2-Acetamido-2-deoxy-D-glucose

• CAT Number: R065265
• CAS Number: 7512-17-6
• Molecular Formula: C8H15NO6
• Molecular Weight: 221.2
• Purity: ≥95%
• Storage: -20°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
• InChIKey: MBLBDJOUHNCFQT-UIYHXYAWSA-N
• SMILES: O=CC(NC(=O)C)C(O)C(O)[C@H](O)CO

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%).

Reference

1:One-pot enzymatic production of 2-acetamido-2-deoxy-D-galactose (GalNAc) from 2-acetamido-2-deoxy-D-glucose (GlcNAc). Inoue K, Nishimoto M, Kitaoka M.Carbohydr Res. 2011 Nov 8;346(15):2432-6. doi: 10.1016/j.carres.2011.08.032. Epub 2011 Sep 8. PMID: 21955790 2:Unique cleavage of 2-acetamido-2-deoxy-D-glucose from the reducing end of biantennary complex type oligosaccharides. Murase T, Kajihara Y.Carbohydr Res. 2010 Aug 16;345(12):1702-7. doi: 10.1016/j.carres.2010.05.020. Epub 2010 Jun 1. PMID: 20580347 3:Novel and facile synthesis of furanodictines A and B based on transformation of 2-acetamido-2-deoxy-D-glucose into 3,6-anhydro hexofuranoses. Ogata M, Hattori T, Takeuchi R, Usui T.Carbohydr Res. 2010 Jan 26;345(2):230-4. doi: 10.1016/j.carres.2009.10.007. Epub 2009 Dec 2. PMID: 19962133 4:Biological evaluation of a series of 2-acetamido-2-deoxy-D-glucose analogs towards cellular glycosaminoglycan and protein synthesis in vitro. Berkin A, Szarek WA, Kisilevsky R.Glycoconj J. 2005 Nov;22(7-9):443-51. PMID: 16311889 5:Quantitative production of 2-acetamido-2-deoxy-D-glucose from crystalline chitin by bacterial chitinase. Pichyangkura R, Kudan S, Kuttiyawong K, Sukwattanasinitt M, Aiba S.Carbohydr Res. 2002 Mar 15;337(6):557-9. PMID: 11890893 6:Utilization of commercial non-chitinase enzymes from fungi for preparation of 2-acetamido-2-deoxy-D-glucose from beta-chitin. Sukwattanasinitt M, Zhu H, Sashiwa H, Aiba S.Carbohydr Res. 2002 Feb 5;337(2):133-7. PMID: 11814444 7:Synthesis of some 2-methylthiouracil nucleosides and its 5-halo analogues of 2-acetamido-2-deoxy-D-glucose. Abdel-Rahman AA.Pharmazie. 2001 Oct;56(10):773-6. PMID: 11683120 8:Synthesis of 4-deoxy-4-fluoro analogues of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-galactose and their effects on cellular glycosaminoglycan biosynthesis. Berkin A, Szarek WA, Kisilevsky R.Carbohydr Res. 2000 Jun 30;326(4):250-63. PMID: 10890273 9:Synthesis of 4-deoxy analogues of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-xylose and their effects on glycoconjugate biosynthesis. Berkin A, Szarek MA, Plenkiewicz J, Szarek WA, Kisilevsky R.Carbohydr Res. 2000 Mar 24;325(1):30-45. PMID: 10741825 10:Cloning of a human UDP-galactose:2-acetamido-2-deoxy-D-glucose 3beta-galactosyltransferase catalyzing the formation of type 1 chains. Kolbinger F, Streiff MB, Katopodis AG.J Biol Chem. 1998 Jan 2;273(1):433-40. PMID: 9417100 Free Article