetyllactosamine (32181-59-2) → (M-AMB)LacNAc

Conditions	Yield
at 37℃; pH=4.5; aq. acetate buffer;

N-(2-aminoethyl)-4-[(benzylaminooxy)methyl]benzamide hydrochloride + N-acetyllactosamine (32181-59-2) → (B-AMB)LacNAc

Conditions	Yield
at 37℃; pH=4.5; aq. acetate buffer;

N-Acetylneuraminic acid (131-48-6) + N-acetyllactosamine (32181-59-2) → Neu5Acα(2-3)Galβ(1-4)GlcNAc

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

N-Acetylneuraminic acid (131-48-6) + N-acetyllactosamine (32181-59-2) → C25H42N2O19

Conditions	Yield
With α2,6-sialyltransferase from Photobacterium damsel; Neisseria meningitides CMP-Sia synthetase; magnesium(II); cytidine triphosphate In aq. buffer pH=7.5; Enzymatic reaction;

N-acetyllactosamine (32181-59-2) → β-N-acetyllactosaminylamine (163559-38-4)

Conditions	Yield
With ammonium hydroxide; ammonium carbamate In methanol at 37℃; for 24h;

Upstream product

• 4746-17-2 O⁴-β-D-galactopyranosyl-D-arabino-[2]hexosulose-bis-phenylhydrazone 
• 6057-48-3 3-O-β-D-galactopyranosyl-D-arabinose 
• 63-42-3 D-(+)-lactose 
• 7512-17-6 2-acetamido-2-deoxy-D-glucose 
• 3150-24-1 4-nitrophenyl-β-D-galactopyranoside 
• 2956-16-3 uridine 5'-diphospho-D-galactose 

Downstream Products

• 36954-63-9 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-deoxy-2-acetamido-1,3,4-tri-O-acetyl-α-D-glucopyranose 
• 102490-37-9 Neu5Acα(2-3)Galβ(1-4)GlcNAc 

Relevant articles and documents

Two-Step Chemoenzymatic Detection of N-Acetylneuraminic Acid-α(2-3)-Galactose Glycans

Sialic acids are typically linked α(2-3) or α(2-6) to the galactose that located at the non-reducing terminal end of glycans, playing important but distinct roles in a variety of biological and pathological processes. However, details about their respective roles are still largely unknown due to the lack of an effective analytical technique. Herein, a two-step chemoenzymatic approach for the rapid and sensitive detection of N-acetylneuraminic acid-α(2-3)-galactose glycans is described.