14196-86-2

Basic information

• Product Name: β-galactosylamine
• Synonyms: β-galactosylamine
• CAS NO: 14196-86-2
• Molecular Weight: 179.173
• Mol File: 14196-86-2.mol

Chemical Properties

• CAS DataBase Reference: β-galactosylamine(CAS DataBase Reference)
• NIST Chemistry Reference: β-galactosylamine(14196-86-2)
• EPA Substance Registry System: β-galactosylamine(14196-86-2)

Safety Data

• Hazardous Substances Data: 14196-86-2(Hazardous Substances Data)

Upstream product

• 2776-93-4 2-acetamido-1-N-(L-β-aspartyl)-2-deoxy-β-D-glucopyranosylamine 
• 16405-05-3 2-acetamido-1-N-(1-benzyloxy-N-benzyloxycarbonyl-4-L-aspartyl)-2-deoxy-β-D-glucopyranosylamine 
• 91032-39-2 C₆₆H₅₈Cl₂N₈O₂₃ 
• 7284-16-4 p-nitrophenyl 2-acetamido-2-deoxy-β-D-glucopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranoside 
• 9005-49-6 heparin 
• 9050-30-0 heparan sulfate 
• 24967-93-9 chondroitin sulfate 
• 24967-94-0 dermatan sulfate 
• 9004-61-9 hyaluronic acid 
• 1772-03-8 D-(+)-galactosamine hydrochloride 
• 1415305-18-8 4,6-dimethoxy-1,3,5-triazin-2-yl β-D-galactosamine hydrochloride 
• 57-48-7 D-Fructose 
• 1415305-17-7 4,6-dimethoxy-1,3,5-triazin-2-yl β-D-glucosamine hydrochloride 
• 29886-32-6 β-D-GlcpNAc(1->4)-D-GlcNAc-ol 

Downstream Products

• 6857-22-3 N-(2,4,5-trihydroxy-6-hydroxymethyl-tetrahydropyran-3-yl)butyramide 
• 68742-89-2 2-<3-(2-Chlor-ethyl)-ureido>-2-deoxy-D-glucopyranose 
• 111286-55-6 2-deoxy-2-<(4,4-dimethyl-2,6-dioxocyclohexylidenemethyl)amino>-α,β-D-glucopyranose 
• 70866-07-8 N₁-(2-chloroethyl)-N₃-glucosamino-N₁-nitrosourea 
• 41107-82-8 2,5-anhydro-D-mannitol 
• 3006-60-8 2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate 
• 13996-68-4 2-(3-benzoylthioureido)-2-deoxy-D-glucopyranose 
• 6857-21-2 N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]propanamide 
• 3006-60-8 Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-4-yl ester 
• 31505-45-0 2-deoxy-2-phthalimido-D-glucopyranose 
• 14307-03-0 2-amino-2-deoxy-D-glucitol 
• 3646-68-2 D-glucosaminic acid 
• 75-47-8 iodoform 
• 17460-13-8 2-(D-arabino-1',2',3',4'-tetrahydroxybutyl)-5-(D-erythro-2,3,4-trihydroxybutyl)piperazine 

Relevant articles and documents

Acidolysis-based component mapping of glycosaminoglycans by reversed-phase high-performance liquid chromatography with off-line electrospray ionization-tandem mass spectrometry: Evidence and tags to distinguish different glycosaminoglycans

Diverse monosaccharide analysis methods have been established for a long time, but few methods are available for a complete monosaccharide analysis of glycosaminoglycans (GAGs) and certain acidolysis- resistant components derived from GAGs. In this report, a reversed-phase high-performance liquid chromatography (RP-HPLC) method with pre-column 1-phenyl-3-methyl-5-pyrazolone (PMP) derivatization was established for a complete monosaccharide analysis of GAGs. Good separation of glucosamine/ mannosamine (GlcN/ManN) and glucuronic acid/iduronic acid (GlcA/IdoA) was achieved. This method can also be applied to analyze the acidolysis-resistant disaccharides derived from GAGs, and the sequences of these disaccharides were confirmed by electrospray ionization-collision-induced dissociation- tandem mass spectrometry (ESI-CID-MS/MS). These unique disaccharides could be used as markers to distinguish heparin/heparan sulfate (HP/HS), chondroitin sulfate/dermatan sulfate (CS/DS), and hyaluronic acid (HA).

