Acetylglucosamine
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MedKoo CAT#: 326969

CAS#: 7512-17-6

Description: Acetylglucosamine or N-acetylglucosamine is potentially for the treatment of irritable bowel syndrome. N-Acetylglucosamine (GlcNAc) is a monosaccharide that usually polymerizes linearly through (1,4)-β-linkages. GlcNAc is the monomeric unit of the polymer chitin, the second most abundant carbohydrate after cellulose. In addition to serving as a component of this homogeneous polysaccharide, GlcNAc is also a basic component of hyaluronic acid and keratin sulfate on the cell surface. GlcNAc has been reported to be an inhibitor of elastase release from human polymorphonuclear leukocytes (range 8–17% inhibition), however this is much weaker than the inhibition seen with N-acetylgalactosamine (range 92–100%).


Chemical Structure

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Acetylglucosamine
CAS# 7512-17-6

Theoretical Analysis

MedKoo Cat#: 326969
Name: Acetylglucosamine
CAS#: 7512-17-6
Chemical Formula: C8H15NO6
Exact Mass: 221.0899
Molecular Weight: 221.209
Elemental Analysis: C, 43.44; H, 6.84; N, 6.33; O, 43.40

Price and Availability

Size Price Availability Quantity
5.0g USD 350.0 2 Weeks
20.0g USD 550.0 2 Weeks
50.0g USD 950.0 2 Weeks
100.0g USD 1650.0 2 Weeks
500.0g USD 2950.0 2 Weeks
1.0kg USD 5250.0 2 Weeks
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Synonym: Acetylglucosamine; GlcNAc; Bio-NAG; GreenNAG; Marine Sweet; N-Acetyl-D-glucosamine; N-Acetylglucosamine; NSC 400525; NSC 524344.

IUPAC/Chemical Name: N-Acetyl-beta-D-glucosamine

InChi Key: OVRNDRQMDRJTHS-FMDGEEDCSA-N

InChi Code: 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

SMILES Code: O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)NC(C)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 221.209 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Ogawa M, Sawaguchi S, Kamemura K, Okajima T. Intracellular and extracellular O-linked N-acetylglucosamine in the nervous system. Exp Neurol. 2015 Dec;274(Pt B):166-74. doi: 10.1016/j.expneurol.2015.08.009. Epub 2015 Aug 14. Review. PubMed PMID: 26278182.

2: Naseem S, Konopka JB. N-acetylglucosamine Regulates Virulence Properties in Microbial Pathogens. PLoS Pathog. 2015 Jul 30;11(7):e1004947. doi: 10.1371/journal.ppat.1004947. eCollection 2015 Jul. Review. PubMed PMID: 26226264; PubMed Central PMCID: PMC4520607.

3: Olivier-Van Stichelen S, Hanover JA. You are what you eat: O-linked N-acetylglucosamine in disease, development and epigenetics. Curr Opin Clin Nutr Metab Care. 2015 Jul;18(4):339-45. doi: 10.1097/MCO.0000000000000188. Review. PubMed PMID: 26049631; PubMed Central PMCID: PMC4479189.

4: Guo H, Xiang J. [Influence of poly-β-1-6-N-acetylglucosamine on biofilm formation and drug resistance of Acinetobacter baumannii]. Zhonghua Shao Shang Za Zhi. 2015 Feb;31(1):45-7. Review. Chinese. PubMed PMID: 25876639.

5: Ogawa M, Sawaguchi S, Furukawa K, Okajima T. N-acetylglucosamine modification in the lumen of the endoplasmic reticulum. Biochim Biophys Acta. 2015 Jun;1850(6):1319-24. doi: 10.1016/j.bbagen.2015.03.003. Epub 2015 Mar 17. Review. PubMed PMID: 25791024.

6: Ogawa M, Furukawa K, Okajima T. Extracellular O-linked β-N-acetylglucosamine: Its biology and relationship to human disease. World J Biol Chem. 2014 May 26;5(2):224-30. doi: 10.4331/wjbc.v5.i2.224. Review. PubMed PMID: 24921011; PubMed Central PMCID: PMC4050115.

7: Liu L, Liu Y, Shin HD, Chen R, Li J, Du G, Chen J. Microbial production of glucosamine and N-acetylglucosamine: advances and perspectives. Appl Microbiol Biotechnol. 2013 Jul;97(14):6149-58. doi: 10.1007/s00253-013-4995-6. Epub 2013 Jun 11. Review. PubMed PMID: 23754704.

