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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:
Molecular Weight:
221.21
Beilstein/REAXYS Number:
1727589
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25

biological source

crab (red)

Quality Level

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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This Item
A4106A3286PHR1432
vibrant-m

A8625

N-Acetyl-D-glucosamine

vibrant-m

A4106

N-Acetyl-D-glucosamine

vibrant-m

A3286

N-Acetyl-D-glucosamine

vibrant-m

PHR1432

N-Acetylglucosamine

solubility

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

solubility

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

solubility

-

solubility

-

biological source

crab (red)

biological source

-

biological source

-

biological source

-

assay

≥99% (HPLC)

assay

≥95% (HPLC)

assay

≥95% (HPLC)

assay

-

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

300

mp

211 °C (dec.) (lit.)

mp

211 °C (dec.) (lit.)

mp

211 °C (dec.) (lit.)

mp

211 °C (dec.) (lit.)

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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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
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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