CHONDROITIN COMPLEXES FOR TRANSCUTANEOUS ABSORPTION

The present invention relates to the use of chondroitin as a transdermal carrier and slow-release system for active ingredients in pharmaceutical and cosmeceutical compositions.

Anti-hepatitis b virus norbisabolane sesquiterpenoids from phyllanthus acidus and the establishment of their absolute configurations using theoretical calculations

Nineteen new highly oxygenated norbisabolane sesquiterpenoids, phyllanthacidoid acid methyl ester (1), and C-T (4-21), were isolated from Phyllanthus acidus Skeels, together with two known ones, phyllanthusols A (2) and B (3), whose sugar moiety was revised as glucosamine-N-acetate, rather than the previously assigned mannosamine-N-acetate. Compounds 2 and 3 were renamed respectively as phyllanthacidoids A (2) and B (3) to avoid confusion. All of the isolates except for 1 are glycosides, whose saccharide moieties possess a pentaoxy cyclohexane (scyllo quercitol) connecting with glucosamine-N-acetate or glucosyl moieties, which are first examples in natural products. Phyllanthacidoids N-R (15-19) with 8R configurations and/or 5,8-diketal skeleton, are unprecedented structures among norbisabolane sesquiterpenoids. Phyllanthacidoids S (20) and T (21) have the unusual tricyclo [3.1.1.1] oxygen bridge skeleton formed by a diketal system, of which the relative configurations of the aliphatic chain were assigned on the basis of heteronuclear coupling constants. The absolute configurations of compounds (1-21) were established by means of calculated electronic circular dichroism (ECD) and coupling constants. Compounds 1-5, 7-9, 10, and 14 displayed potential anti-hepatitis B virus (HBV) activities, with IC50 values of 0.8-36 μM against HBV surface antigen (HBsAg) and HBV excreted antigen (HBeAg), and the results indicated that the 5-ketal group and sugar moieties had contributions to the selectivity of HBsAg and HBeAg.

Structural characterization of the core oligosaccharide isolated from the lipopolysaccharide of the psychrophilic bacterium Colwellia psychrerythraea strain 34H

Cold-adapted bacteria are microorganisms that thrive at very low temperatures in permanently cold environments (0-10 °C). Their ability to survive under these harsh conditions is the result of molecular evolution and adaptations, which include the structural modification of the phospholipid membrane. To give insight into the role of the membrane in the mechanisms of adaptation to low temperature, the characterization of other cell-wall components is necessary. Among these components, the lipopolysaccharides are complex amphiphilic macromolecules embedded in the outer leaflet of the external membrane, of which they are the major constituents. The cold-adapted Colwellia psychrerythraea 34H bacterium, living in deep sea and Arctic and Antarctic sea ice, was cultivated at 4 °C. The lipooligosaccharide (LOS) was isolated and analysed by means of chemical analysis. Then it was degraded either by mild hydrazinolysis (O-deacylation) or hot KOH (4 M; N-deacylation). Both products were investigated in detail by 1H and 13C NMR spectroscopy and by ESI FT-ICR mass spectrometry. The oligosaccharide portion consists of a unique and very short species with the following general structure: α-L-Col-(1→2)-α-D-GalA-(1→2)-α-D-Man-[3-P-D-Gro] -(1→5)-α-D-Kdo-4-P-Lipid-A. The structural characterization of the lipooligosaccharide from the steno-psychrophilic bacterium Colwellia psychrerythraea strain 34H has been achieved by means of chemical analysis, mass spectrometry, and NMR spectroscopy experiments. The data revealed a very short, negatively charged, and unique oligosaccharide, lacking heptose residues. Copyright

4,6-dimethoxy-1,3,5-triazin-2-yl-d-glycosaminides: Novel substrates for transglycosylation reaction catalyzed by exo-d-glucosaminidase from amycolatopsis orientalis

A novel sugar adduct, 4,6-dimethoxy-1,3,5-triazin-2-yl-d-glucosaminide (GlcN-DMT), has been prepared by the reaction of d-glucosamine (GlcN) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-morpholinium chloride (DMT-MM). The adduct was recognized by exo-d-glucosaminidase (GlcNase) from Amycolatopsis orientalis and transferred the GlcN moiety, giving rise to the corresponding glucosaminides. This chemo-enzymatic process was successfully applied to d-galactosamine (GalN). GalN-DMT prepared directly from GalN and DMT-MM behaved as an efficient glycosyl donor for transfer of the GalN moiety catalyzed by the same enzyme. The introduction of the 4,6-dimethoxy-1,3,5-triazin-2-yl leaving group to the anomeric center significantly enhanced transglycosylating ability, resulting in the efficient glycosidase-catalyzed synthesis of glycosaminides.

