3646-68-2

Usage

Uses

Used in Pharmaceutical Industry:
D-Glucosaminic acid is used as a starting material for the synthesis of aldonic acids, which are important in the development of various pharmaceutical compounds. These aldonic acids, containing a free carboxyl group and all hydroxyl functions esterified with a simple carboxylic acid, are well-established derivatives that can be utilized in the creation of new drugs and therapeutic agents.
Used in Biochemical Research:
D-Glucosaminic acid serves as a valuable compound in biochemical research, particularly in the study of glycobiology and the role of amino sugars in various biological processes. Its unique structure allows researchers to explore its interactions with other biomolecules and its potential applications in the development of novel therapeutic strategies.
Used in Nutritional Supplements:
D-Glucosaminic acid is also used in the formulation of nutritional supplements, particularly those aimed at supporting joint health and reducing the symptoms of osteoarthritis. Its role in the synthesis of proteoglycans and its potential anti-inflammatory effects make it a popular ingredient in health products designed to improve joint function and reduce discomfort.

InChI:InChI=1/C6H13NO6/c7-3(6(12)13)5(11)4(10)2(9)1-8/h2-5,8-11H,1,7H2,(H,12,13)

Upstream product

• 74-90-8 hydrogen cyanide 
• 1114-34-7 D-lyxose 
• 50-69-1 D-ribose 
• 66-84-2 D-(+)-glucosamine hydrochloride 
• 14257-69-3 glucosamine 
• 90-76-6 2-deoxy-2-amino glucose 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 108-24-7 acetic anhydride 
• 3416-24-8 2-amino-2-deoxyglucose 
• 7732-18-5 water 
• 83078-98-2 ethyl 2-amino-4,6-O-benzylidene-2-deoxy-D-gluconate 
• 71389-27-0 2-amino-2-deoxy-altronic acid-4-lactone 
• 90-76-6 galactosamine 

Downstream Products

• 10326-41-7 D-Lactic acid 
• 110-15-6 succinic acid 
• 144-62-7 oxalic acid 
• 64-19-7 acetic acid 
• 5469-77-2 2-acetamido-2-deoxy-D-glucono-1,4-lactone 
• 40149-90-4 4,6-O-benzylideneglucosaminic acid ethyl ester hydrochloride 
• 126778-04-9 2-benzamido-4,6-di-O-benzoyl-2,3-dideoxy-D-erythro-hex-2-enono-1,5-lactone 
• 126778-05-0 2-benzamido-5,6-di-O-benzoyl-2,3-dideoxy-D-erythro-hex-2-enono-1,4-lactone 
• 133473-14-0 methyl 2-<(9-phenylfluoren-9-yl)amino>-2-deoxy-3,4:5,6-di-O-isopropylidene-D-gluconate 
• 10323-20-3 D-Arabinose 
• 583-50-6 D-erythrose 
• 3416-24-8 2-amino-2-deoxyglucose 
• 53684-93-8 2-acetamido-4,6-O-benzylidene-2,3-dideoxy-D-erythro-hex-2-enono-1,5-lactone 

Relevant academic research and scientific papers

Catalytic synthesis of D-glucosaminic acid from D-glucosamine on active charcoal-supported Pd-Bi catalysts

D-Glucosaminic acid (2-amino-2-deoxy-D-gluconic acid), is a component of bacterial lipopolysaccharides, sweetener, condiments, and a chiral synthon. A catalytic oxidation of D-glucosamine to D-glucosaminic acid by molecular oxygen on active charcoal-supported Pd-Bi catalysts is described in good yield. Copyright Taylor & Francis Group, LLC.

D - production of glucosamine acid or its analogs, as well as catalyst composition

PROBLEM TO BE SOLVED: To provide a means for simply and efficiently producing D-glucosamic acid or its analogue.SOLUTION: By using a catalyst composition including a carrier comprising hydrotalcite, magnesium oxide or calcium oxide and gold particles carried on the carrier, it becomes possible to produce D-glucosamic acid or its analogue simply and efficiently from corresponding D-glucosamine or its analogue.

Characterization of d-amino acid aminotransferase from Lactobacillus salivarius

We searched a UniProt database of lactic acid bacteria in an effort to identify d-amino acid metabolizing enzymes other than alanine racemase. We found a d-amino acid aminotransferase (d-AAT) homologous gene (UniProt ID: Q1WRM6) in the genome of Lactobacillus salivarius. The gene was then expressed in Escherichia coli, and its product exhibited transaminase activity between d-alanine and α-ketoglutarate. This is the first characterization of a d-AAT from a lactic acid bacterium. L. salivarius d-AAT is a homodimer that uses pyridoxal-5′-phosphate (PLP) as a cofactor; it contains 0.91 molecules of PLP per subunit. Maximum activity was seen at a temperature of 60 °C and a pH of 6.0. However, the enzyme lost no activity when incubated for 30 min at 30 °C and pH 5.5 to 9.5, and retained half its activity when incubated at pH 4.5 or 11.0 under the same conditions. Double reciprocal plots of the initial velocity and d-alanine concentrations in the presence of several fixed concentrations of α-ketoglutarate gave a series of parallel lines, which is consistent with a Ping-Pong mechanism. The Km values for d-alanine and α-ketoglutarate were 1.05 and 3.78 mM, respectively. With this enzyme, d-allo-isoleucine exhibited greater relative activity than d-alanine as the amino donor, while α-ketobutylate, glyoxylate and indole-3-pyruvate were all more preferable amino acceptors than α-ketoglutarate. The substrate specificity of L. salivarius d-AAT thus differs greatly from those of the other d-AATs so far reported.

