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A4106

Sigma-Aldrich

N-Acetyl-D-glucosamine

≥95% (HPLC)

Synonym(s):

2-Acetamido-2-deoxy-D-glucose, D-GlcNAc

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About This Item

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:
329770850
NACRES:
NA.25

Assay

≥95% (HPLC)

form

powder

color

beige

mp

211 °C (dec.) (lit.)

solubility

water: 50 mg/mL, clear to cloudy, colorless to faintly yellow

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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Application

N-Acetyl-D-glucosamine (D-GlcNAc) is a derivitized glucose monomer found in polymers of bacterial cell walls, chitin, hyaluronic acids and various glycans. D-GlcNAc is used to identify, differentiate and characterize N-acetyl-β-D-hexoaminidase(s).

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.

Storage Class Code

11 - Combustible Solids

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
Bingwu Yu et al.
Journal of magnetic resonance (San Diego, Calif. : 1997), 228, 159-165 (2013-01-09)
Strong (1)H-(1)H coupling can significantly reduce the accuracy of (1)J(CH) measured from frequency differences in coupled HSQC spectra. Although accurate (1)J(CH) values can be extracted from spectral simulation, it would be more convenient if the same accurate (1)J(CH) values can
Yasuhito Onodera et al.
The Journal of clinical investigation, 124(1), 367-384 (2013-12-10)
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 cell growth and survival. Here we provide evidence that increased
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
Kirsi Rilla et al.
The Journal of biological chemistry, 288(8), 5973-5983 (2013-01-11)
Mammals have three homologous genes encoding proteins with hyaluronan synthase activity (Has1-3), all producing an identical polymer from UDP-N-acetylglucosamine and UDP-glucuronic acid. To compare the properties of these isoenzymes, COS-1 cells, with minor endogenous hyaluronan synthesis, were transfected with human
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