N-acetyl-D-Glucosamine

Cayman Chemical Item Number 13136

NAG; NSC 524344; GlcNAc; Marine Sweet (CAS 7512-17-6)

N-acetyl-D-Glucosamine (CAS 7512-17-6)

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Description

N-acetyl-D-Glucosamine (GlcNAc) is a monosaccharide derivative of glucose. It is released by the action of O-GlcNAcase, in mammalian systems from proteins that have been post-translationally modified with O-GlcNAc. Levels of O-GlcNAcylation proteins from Alzheimer’s disease brain extracts are decreased as compared to that in controls, suggesting that release of GlcNAc may contribute to pathogenesis.1 In E. coli, GlcNAc induces the expression of multidrug exporter genes, indicating that this sugar can alter gene expression.1 GlcNAc is also the monomeric unit of chitin, which is found in fungi and many invertebrates, including crustaceans, insects, and nematodes. For this reason, chemicals that inhibit the incorporation of GlcNAc into chitin are cytotoxic to these organisms.

1 Liu, F., Iqbal, K., Grundke-Iqbal, I., et al. O-GlnNAcylation regulates phosphorylation of tau: A mechanism involved in Alzheimer’s disease. Proc Natl Acad Sci USA 101(29) 10804-10809 (2004).

Synonyms
  • NAG
  • NSC 524344
  • GlcNAc
  • Marine Sweet
Formal Name 2-​(acetylamino)-​2-​deoxy-​D-​glucose
CAS Number 7512-17-6
Molecular Formula C8H15NO6
Formula Weight 221.2
Formulation A crystalline solid
Purity ≥98%
Stability 2 years
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere
SMILES
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O=CC(NC(=O)​C)​C(O)​C(O)​[C@H]​(O)​CO
InCHI Code
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​1S/C8H15NO6/c1-4(12)​9-5(2-10)​7(14)​8(15)​6(13)​3-11/h2,5-8,11,13-15H,3H2,1H3,(H,9,12)​/t5?,6-,7-,8-/m1/s1
InCHI Key
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MBLBDJOUHNCFQT-UIYHXYAWSA-N

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Size Price Quantity Subtotal
500 mg $9.00 $0.00
1 g $17.00 $0.00
5 g $72.00 $0.00
10 g $126.00 $0.00
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Pricing updated 2014-04-16. Prices are subject to change without notice.

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