同: N-acetyl-D-glucosamine

関: See N-Acetylglucosamine (GlcNAc)

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/10/30 18:14:42」(JST)

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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]

Medical uses

It has been proposed as a treatment for autoimmune diseases,^[2] and recent tests have claimed some success.^[3]

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

Re Multiple Sclerosis

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English Journal

Detecting O-GlcNAc using in vitro sulfation.

Wu ZL1, Robey MT2, Tatge T2, Lin C3, Leymarie N3, Zou Y2, Zaia J4.
Glycobiology.Glycobiology.2014 Aug;24(8):740-7. doi: 10.1093/glycob/cwu037. Epub 2014 May 5.
O-linked β-N-acetylglucosamine (O-GlcNAc) glycosylation, the covalent attachment of N-acetylglucosamine to serine and threonine residues of proteins, is a post-translational modification that shares many features with protein phosphorylation. O-GlcNAc is essential for cell survival and plays import
PMID 24799377

Structural change of N-glycan exposes hydrophobic surface of human transferrin.

Nagae M1, Morita-Matsumoto K1, Arai S2, Wada I2, Matsumoto Y3, Saito K3, Hashimoto Y4, Yamaguchi Y5.
Glycobiology.Glycobiology.2014 Aug;24(8):693-702. doi: 10.1093/glycob/cwu033. Epub 2014 Apr 28.
Transferrin is an iron-transport protein which possesses N-glycans at Asn432 and Asn630 in humans. Transferrin glycoforms Tf-1 and Tf-2, previously identified in human cerebrospinal fluid, are defined as the lower and upper bands in gel electrophoresis, respectively. Importantly, the Tf-2/Tf-1 ratio
PMID 24780636

O-GlcNAcylation is increased in prostate cancer tissues and enhances malignancy of prostate cancer cells.

Gu Y1, Gao J2, Han C1, Zhang X1, Liu H1, Ma L1, Sun X2, Yu W1.
Molecular medicine reports.Mol Med Rep.2014 Aug;10(2):897-904. doi: 10.3892/mmr.2014.2269. Epub 2014 May 26.
O-GlcNAc is an O-linked -N-acetylglucosamine moiety attached to the side-chain hydroxyl of a serine or threonine residue in numerous cytoplasmic and nuclear proteins. In this study, we detected the level of O-GlcNAc in prostate, liver and pancreatic cancer tissues, and found that the global O-GlcNA
PMID 24865644

Japanese Journal

レセプター擬似分子による新しいヒトインフルエンザウイルス吸着素材の開発と応用

鈴木康夫スズキヤスオSuzuki Yasuo
総合工学 26, 15, 2014-03
… It contains N-acetylneuraminic acidα2-6Galβ1-4GlcNAc sugar, polyglutamic acid and alkyl chain. …
NAID 120005428817

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
There is a considerable resurgence of interest in the role of aerobic glycolysis in cancer; however, increased glycolysis is frequently viewed as a consequence of oncogenic events that drive malignant …
NAID 120005372327

Intracellular lectins are involved in quality control of glycoproteins

YAMAMOTO Kazuo
Proceedings of the Japan Academy, Series B 90(2), 67-82, 2014
… After correctly folded glycoproteins are transported to the Golgi apparatus, N-glycans are trimmed into Man3GlcNAc2 and then rebuilt into various complex-type glycans in the Golgi, resulting in the addition of diverse sugar structures that allow glycoproteins to play various roles outside of the cells. …
NAID 130003392354

Related Pictures

★リンクテーブル★

リンク元	「ペプチドグリカン」「N-アセチルグルコサミン」「N-アセチル-D-グルコサミン」

「ペプチドグリカン」

N-Acetylglucosamine
	IUPAC name 2-(Acetylamino)-2-deoxy-D-glucose
	Other names N-Acetyl-D-Glucosamine; GlcNAc; NAG
Identifiers
CAS number	7512-17-6
PubChem	24139
ChemSpider	22563
UNII	V956696549
ChEBI	CHEBI:28009
ChEMBL	CHEMBL447878
Jmol-3D images	Image 1
	SMILES O=C(N[C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@H]1O)CO)C ;
	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 ; Key: OVRNDRQMDRJTHS-FMDGEEDCSA-N ;
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)
	(verify) (what is: /?)
	Infobox references

　　[★]

英: peptidoglycan
同: ムレイン murein
関

細菌の細胞壁成分
グラム陽性菌には厚く、グラム陰性菌には薄く存在する
N-アセチルグルコサミン(NAG, GlcNAc)、N-アセチルムラミン酸(NAM, MurNAc)が直鎖状に連結。この鎖にNAM+L-Ala+D-Glu+L-Lys+D-Ala+NAM?

「N-アセチルグルコサミン」

　　[★]

英: N-acetylglucosamine, N-acetyl glucosamine, GlcNAc, NAG
同: N-アセチル-D-グルコサミン N-acetyl-D-glucosamine、N-アセチルキトサミン N-acetylchitosamine
関: N-アセチルグルコサミニダーゼ

「N-アセチル-D-グルコサミン」

　　[★] N-アセチルグルコサミン

同: GlcNAc, NAG

[1] 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

[2] "Sugar supplement may treat immune disease - health - 07 June 2007 - New Scientist". Retrieved 2007-06-08.

[3] "Glucosamine-Like Supplement Suppresses Multiple Sclerosis Attacks, Study Suggests". Science Daily.

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案内

案内

GlcNAc