Enzymatic synthesis of aldonic acids

Several aldonic acids (d-mannonic, d-galactonic, d-xylonic, 2-deoxy-d-arabinohexonic (2-deoxy-d-gluconic)) were prepared on a scale of several grams by a simple oxidation catalyzed by glucose oxidase in pure water.

Reactivities of some aldoses and aldosamines towards potassium bromate in hydrochloric acid medium

The kinetics of oxidation of some aldoses and aminosugars by potassium bromate in hydrochloric acid medium have been studied. The reactions appear to proceed through the intermediate formation of bromate esters followed by the decomposition of the esters to give products. Hydrogen-ion accelerates tide rate of each reaction. The thermodynamic values associated with the equilibrium stage and the activation parameters associated with the rate- determining step have been computed.

The reaction of hyaluronic acid and its monomers, glucuronic acid and N- acetylglucosamine, with reactive oxygen species

Synovial fluid is a ~0.15% (w/v) aqueous solution of hyaluronic acid (HA), a polysaccharide consisting of alternating units of GlcA and GlcNAc. In synovial fluid of patients suffering from rheumatoid arthritis, HA is thought to be degraded either by radicals generated by Fenton chemistry (Fe2+/H2O2) or by NaOCl generated by myeloperoxidase. We investigated the course of model reactions of these two reactants in physiological buffer with HA, and with the corresponding monomers GlcA and GlcNAc. meso-Tartaric acid, arabinuronic acid, arabinaric acid and glucaric acid were identified by GC-MS as oxidation products of glucuronic acid. When GlcNAc was oxidised, erythronic acid, arabinonic acid, 2-acetamido-2-deoxy-gluconic acid, glyceric acid, erythrose and arabinose were formed. NaOCl oxidation of HA yielded meso-tartaric acid; in addition, arabinaric acid and glucaric acid were obtained by oxidation with Fe2+/H2O2. These results indicate that oxidative degradation of HA proceeds primarily at glucuronic acid residues. meso-Tartaric acid may be a useful biomarker of hyaluronate oxidation since it is produced by both NaOCl and Fenton chemistry.

Kinetics and mechanism of the oxidation of some aldoses, amino sugars and methylated sugars by tris(pyridine-2-carboxylato)manganese(III) in weakly acidic medium

The kinetics of oxidation of some aldoses, amino sugars and methylated sugars by tris(pyridine-2-carboxylato)manganese(III) have been studied spectrophotometrically in sodium picolinate -picolinic acid buffer medium. The reactions are first order with respect to both manganese(III) and sugar concentrations, but independent with respect to sodium picolinate - picolinic acid buffer medium. The mechanism for the reactions is discussed.

Reactivities of osmium (VIII) towards some aldoses, amino sugars, and methylated sugars in alkaline medium

The kinetics of oxidation of some aldoses, amino sugars and methylated sugars by osmium (VIII) have been studied spectrophotometrically in alkaline medium. The reactions are first-order with respect to both [sugar]≤9.0×10-3 mol dm-3 and [OH-]≤10.0×10-2 mol dm-3 but tends toward zero order with respect to each at higher concentration. Activation parameters of the reactions have been calculated and plausible reaction mechanisms have been suggested.

Sodium N-Chlorobenzenesulfonamide as a Selective Oxidant for Hexosamines in Alkaline Medium: A Kinetic and Mechanistic Study

Oxidation of D-mannosamine (1), D-glucosamine (2), and D-galctosamine (3) by sodium N-chlorobenzenesulfonamide or chloramine-B (CAB) at 313 K is followed by a shortening of carbon chain and obeys the rate law, rate = k[CAB][sugar][HO-]x, where x is less than unity. The products are arabinonic acid, ribonic acid, and erythronic acid for 1 and 2 with smaller amounts of glyceric and hexonic acids, while lyxonic and threonic acids are predominant in the oxidation of 3 with smaller amounts of glyceric and hexonic acids. Proton inventory studies made in a H2)O-D2)O mixture point toward a single transition state. In the proposed mechanism the alkoxy anion (S-) of the hexosamine formed in a base-catalyzed reaction at C-1 carbon is subjected to an electrophilic rate-limiting attack by Cl+ of the oxidant. The hexonic acid formed is decarboxylated with loss of ammonia to form the respective pentose, which is further converted into the corresponding pentonic acid. The breaking of the bond between C-1 and C-2 carbons in pentose yields tetronic acids. The thermodynamic parameters for sugar alkoxy anion formation and activation parameters for the rate-limiting step have been evaluated.

Kinetic behaviour and relative reactivities of some aldoses, amino sugars, and methylated sugars towards platinum(IV) in alkaline medium

The kinetic behaviour and relative reactivities of some carbohydrates (aldoses, amino sugars and methylated sugars) towards platinum(IV) in alkaline medium have been investigated. The reactions are first order with respect to [substrate] and PtIV. The rates increase with the increase in OH-. The reactions show pseudo-first-order dependence on OH-. The oxidation rates in alkaline medium follow the order triose>tetrose>pentose>hexose. Activation parameters of the reactions have been calculated. Mechanisms have been proposed for the reactions. Copyright (C) 1998 Elsevier Science Ltd.