N-乙酰-D-葡萄糖胺, N-Acetyl-D-glucosamine

Monosaccharide derivative of glucose found in polymers of bacterial cell walls, chitin, hyaluronic acids and various glycans. Used to identify, differentiate and characterize N-acetyl-β-D-hexoaminidase(s).

N-acetyl-D-Glucosamine (GlcNAc) is a monosaccharide derivative of glucose. It is released by the action of O-GlcNAcase, in mammalian systems from proteins that have been post-translationally modified with O-GlcNAc. Levels of O-GlcNAcylation proteins from Alzheimer’s disease brain extracts are decreased as compared to that in controls, suggesting that release of GlcNAc may contribute to pathogenesis. In E. coli, GlcNAc induces the expression of multidrug exporter genes, indicating that this sugar can alter gene expression. GlcNAc is also the monomeric unit of chitin, which is found in fungi and many invertebrates, including crustaceans, insects, and nematodes. For this reason, chemicals that inhibit the incorporation of GlcNAc into chitin are cytotoxic to these organisms.

N-Acetylglucosamine (GlcNAc), a derivative of glucose is a monosaccharide. It is a white powder and is mildly sweet. It melts at 221°C. GlcNAc is 25% soluble in water. It is present in bromelain, ricin agglutinin and abrus agglutinin, in plants. In humans, it is present in tissue plasminogen activator, growth factors and hormones.

N-Acetylglucosamine (GlcNAc) is a monosaccharide, derived from glucose and undergoes linear polymerization by (1,4)-β-linkages to form the polymer chitin. It is also a component of heterogenous polysaccharides, such as murein and hyaluronic acid. N-acetylglucosamine exhibits anti-inflammatory properties and is considered as a potential drug in the treatment of osteoarthritis. Its antiarthritic mode of mechanism involves the suppression of IL-1β (Interleuken-1β)-induced NO (nitric oxide), cyclooxygenase-2 (COX-2), and IL-6 production by inhibition of expression of iNOS (inducible nitric oxide synthase) protein and mRNA.

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.

N-Acetyl-D-glucosamine, also known as glcnac or N-acetylchitosamine, belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. N-Acetyl-D-glucosamine exists as a solid, soluble (in water), and a very weakly acidic compound (based on its pKa). N-Acetyl-D-glucosamine has been found in human prostate and intestine tissues, and has also been detected in most biofluids, including urine, breast milk, saliva, and feces. Within the cell, N-acetyl-D-glucosamine is primarily located in the cytoplasm, lysosome and myelin sheath. N-Acetyl-D-glucosamine participates in a number of enzymatic reactions. In particular, N-Acetyl-D-glucosamine can be biosynthesized from chitobiose through its interaction with the enzyme Beta-hexosaminidase subunit alpha. In addition, N-Acetyl-D-glucosamine can be converted into N-acetyl-D-glucosamine 6-phosphate; which is mediated by the enzyme N-acetyl-D-glucosamine kinase. In humans, N-acetyl-D-glucosamine is involved in the amino sugar metabolism pathway. N-Acetyl-D-glucosamine is also involved in several metabolic disorders, some of which include the salla disease/infantile sialic Acid storage disease pathway, the tay-sachs disease pathway, the g(m2)-gangliosidosis: variant b, tay-sachs disease pathway, and the sialuria or french type sialuria pathway.

N-acetyl-D-glucosamine is the D isomer of N-acetylglucosamine. It has a role as a bacterial metabolite. It is a N-acetylglucosamine and a N-acetyl-D-hexosamine.

The N-acetyl derivative of glucosamine.

Title: Glucosamine

CAS Registry Number: 3416-24-8

CAS Name: 2-Amino-2-deoxy-D-glucose

Additional Names: chitosamine

Molecular Formula: C6H13NO5

Molecular Weight: 179.17

Percent Composition: C 40.22%, H 7.31%, N 7.82%, O 44.65%

Literature References: Found in chitin, in mucoproteins, and in mucopolysaccharides. Isoln from chitin: Ledderhose, Z. Physiol. Chem. 2, 213 (1878); Hackman, Aust. J. Biol. Sci. 7, 168 (1954). Synthesis: Fischer, Leuchs, Ber. 35, 3787 (1902); 36, 24 (1903). Separation of a- and b-forms: Westphal, Holzmann, ibid. 75B, 1274 (1942). Structure: Haworth et al., J. Chem. Soc. 1939, 271; Cutler, Peat, ibid. 782; Cox, Jeffrey, Nature 143, 894 (1939). Pharmacokinetics in dog and man: I. Setnikar et al., Arzneim.-Forsch. 36, 729 (1986). Clinical trials in arthrosis: Y. Vajarudal, Clin. Ther. 3, 336 (1981); M. J. Tapadinhas et al., Pharmatherapeutica 3, 157 (1982). Review: Foster, Stacey, "The Chemistry of the 2-Amino Sugars" in C. S. Hudson et al., Advan. Carbohyd. Chem. vol. 7 (Academic Press, New York, 1952) pp 247-288. Review of pharmacology, toxicology and clinical efficacy: J. W. Anderson et al., Food Chem. Toxicol. 43, 187-201 (2005).

 Derivative Type: a-Form

CAS Registry Number: 28905-11-5

Properties: Crystals, mp 88°. [a]D20 +100° changing to +47.5° after 30 min (water).

Melting point: mp 88°

Optical Rotation: [a]D20 +100° changing to +47.5° after 30 min (water)

Derivative Type: b-Form

CAS Registry Number: 28905-10-4

Properties: Needles from methanol, dec 110°. [a]D20 +28° changing to +47.5° after 30 min (water). Very sol in water, sol in about 38 parts boiling methanol; sparingly sol in cold methanol or ethanol. Practically insol in ether, chloroform.

Optical Rotation: [a]D20 +28° changing to +47.5° after 30 min (water)

Derivative Type: N-Acetylglucosamine

CAS Registry Number: 7512-17-6

Molecular Formula: C8H15NO6

Molecular Weight: 221.21

Percent Composition: C 43.44%, H 6.83%, N 6.33%, O 43.40%

Properties: Needles from methanol + ether, mp 205°. [a]D18 +64° changing to +40.9° (in water).

Melting point: mp 205°

Optical Rotation: [a]D18 +64° changing to +40.9° (in water)

Derivative Type: Sulfate salt

CAS Registry Number: 29031-19-4

Trademarks: Dona (Rottapharm)

Line Formula: C6H13NO5.xH2SO4

Use: Pharmaceutic aid.

Therap-Cat: Antiarthritic.

Keywords: Antiarthritic/Antirheumatic.

Product name: 2-Acetamido-2-deoxy-D-glucose; N-Acetyl-D-glucosamine

CAS: 7512-17-6                    M.F.: C₈H₁₅NO₆               M.W.: 221.21

References:

1. Berkin A, Szarek WA, Kisilevsky R, Glycoconjugate J. 2005, 22, p443
2. Blach WE, Dunphy WG, Braell WA, et al., Cell 1984, p405
3. Armstrong C, Schubert J, Ueda E, et al., J. Biol. Chem. 1992, 267, 35, p25347