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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)

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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
Gerald W Hart et al.
Nature, 446(7139), 1017-1022 (2007-04-27)
All animals and plants dynamically attach and remove O-linked beta-N-acetylglucosamine (O-GlcNAc) at serine and threonine residues on myriad nuclear and cytoplasmic proteins. O-GlcNAc cycling, which is tightly regulated by the concerted actions of two highly conserved enzymes, serves as a
A Cassone et al.
Microbiologica, 8(1), 85-99 (1985-01-01)
N-acetylglucosamine is a morphogenic effector in the human pathogenic yeast Candida albicans. Depending on temperature, N-acetylglucosamine induces yeast-mycelial conversion or chlamydospore formation. N-acetylglucosamine is also a carbon source for growth in the yeast form. Germ-tube formation, i.e. the intermediary of
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