74867-91-7

Basic information

• Product Name: 1-AMINO-1-DEOXY-BETA-D-GALACTOSE
• Synonyms: B-D-GALACTOPYRANOSYLAMINE;BETA-D-GALACTOPYRANOSYLAMINE;BETA-D-GALACTOSYLAMINE;1-AMINO-1-DEOXY-BETA-D-GALACTOSE;1-amino-1-deoxy-B-D-galactose*crystalline;β-d-galactosylamine;1-Amino-1-deoxy-B-D-galactose;NSC 25270
• CAS NO: 74867-91-7
• Molecular Formula: C₆H₁₃NO₅
• Molecular Weight: 179.17
• Product Categories: Carbohydrates & Derivatives
• Mol File: 74867-91-7.mol
• Article Data: 4

Chemical Properties

• Melting Point: 128-133°C
• Boiling Point: 416.4 °C at 760 mmHg
• Flash Point: 205.6 °C
• Appearance: white crystalline solid
• Density: 1.563 g/cm³
• Vapor Pressure: 1.12E-08mmHg at 25°C
• Refractive Index: 1.6
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-AMINO-1-DEOXY-BETA-D-GALACTOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-AMINO-1-DEOXY-BETA-D-GALACTOSE(74867-91-7)
• EPA Substance Registry System: 1-AMINO-1-DEOXY-BETA-D-GALACTOSE(74867-91-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 74867-91-7(Hazardous Substances Data)

Usage

Chemical Properties

White Crystalline Solid

Uses

1-Amino-1-Deoxy-Beta-D-Galactose, a galactose analogue, is used as a competitive inhibitor to help isolate, purify, identify, differentiate and characterize β-D-galactosidase(s) and galactose oxidase(s).

InChI:InChI=1/C6H13NO5/c7-6-5(11)4(10)3(9)2(1-8)12-6/h2-6,8-11H,1,7H2/t2-,3+,4-,5-,6+/m1/s1

Upstream product

• 530-26-7 D-Mannose 
• 10257-28-0 D-Galactose 

Downstream Products

• 74081-16-6 N-Tetradecyl-N-(D-galactopyranosyl)-amine 
• 99695-59-7 N-Tetradecyl-N-(D-galactopyranosyl)-oleamide 

Relevant articles and documents

Synthesis and immunostimulatory activity of sugar-conjugated TLR7 ligands

Toll-like receptors (TLRs) are a type of pattern recognition receptors (PRRs), which are activated by recognizing pathogen-associated molecular patterns (PAMPs). The activation of TLRs initiates innate immune responses and subsequently leads to adaptive immune responses. TLR agonists are effective immuomodulators in vaccine adjuvants for infectious diseases and cancer immunotherapy. In exploring hydrophilic small molecules of TLR7 ligands using the cell-targeted property of a vaccine adjuvant, we conjugated 1V209, a small TLR7 ligand molecule, with various low or middle molecular weight sugar molecules that work as carriers. The sugar-conjugated 1V209 derivatives showed increased water solubility and higher immunostimulatory activity in both mouse and human cells compared to unmodified 1V209. The improved immunostimulatory potency of sugar-conjugates was attenuated by an inhibitor of endocytic process, cytochalasin D, suggesting that conjugation of sugar moieties may enhance the uptake of TLR7 ligand into the endosomal compartment. Collectively our results support that sugar-conjugated TLR7 ligands are applicable to novel drugs for cancer and vaccine therapy.

Synthesis of glycosylamines: Identification and quantification of side products

The synthesis of some glycosylamines (1-amino-1-deoxy-D-glucose, 1-amino-1-deoxy- D-galactose and 1-amino-1-deoxylactose) was carried out by treatment of the corresponding reducing sugars with ammonium hydrogencarbonate in concentrated ammonia. The reaction mixture was first analyzed by capillary electrophoresis with indirect absorbance detection and high performance anion-exchange chromatography with pulsed amperometric detection. Beside glycosylcarbamate, a known reaction by-product, fructose and lactulose were detected during the synthesis of 1-amino-1-deoxyglucose and 1-amino-1-deoxylactose, respectively. Quantification of glycosylamines was carried out by micellar electrokinetic chromatography with UV detection of their 9-fluorenylmethyloxycarbonyl (Fmoc) derivatives; lactulosylamine was thus detected in the synthesis mixture of 1-amino-1-deoxylactose. The Fmoc-glycosylamines were easily purified from the other components of the crude synthesis mixtures.