50444-86-5

Usage

Amino sugar derivative

1-Amino-1-deoxy-beta-D-galactose is a compound belonging to the family of aminosugars, which are sugars that have an amine group attached to them.

Derivative of galactose

It is a derivative of galactose, which is a simple sugar commonly found in milk and dairy products.

Used in carbohydrate synthesis

It is commonly used in the synthesis of various carbohydrates and glycoconjugates, which are molecules composed of carbohydrates and other substances such as lipids or proteins.

Potential pharmaceutical applications

1-Amino-1-deoxy-beta-D-galactose has potential applications in the development of pharmaceuticals, particularly in the design and synthesis of glycosylated drugs.

Role in glycan-protein interactions

It is utilized in the study of glycan-protein interactions, which are important in many biological processes.

Therapeutic potential

It has been investigated for its potential as a therapeutic agent for conditions such as diabetes and cancer.

Significant role in carbohydrate chemistry

1-Amino-1-deoxy-beta-D-galactose plays a significant role in the field of carbohydrate chemistry and has important implications for drug discovery and development.

Upstream product

• 492-61-5 β-D-glucose 
• 41355-50-4 2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine 
• 20379-59-3 D-glucopyranosyl azide 
• 2280-44-6 D-Glucose 
• 849367-23-3 (3aS,5R,6S,7S,7aR)-5-Hydroxymethyl-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d]oxazole-6,7-diol 
• 10257-28-0 D-Galactose 
• 35899-89-9 1-amido-1-deoxygalactopyranose 
• 67-56-1 methanol 
• 59-23-4 D-Galactose 
• 7664-41-7 ammonia 
• 530-26-7 D-Mannose 
• 51970-29-7 α-D-mannopyranosyl azide 
• 53784-29-5 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl azide 
• 5505-63-5 D-mannosamine hydrochloride 

Downstream Products

• 6983-36-4 N-acetyl-β-D-glucopyranosylamine 
• 33758-19-9 N-bromoacetyl-β-D-glucopyranosylamine 
• 136860-06-5 N--L-phenylalanyl-L-leucyl>-β-D-glucopyranosylamine 
• 73847-68-4 β-D-glucopyranosyl-p-nitrophenyltriazene 
• 18918-51-9 N-(1-β-D-Glucopyranosyl)-4-nitro-benzamid 
• 50802-49-8 β-D-glucopyranosyl isothiocyanate 
• 41355-50-4 2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine 
• 58484-07-4 1-(2-chloroethyl)-3-(β-D-glucopyranosyl)-1-nitrosourea 
• 33758-19-9 N-bromoacetyl-β-D-galactopyranosylamine 
• 83306-52-9 N¹-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)succinamic acid 
• 33758-19-9 N-bromoacetyl-β-D-mannopyranosylamine 
• 67283-56-1 N-ε-aminocaproyl-β-D-mannopyranosylamine 
• 287173-96-0 (S)-2-(9H-Fluoren-9-ylmethoxycarbonylamino)-N-((2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-succinamic acid pentafluorophenyl ester 

Relevant academic research and scientific papers

Preparation and evaluation of a molecular recognition bionic solid phase extraction column for separation of glucosides

Amolecular recognition bionic solid phase extraction (SPE) column for separation of glucosides has been prepared using a positively charged β-glucosylamidine as the ligand inwhich a glyconmoiety is connected via an N-glycoside linkage. β-Glucosylamidine, highly potent and selective inhibitors of β-glycosidase, is immobilized through a one-step synthesize procedure involving the addition of β-glucosylamine and 2-iminothiolane. HCl simultaneously to a matrix modified with maleimido groups via an appropriate spacer to give a molecular recognition absorbent for β-glucosides. N-octyl-β-D-glucopyranoside and β-D-galactopyranoside or α-D-mannopyranoside was directly chromatographed through the bionic chromatographic column, resulting in a much stronger retention of β-D-glucopyranoside than β-D-galactopyranoside and α-D-mannopyranoside. The retained glucopyranoside could only be eluted by glucose solution. This indicates that the binding of the glucoside was of specific nature that corresponds to the glycon substrate specificity of the glucoside. The ease of preparation and the selective nature of the molecular recognition bionic chromatography should promise a large-scale preparation of the molecular recognition adsorbent for the purification and removal of glucosides according to their glycon substrate specificity.