8: Zhang J, Zhang L, Li X, Xu W. UDP-3-O-(R-3-hydroxymyristoyl)-N-acetylglucosamine deacetylase (LpxC) inhibitors: a new class of antibacterial agents. Curr Med Chem. 2012;19(13):2038-50. Review. PubMed PMID: 22414079.

9: Zachara NE. The roles of O-linked β-N-acetylglucosamine in cardiovascular physiology and disease. Am J Physiol Heart Circ Physiol. 2012 May 15;302(10):H1905-18. doi: 10.1152/ajpheart.00445.2011. Epub 2012 Jan 27. Review. PubMed PMID: 22287582; PubMed Central PMCID: PMC3362101.

10: Darley-Usmar VM, Ball LE, Chatham JC. Protein O-linked β-N-acetylglucosamine: a novel effector of cardiomyocyte metabolism and function. J Mol Cell Cardiol. 2012 Mar;52(3):538-49. doi: 10.1016/j.yjmcc.2011.08.009. Epub 2011 Aug 22. Review. PubMed PMID: 21878340; PubMed Central PMCID: PMC3928598.

11: Gautam A, Rishi P, Tewari R. UDP-N-acetylglucosamine enolpyruvyl transferase as a potential target for antibacterial chemotherapy: recent developments. Appl Microbiol Biotechnol. 2011 Oct;92(2):211-25. doi: 10.1007/s00253-011-3512-z. Epub 2011 Aug 7. Review. PubMed PMID: 21822642.

12: Chen JK, Shen CR, Liu CL. N-acetylglucosamine: production and applications. Mar Drugs. 2010 Sep 15;8(9):2493-516. doi: 10.3390/md8092493. Review. PubMed PMID: 20948902; PubMed Central PMCID: PMC2953398.

13: Chopra A. (99m)Tc-Labeled S-benzoylmercaptoacetyl triglycine n-acetylglucosamine. 2010 Apr 21 [updated 2010 May 13]. Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. Available from http://www.ncbi.nlm.nih.gov/books/NBK42929/ PubMed PMID: 20641990.

14: Butkinaree C, Park K, Hart GW. O-linked beta-N-acetylglucosamine (O-GlcNAc): Extensive crosstalk with phosphorylation to regulate signaling and transcription in response to nutrients and stress. Biochim Biophys Acta. 2010 Feb;1800(2):96-106. doi: 10.1016/j.bbagen.2009.07.018. Epub 2009 Aug 6. Review. PubMed PMID: 19647786; PubMed Central PMCID: PMC2815129.

15: Chatham JC, Marchase RB. The role of protein O-linked beta-N-acetylglucosamine in mediating cardiac stress responses. Biochim Biophys Acta. 2010 Feb;1800(2):57-66. doi: 10.1016/j.bbagen.2009.07.004. Epub 2009 Jul 14. Review. PubMed PMID: 19607882; PubMed Central PMCID: PMC2814923.

16: Ngoh GA, Jones SP. New insights into metabolic signaling and cell survival: the role of beta-O-linkage of N-acetylglucosamine. J Pharmacol Exp Ther. 2008 Dec;327(3):602-9. doi: 10.1124/jpet.108.143263. Epub 2008 Sep 3. Review. PubMed PMID: 18768779.

17: Golks A, Guerini D. The O-linked N-acetylglucosamine modification in cellular signalling and the immune system. 'Protein modifications: beyond the usual suspects' review series. EMBO Rep. 2008 Aug;9(8):748-53. doi: 10.1038/embor.2008.129. Epub 2008 Jul 11. Review. PubMed PMID: 18617890; PubMed Central PMCID: PMC2515212.

18: Hart GW, Housley MP, Slawson C. Cycling of O-linked beta-N-acetylglucosamine on nucleocytoplasmic proteins. Nature. 2007 Apr 26;446(7139):1017-22. Review. PubMed PMID: 17460662.

19: Musselmann K, Hassell JR. Focus on molecules: CHST6 (carbohydrate sulfotransferase 6; corneal N-acetylglucosamine-6-sulfotransferase). Exp Eye Res. 2006 Oct;83(4):707-8. Epub 2006 Mar 23. Review. PubMed PMID: 16549065.

20: Chou TY, Hart GW. O-linked N-acetylglucosamine and cancer: messages from the glycosylation of c-Myc. Adv Exp Med Biol. 2001;491:413-8. Review. PubMed PMID: 14533811.