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A8625

Sigma-Aldrich

N-Acetyl-D-glucosamine

≥99% (HPLC)

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Synonym(s):
2-Acetamido-2-deoxy-D-glucose, D-GlcNAc
Empirical Formula (Hill Notation):
C8H15NO6
CAS Number:
7512-17-6
Molecular Weight:
221.21
Beilstein:
1727589
EC Number:
231-368-2
MDL number:
MFCD00061615
UNSPSC Code:
12352201
PubChem Substance ID:
24891348
NACRES:
NA.25

biological source

crab (red)

Quality Level

200

Assay

≥99% (HPLC)

form

powder

technique(s)

HPLC: suitable

color

white to off-white

mp

211 °C (dec.) (lit.)

solubility

H2O: 50 mg/mL, clear to very slightly hazy (colorless to faint yellow solution)

storage temp.

−20°C

SMILES string

CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O

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

InChI key

OVRNDRQMDRJTHS-RTRLPJTCSA-N

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General description

N-acetylglucosamine (GlcNAc) is the acetylated derivative of glucosamine (GlcN). It is an important component of proteoglycans, glycoproteins, glycosaminoglycans (GAGs), and other building units found in connective tissue.

Application

N-Acetyl-D-glucosamine has been used:
  • as sugar for competitive inhibition in lectin histochemistry
  • as a component in Barbour-Stonner-Kelly (BSK) medium for cultivating Borrelia burgdorferi spirochetes strains
  • as a component of binding buffer to suspend Streptococcus pneumoniae strains for inhibition assay to examine the specificity of M-ficolin binding to S. pneumoniae strains

Biochem/physiol Actions

N-acetylglucosamine (GlcNAc) is mainly used in the food, cosmetics, and pharmaceutical industries.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Colette Cywes-Bentley et al.
Proceedings of the National Academy of Sciences of the United States of America, 110(24), E2209-E2218 (2013-05-30)
Microbial capsular antigens are effective vaccines but are chemically and immunologically diverse, resulting in a major barrier to their use against multiple pathogens. A β-(1→6)-linked poly-N-acetyl-d-glucosamine (PNAG) surface capsule is synthesized by four proteins encoded in genetic loci designated intercellular
Lucy G Weaver et al.
Carbohydrate research, 371, 68-76 (2013-03-26)
Poly-N-acetylglucosamine (PNAG) saccharides are an important constituent of bacterial biofilms, such as those produced by Staphylococcus aureus. We have developed a simple two-step iterative method for the synthesis of β-(1→6)-glucosamine oligosaccharides that are structurally similar to PNAG. We illustrate the
Mikkel Girke Jørgensen et al.
Genes & development, 27(10), 1132-1145 (2013-05-15)
Many bacterial small RNAs (sRNAs) regulate gene expression through base-pairing with mRNAs, and it has been assumed that these sRNAs act solely by this one mechanism. Here we report that the multicellular adhesive (McaS) sRNA of Escherichia coli uniquely acts
Jason M Berk et al.
The Journal of biological chemistry, 288(42), 30192-30209 (2013-09-10)
Emerin, a membrane component of nuclear "lamina" networks with lamins and barrier to autointegration factor (BAF), is highly O-GlcNAc-modified ("O-GlcNAcylated") in mammalian cells. Mass spectrometry analysis revealed eight sites of O-GlcNAcylation, including Ser-53, Ser-54, Ser-87, Ser-171, and Ser-173. Emerin O-GlcNAcylation
N-acetylglucosamine: a new osmotic solute in peritoneal dialysis solutions.
A Breborowicz et al.
Peritoneal dialysis international : journal of the International Society for Peritoneal Dialysis, 17 Suppl 2, S80-S83 (1997-01-01)
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