Record Information |
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Version |
1.0 |
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Update Date |
1/22/2018 12:54:54 PM |
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Metabolite ID | PAMDB120154 |
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Identification |
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Name: |
N-acetyl-β-D-glucosamine |
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Description: | An N-acetyl-D-glucosamine having β-configuration at the anomeric centre. |
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Structure |
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Synonyms: | - 2-Acetamido-2-deoxy-D-glucose
- 2-Acetylamino-2-deoxy-D-glucose
- Acetylglucosamine
- βGlcNAc
- GlcNAc-β
- N-Acetyl-beta-D-glucosamine
- N-acetyl-β-D-glucosamine
- N-Acetyl-D-glucosamine
- N-acetylglucosamine
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Chemical Formula: |
C8H15NO6 |
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Average Molecular Weight: |
221.21 |
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Monoisotopic Molecular
Weight: |
221.08994 |
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InChI Key: |
OVRNDRQMDRJTHS-FMDGEEDCSA-N |
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InChI: | InChI=1S/C8H15NO6/c1-3(11)9-5-7(13)6(12)4(2-10)15-8(5)14/h4-8,10,12-14H,2H2,1H3,(H,9,11)/t4-,5-,6-,7-,8-/m1/s1 |
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CAS
number: |
14131-68-1 |
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IUPAC Name: | 2-acetamido-2-deoxy-β-D-glucopyranose |
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Traditional IUPAC Name: |
N-acetyl-D-glucosamine |
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SMILES: | CC(=O)NC1(C(O)OC(CO)C(O)C(O)1) |
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Chemical Taxonomy |
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Taxonomy Description | This compound belongs to the class of chemical entities known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group. |
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Kingdom |
Chemical entities |
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Super Class | Organic compounds |
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Class |
Organic oxygen compounds |
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Sub Class | Organooxygen compounds |
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Direct Parent |
Acylaminosugars |
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Alternative Parents |
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Substituents |
- Acylaminosugar
- N-acyl-alpha-hexosamine
- Hexose monosaccharide
- Monosaccharide
- Oxane
- Acetamide
- Carboxamide group
- Hemiacetal
- Secondary carboxylic acid amide
- Secondary alcohol
- Carboxylic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Organic nitrogen compound
- Organopnictogen compound
- Organonitrogen compound
- Primary alcohol
- Carbonyl group
- Aliphatic heteromonocyclic compound
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Molecular Framework |
Aliphatic heteromonocyclic compounds |
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External Descriptors |
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Physical Properties |
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State: |
Solid |
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Charge: | 0 |
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Melting point: |
Not Available |
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Experimental Properties: |
Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties |
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Biological Properties |
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Cellular Locations: |
Not Available |
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Reactions: | |
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Pathways: |
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Spectra |
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Spectra: |
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References |
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References: |
- Zajonc DM, Savage PB, Bendelac A, Wilson IA, Teyton L (2008)Crystal structures of mouse CD1d-iGb3 complex and its cognate Valpha14 T cell receptor suggest a model for dual recognition of foreign and self glycolipids. Journal of molecular biology 377, Pubmed: 18295796
- Obukhova P, Rieben R, Bovin N (2007)Normal human serum contains high levels of anti-Gal alpha 1-4GlcNAc antibodies. Xenotransplantation 14, Pubmed: 17991151
- von Gunten S, Smith DF, Cummings RD, Riedel S, Miescher S, Schaub A, Hamilton RG, Bochner BS (2009)Intravenous immunoglobulin contains a broad repertoire of anticarbohydrate antibodies that is not restricted to the IgG2 subclass. The Journal of allergy and clinical immunology 123, Pubmed: 19443021
- Kuk JH, Jung WJ, Jo GH, Kim YC, Kim KY, Park RD (2005)Production of N-acetyl-beta-D-glucosamine from chitin by Aeromonas sp. GJ-18 crude enzyme. Applied microbiology and biotechnology 68, Pubmed: 15692805
- Wu D, Zajonc DM, Fujio M, Sullivan BA, Kinjo Y, Kronenberg M, Wilson IA, Wong CH (2006)Design of natural killer T cell activators: structure and function of a microbial glycosphingolipid bound to mouse CD1d. Proceedings of the National Academy of Sciences of the United States of America 103, Pubmed: 16537470
- Schneider C, Smith DF, Cummings RD, Boligan KF, Hamilton RG, Bochner BS, Miescher S, Simon HU, Pashov A, Vassilev T, von Gunten S (2015)The human IgG anti-carbohydrate repertoire exhibits a universal architecture and contains specificity for microbial attachment sites. Science translational medicine 7, Pubmed: 25568069
- Cooper DK, Good AH, Koren E, Oriol R, Malcolm AJ, Ippolito RM, Neethling FA, Ye Y, Romano E, Zuhdi N (1993)Identification of alpha-galactosyl and other carbohydrate epitopes that are bound by human anti-pig antibodies: relevance to discordant xenografting in man. Transplant immunology 1, Pubmed: 7521740
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Synthesis Reference: |
Kuk, J. H.; Jung, W. J.; Jo, G. H.; Kim, Y. C.; Kim, K. Y.; Park, R. D. Production of N-acetyl-b-D-glucosamine from chitin by Aeromonas sp. GJ-18 crude enzyme. Applied Microbiology and Biotechnology (2005), 68(3), 384-389. |
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Material Safety Data Sheet (MSDS) |
Download (PDF) |
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Links |
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External Links: |
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