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Key Documents

A3286

Sigma-Aldrich

N-Acetyl-D-glucosamine

BioReagent, suitable for cell culture

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C8H15NO6
CAS Number:
Molecular Weight:
221.21
Beilstein/REAXYS Number:
1727589
EC Number:
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.75

product line

BioReagent

Quality Level

assay

≥95% (HPLC)

form

powder

technique(s)

cell culture | mammalian: suitable

mp

211 °C (dec.) (lit.)

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), a derivative of glucose is a monosaccharide. It is a white powder and is mildly sweet. It melts at 221°C. GlcNAc is 25% soluble in water. It is present in bromelain, ricin agglutinin and abrus agglutinin, in plants. In humans, it is present in tissue plasminogen activator, growth factors and hormones.

Application

N-Acetyl-D-glucosamine addition has been used:
  • as a substrate to develop dot-blots
  • as a substrate to reveal alkaline phosphatase in the immunohistochemical analysis
  • to detect specific immune complexes in western blot analysis

Biochem/physiol Actions

N-Acetylglucosamine (GlcNAc) oligomer may have the ability to initiate factors for canine polymorphonuclear cells (PMN) in vivo. It possesses wound healing and chemotactic activity. GlcNAc and its derivatives are usually employed in preparing dietary supplements and also used in therapeutic development.

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)


Certificates of Analysis (COA)

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Effect of N-acetyl-d-glucosamine and d-glucosamine oligomers on canine polymorphonuclear cells in vitro
Usami Y, et al.
Carbohydrate Polymers, 36(2-3), 137-141 (1998)
Glycoprofiling effects of media additives on IgG produced by CHO cells in fed-batch bioreactors
Kildegaard H F, et al.
Biotechnology and Bioengineering, 113(2), 359-366 (2016)
Glucose metabolism and hexosamine pathway regulate oncogene-induced senescence
Gitenay D, et al.
Cell Death & Disease, 5(2), e1089-e1089 (2014)
Cumulus expansion, nuclear maturation and connexin 43, cyclooxygenase-2 and FSH receptor mRNA expression in equine cumulus-oocyte complexes cultured in vitro in the presence of FSH and precursors for hyaluronic acid synthesis
Dell'Aquila M E, et al.
Reproductive Biology and Endocrinology, 2(1), 44-44 (2004)
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

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