HYBRID COMPOUNDS BASED ON POLYOL(S) AND AT LEAST ONE OTHER MOLECULAR ENTITY, POLYMERIC OR NON-POLYMERIC, IN PARTICULAR OF THE POLYORGANOSILOXANE TYPE, PROCESS FOR THE PREPARATION THEREOF, AND APPLICATIONS THEREOF

The invention relates to novel hybrid compounds comprising at least one polyon entity (Po)—for example oligomer or polymer—in which at least one of the hydroxyl functions of Po is substituted by at least one entity A that can be of a variable nature, for example polymer (e.g. polyorganosiloxane-POS), hydrocarbonated or mineral. The bond Ro between the entity Po and the entity A is obtained by means of “click chemistry” and corresponds to formula (II.1) or (II.2), Z representing —CH— or —N—. A is an entity selected from the group comprising the various polyols of Po, polyorganosiloxanes (POS), polyalkylene glycols, polyamides, polyesters, polystyrenes, alkyls, alkenyls, alkynyls, aryls, and combinations thereof, in addition to mineral materials such as silica and the combinations thereof. Said hybrid components can be used as emulsifiers, especially for cosmetics.

Substrate specificity of N-acetylhexosamine kinase towards N-acetylgalactosamine derivatives

We report herein a bacterial N-acetylhexosamine kinase, NahK, with broad substrate specificity towards structurally modified GalNAc analogues, and the production of a GalNAc-1-phosphate library using this kinase.

Preparation of glucosamine

Disclosed is a process for the preparation of a glucosamine acid addition salt from fructose and ammonia or an ammonia source such as an ammonium compound by contacting fructose and ammonia or an ammonia source in the presence of (i) a solvent comprising about 25 to 100 weight percent water and 75 to 0 weight percent of an inert, organic, water-miscible solvent at a WWpH or SWpH of about 1 to 6; or (ii) a solvent comprising about 75 to 100 weight percent of an inert, organic, water-miscible solvent and 0 to 25 weight percent water at a WWpH or SWpH of about 1 to 10. A mannosamine acid addition salt also is produced as a co-product of the process.

Enhanced enzymatic hydrolysis of langostino shell chitin with mixtures of enzymes from bacterial and fungal sources

A combination of enzyme preparations from Trichoderma atroviride and Serratia marcescens was able to completely degrade high concentrations (100 g/L) of chitin from langostino crab shells to N-acetylglucosamine (78%), glucosamine (2%), and chitobiose (10%). The result was achieved at 32°C in 12 days with no pre-treatment (size reduction or swelling) of the substrate and without removal of the inhibitory end-products from the mixture. Enzymatic degradation of three forms of chitin by Serratia/Trichoderma and Streptomyces/Trichoderma blends was carried out according to a simplex-lattice mixture design. Fitted polynomial models indicated that there was synergy between prokaryotic and fungal enzymes for both hydrolysis of crab chitin and reduction of turbidity of colloidal chitin (primarily endo-type activity). Prokaryotic/fungal enzymes were not synergistic in degrading chitosan. Enzymes from prokaryotic sources had much lower activity against chitosan than enzymes from T. atroviride.

Selective N-deacetylation of p-nitrophenyl N,N'-diacetyl-β-chitobioside and its use to differentiate the action of two types of chitinases

We report the synthesis of a novel compound for chitinase assays, p-nitrophenyl 2-acetamido-4-O-(2-amino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranoside [GlcNGlcNAc-pNP] by selective N-deacetylation of p-nitrophenyl 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranoside [(GlcNAc)2-pNP] using a purified chitin deacetylase isolated from Colletotrichum lindemuthianum ATCC 56676. FABMS, 1H NMR, and 13C NMR analyses confirmed the structure of this new compound. This disaccharide derivative can be used to distinguish special chitinases that effectively remove partially deacetylated parts of substrates within a mixture of chitinases which degrades (GlcNAc)2-pNP. Copyright (C) 1999 Elsevier Science Ltd.