Cobalt(III) Complexes of D -Galactosylamine

The β-pyranose isomer of D-galactosylamine (1) formed complexes with three different cobalt(III) fragments. Crystals containing the dication [Co(tren)(β-D-Galp1N2H-1-κ2N1,O2)]2+ (3) showed coordination through the anomeric amino group (N1) and the deprotonated hydroxy group (O2) of the 4C1 β-pyranose form, which is also the major isomer of free galactosylamine. The cationic complexes [Co(fac-dien)(β-D-Galp1N2H-1-κ2N1,O2)]2+ (4) and [Co(phen)2(β-D-Galp1N2H-1-κ2N1,O2)]2+ (5) were analysed by NMR spectroscopy and showed the same coordination mode as 3. In terms of available ligand isomers it was shown that 1 exhibits an anomeric equilibrium in solution of both pyranose and both furanose forms as is typical for the parent glycose, galactose.

Improved synthesis of glycosylamines and a straightforward preparation of N-acylglycosylamines as carbohydrate-based detergents

D-Glucose, D-galactose, lactose, cellobiose, and maltose yield quantitatively the corresponding glycosylamine when treated at 42 deg C for 36 h with a commercial aqueous aolution of ammonia in the presence of one equivalent of ammonium hydrogen carbonate.After lyophilisation, the residue (i.e., the pure glucosylamine) was dissolved in a mixture of ethanol and water, and treated with acyl chlorides to afford in a few minutes N-acylglucosylamines.Micellar proporties of these amophiphilic derivatives were determined.Keywords: Glycosylamines; N-Acylglycosylamines; Non-ionic detergents; Carbohydrate-based detergents; Surfactants

Carbohydrate-based switch-on molecular sensor for Cu(II) in buffer: Absorption and fluorescence study of the selective recognition of Cu(II) ions by galactosyl derivatives in HEPES buffer

1-(β-D-Galactopyranosyl-1′-deoxy-1′-iminomethyl) -2-hydroxynaphthalene (L1), possessing an ONO binding core, was found to be selective for Cu2+ ions in N-[2-hydroxyethyl]piperazine- N′-[2-ethanesulfonic acid] buffer, at concentrations ≤580 ppb, at physiological pH by eliciting switch-on behavior, whereas the other ions, viz., Mg2+, Ca2+, Mn2+, Fe2+, Co 2+, Ni2+, Zn2+, and Cd2+, caused no significant change in the fluorescence. Whereas the binding characteristics were ascertained by absorption spectroscopy, the species formed were shown by Q-TOF ES MS.

Experimental and computational studies of the recognition of amino acids by galactosyl-imine and -amine derivatives: An attempt to understand the lectin-carbohydrate interactions

(Chemical Equation Presented) A galactosyl-naphthyl-imine-based derivative, 1-(β-D-galactopyranosyl-1′-deoxy-1′-iminomethyl)-2- hydroxynaphthalene (GNI), and a galactosyl-naphthyl-amine-based derivative, 1-(galactopyranosyl-1′-deoxy-1′-aminomethyl)-2-hydroxynaphthalene (GNA), possessing an ONO binding core were studied for their recognition of naturally occurring amino acids using fluorescence and absorption spectroscopy, and the corresponding association constants were derived for the complexes formed. The complexes formed between GNI/GNA and amino acids were supported by electrospray ionization mass spectrometry (ESI/MS). The structures of the complexes were optimized by computational studies using density functional theory, and stabilization energies were computed for the complexes to substantiate the interactions present between GNI/GNA and amino acid. The interactions were found to be primarily hydrogen bonding in nature. These interactions are reminiscent of those present in the lectin-carbohydrate and glycosidase substrate. Thus, the carbohydrate moiety present in GNI shows high specificity toward the -COOH group of the amino acid, which may be relevant to such interactions present between the carbohydrates and the polypeptides.

