アセチルグルコサミン
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- N-acetyl-D-glucosamine
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/01/05 20:34:11」(JST)
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| N-Acetylglucosamine |
|
IUPAC name
2-(Acetylamino)-2-deoxy-D-glucose
|
Other names
N-Acetyl-D-Glucosamine
GlcNAc
NAG
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| Identifiers |
| CAS number |
7512-17-6 Y |
| PubChem |
24139 |
| ChemSpider |
22563 Y |
| UNII |
V956696549 N |
| ChEBI |
CHEBI:28009 N |
| ChEMBL |
CHEMBL447878 Y |
| Jmol-3D images |
Image 1 |
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O=C(N[C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@H]1O)CO)C
|
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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 Y
Key: OVRNDRQMDRJTHS-FMDGEEDCSA-N Y
InChI=1/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
Key: OVRNDRQMDRJTHS-FMDGEEDCBL
|
| Properties |
| Molecular formula |
C8H15NO6 |
| Molar mass |
221.21 |
| Melting point |
211 |
| Hazards |
| S-phrases |
S24/25 |
| Related compounds |
| Related Monosaccharides |
N-Acetylgalactosamine |
| Related compounds |
Glucosamine
Glucose |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) |
| N (verify) (what is: Y/N?) |
| Infobox references |
|
|
N-Acetylglucosamine (N-acetyl-D-glucosamine, or GlcNAc, or NAG) is a monosaccharide derivative of glucose. It is an amide between glucosamine and acetic acid. It has a molecular formula of C8H15NO6, a molar mass of 221.21 g/mol, and it is significant in several biological systems.
It is part of a biopolymer in the bacterial cell wall, built from alternating units of GlcNAc and N-acetylmuramic acid (MurNAc), cross-linked with oligopeptides at the lactic acid residue of MurNAc. This layered structure is called peptidoglycan (formerly called murein).
GlcNAc is the monomeric unit of the polymer chitin, which forms the outer coverings of insects and crustaceans. It is the main component of the radulas of mollusks, the beaks of cephalopods, and a major component of the cell walls of most Fungi.
Polymerized with glucuronic acid, it forms hyaluronan.
GlcNAc has been reported to be an inhibitor of elastase release from human polymorphonulear leukocytes (range 8 - 17% inhibition), however this is much weaker than the inhibition seen with N-acetyl-galactosamine (range 92 - 100%).[1]
Contents
- 1 Medical uses
- 2 See also
- 3 References
- 4 External links
Medical uses
It has been proposed as a treatment for autoimmune diseases,[2] and recent tests have claimed some success.[3]
See also
- Keratan sulfate
- Chitin
- N-acetyllactosamine synthase
- Wheat germ agglutinin, a plant lectin that binds to this substrate
References
- ^ Kamel, M; Hanafi, M; Bassiouni, M (1991). "Inhibition of elastase enzyme release from human polymorphonuclear leukocytes by N-acetyl-galactosamine and N-acetyl-glucosamine". Clinical and experimental rheumatology 9 (1): 17–21. PMID 2054963. edit
- ^ "Sugar supplement may treat immune disease - health - 07 June 2007 - New Scientist". Retrieved 2007-06-08.
- ^ "Glucosamine-Like Supplement Suppresses Multiple Sclerosis Attacks, Study Suggests". Science Daily.