Synthesis of β-D-glucopyranuronosylamine in aqueous solution: Kinetic study and synthetic potential

A systematic study of the synthesis of β-D-glucopyranuronosylamine in water is reported. When sodium d-glucuronate was reacted with ammonia and/or volatile ammonium salts in water a mixture of β-D-glucopyranuronosylamine and ammonium N-β-D-glucopyranuronosyl carbamate was obtained at a rate that strongly depended on the experimental conditions. In general higher ammonia and/or ammonium salt concentrations led to a faster conversion of the starting sugar into intermediate species and of the latter into the final products. Yet, some interesting trends and exceptions were observed. The use of saturated ammonium carbamate led to the fastest rates and the highest final yields of β-D-glucopyranuronosylamine/carbamate. With the exception of 1 M ammonia and 0.6 M ammonium salt, after 24 h of reaction all tested protocols led to higher yields of β-glycosylamine/carbamate than concentrated commercial ammonia alone. The mole fraction of α-D-glucopyranuronosylamine/carbamate at equilibrium was found to be 7-8% in water at 30 °C. Concerning bis(β-D-glucopyranuronosyl)amine, less than 3% of it is formed in all cases, with a minimum value of 0.5% in the case of saturated ammonium carbamate. Surprisingly, the reaction was consistently faster in the case of sodium d-glucuronate than in the case of D-glucose (4-8 times faster). Finally, the synthetic usefulness of our approach was demonstrated by the synthesis of three N-acyl-β-D-glucopyranuronosylamines and one N-alkylcarbamoyl-β-D- glucopyranuronosylamine directly in aqueous-organic solution without resorting to protective group chemistry.

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.

7-nitrobenzo-2-oxa-1, 3-diazole deoxyglucosamine as well as preparation method and application of 7-nitrobenzo-2-oxa-1, 3-diazole deoxyglucosamine

The invention discloses following three 7-nitrobenzo-2-oxa-1, 3-diazole (NBD) deoxyglucosamine (NBDG) compounds as well as pharmaceutically acceptable salts, a preparation method and an application thereof. The key point of the invention is that the following compounds are deoxyglucose analogues with fluorescein, are used for monitoring glucose uptake of living cell tissues, are one of indexes forjudging cell viability, are used for monitoring local tumor formation, and can also be used as high-sensitivity fluorescent markers in a glucose transport detection method.

The effect of monosaccharides on self-assembly of benzenetricarboxamides

The interaction between monosaccharides exhibits an important role in the assembly of monosaccharide-containing molecules. In this work, three common monosaccharides, glucose, galactose and mannose, are employed to investigate the effect of monosaccharide on the self-assembly of benzenetricarboxamide (BTA) core-containing molecules. In the presence of monosaccharides, three benzenetricarboxamide derivatives aggregate into different ordered structures. When alanine linkers are introduced to these molecules between the core and the monosacchride, morphologies of three types of monosaccharide BTAs turned to disordered, meanwhile their structures become similar with the increase of the length of alanine linkers, indicating the disappearance of the monosaccharide effects.

Development of photoswitchable inhibitors for β-galactosidase

Azobenzenes are of particular interest as a photochromic scaffold for biological applications because of their high fatigue resistance, their large geometrical change between extended (trans) and bent (cis) isomer, and their diverse synthetic accessibility. Despite their wide-spread use, there is no reported photochromic inhibitor of the well-investigated enzyme β-galactosidase, which plays an important role for biochemistry and single molecule studies. Herein, we report the synthesis of photochromic competitive β-galactosidase inhibitors based on the molecular structure of 2-phenylethyl β-d-thiogalactoside (PETG) and 1-amino-1-deoxy-β-d-galactose (β-d-galactosylamine). The thermally highly stable PETG-based azobenzenes show excellent photochromic properties in polar solvents and moderate to high photostationary states (PSS). The optimized compound 37 is a strong competitive inhibitior of β-galactosidase from Escherichia coli and its inhibition constant (Ki) changes between 60 nM and 290 nM upon irradiation with light. Additional docking experiments supported the observed structure-activity relationship.