External links
|
Microbiology: Bacteria
|
|
Pathogenic
bacteria |
- Bacterial disease
- Coley's Toxins
- Exotoxin
- Lysogenic cycle
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|
| Human flora |
- Gut flora
- Skin flora
- Vaginal flora
|
|
Substrate
preference |
- Lipophilic
- Saccharophilic
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|
Oxygen
preference |
- Aerobic
- Anaerobic
- Microaerophile
- Nanaerobe
- Aerotolerant
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|
| Structures |
|
Cell
envelope
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- Cell membrane
- Cell wall: Peptidoglycan
- Gram-positive bacteria only: Teichoic acid
- Lipoteichoic acid
- Endospore
- Gram-negative bacteria only: Bacterial outer membrane
- Periplasmic space
- Mycobacteria only: Arabinogalactan
- Mycolic acid
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|
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Outside
envelope
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- Bacterial capsule
- Slime layer
- S-layer
- Glycocalyx
- Pilus
- Fimbria
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|
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Composite
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|
|
|
| Shapes |
- Bacterial cellular morphologies
- L-form bacteria
- Coccus
- Bacillus
- Coccobacillus
- Spiral
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Index of bacterial disease
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|
| Description |
|
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| Disease |
- Gram-positive firmicutes
- Gram-positive actinobacteria
- Tuberclosis
- Gram-negative proteobacteria
- Cholera
- Gram-negative non-proteobacteria
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|
| Treatment |
- Antibiotics
- cell wall
- nucleic acid
- myocbacteria
- protein synthesis
- Vaccines
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|
|
UpToDate Contents
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English Journal
- A continuous fluorescent enzyme assay for early steps of lipid A biosynthesis.
- Jenkins RJ, Dotson GD.SourceDepartment of Medicinal Chemistry, College of Pharmacy, University of Michigan, Ann Arbor, MI 48109, USA.
- Analytical biochemistry.Anal Biochem.2012 Jun 1;425(1):21-7. Epub 2012 Feb 28.
- UDP-N-acetylglucosamine acyltransferase (LpxA) and UDP-3-O-(R-3-hydroxyacyl)-glucosamine acyltransferase (LpxD) catalyze the first and third steps of lipid A biosynthesis, respectively. Both enzymes have been found to be essential for survival among gram-negative bacteria that synthesize lipopolysac
- PMID 22381368
- Engulfment and clearance of apoptotic cells based on a GlcNAc-binding lectin-like property of surface vimentin.
- Ise H, Goto M, Komura K, Akaike T.SourceFrontier Research Center, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8503, Japan.
- Glycobiology.Glycobiology.2012 Jun;22(6):788-805. Epub 2012 Feb 17.
- The clearance of apoptotic cells is important to maintain tissue homeostasis. The engulfment of apoptotic cells is performed by professional phagocytes, such as macrophages, and also by non-professional phagocytes, such as mesenchymal cells. Here, we show that vimentin, a cytoskeletal protein, funct
- PMID 22345628
Japanese Journal
- Increased sugar uptake promotes oncogenesis via EPAC/RAP1 and O-GlcNAc pathways
- Onodera Yasuhito,Nam Jin-Min,Bissell Mina J.
- Journal of clinical investigation 124(1), 367-384, 2014-01-02
- … Loss of epithelial integrity involved activation of RAP1 via exchange protein directly activated by cAMP (EPAC), involving also O-linked N-acetylglucosamine modification downstream of the hexosamine biosynthetic pathway. …
- NAID 120005372327
- 地域糖質資源を活用した機能性食品・素材の開発(応用糖質科学シンポジウム)
- 戸谷 一英,古関 健一,中川 裕子 [他],長田 光正,二階堂 満
- 応用糖質科学 : 日本応用糖質科学会誌 3(2), 159-165, 2013-05-20
- 三陸の水産加工業は地域水産資源をそのまま一次加工して出荷してきたが,東日本大震災からの復興には更なる高付加価値化が必要である。本特集では三陸のキチン系糖質資源の有効利用を紹介する。N-アセチルグルコサミン(NAG)は関節症痛軽減効果で知られ,甲殻(カニ・エビ殻)から精製したα-キチンの塩酸分解等により製造される。我々はα-キチンの前処理(メカノケミカル粉砕や水熱処理)により酵素分解率を向上させてき …
- NAID 110009625722
- BIO R&D キチン分解細菌Chitiniphilus shinanonensis由来の新規キチン分解酵素を用いたN-アセチルグルコサミンの生産
Related Links
- N-Acetylglucosamine (N-acetyl-D-glucosamine, or GlcNAc, or NAG) is a monosaccharide derivative of glucose. It is an amide between glucosamine and acetic acid. It has a molecular formula of C8H15NO6, a molar mass of 221.21 g/ mol, and ...
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