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G5509

Sigma-Aldrich

D-Glucosamine 6-phosphate

≥98% (TLC)

Synonym(s):

2-Amino-2-deoxyglucose 6-phosphate

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About This Item

Empirical Formula (Hill Notation):
C6H14NO8P
CAS Number:
3616-42-0
Molecular Weight:
259.15
MDL number:
MFCD00067382
UNSPSC Code:
12352201
PubChem Substance ID:
24895214
NACRES:
NA.25

biological source

natural (inorganic)

assay

≥98% (TLC)

form

powder

technique(s)

thin layer chromatography (TLC): suitable

impurities

≤10% water (Karl Fischer)

color

white

solubility

water: 50 mg/mL, clear to hazy, colorless to almost colorless

storage temp.

−20°C

SMILES string

NC(C=O)C(O)C(O)C(O)COP(O)(O)=O

InChI

1S/C6H14NO8P/c7-3(1-8)5(10)6(11)4(9)2-15-16(12,13)14/h1,3-6,9-11H,2,7H2,(H2,12,13,14)

InChI key

AEJSSXDYDSUOOZ-UHFFFAOYSA-N

Related Categories

General description

D-Glucosamine 6-phosphate, the natural form of glucosamine, is a monosaccharide produced during hexosamine biosynthesis pathway by the enzyme glucosamine-6-phosphate deaminase from the two substrates fructose 6-phosphate and glutamine.

Linkage

Stability is greater than that of the sodium salt.

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)

Certificates of Analysis (COA)

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Stanislav S Terekhov et al.
Science advances, 6(26), eaaz9861-eaaz9861 (2020-07-09)
Microbial communities are self-controlled by repertoires of lethal agents, the antibiotics. In their turn, these antibiotics are regulated by bioscavengers that are selected in the course of evolution. Kinase-mediated phosphorylation represents one of the general strategies for the emergence of
Reflections on glycobiology.
S Roseman
The Journal of biological chemistry, 276(45), 41527-41542 (2001-09-13)
James S Davies et al.
FEBS letters, 593(1), 52-66 (2018-11-10)
N-Acetylglucosamine-6-phosphate deacetylase (NagA) and glucosamine-6-phosphate deaminase (NagB) are branch point enzymes that direct amino sugars into different pathways. For Staphylococcus aureus NagA, analytical ultracentrifugation and small-angle X-ray scattering data demonstrate that it is an asymmetric dimer in solution. Initial rate experiments
Mark E Graham et al.
Organic & biomolecular chemistry, 10(13), 2545-2551 (2012-03-01)
A novel post-translational modification of threonine, β-N-acetylglucosaminyl-phosphate, was recently discovered on assembly protein AP180, a protein which plays a crucial role in clathrin coated vesicle formation in synaptic vesicle endocytosis (SVE). Herein, we report studies aimed at probing the effect
Marie Valerio-Lepiniec et al.
Archives of biochemistry and biophysics, 498(2), 95-104 (2010-04-27)
Glucosamine-6-phosphate synthase (GlmS) is responsible for the first and rate-limiting step in the hexosamine biosynthetic pathway. It catalyzes the conversion of D-fructose-6P (F6P) into D-glucosamine-6P (GlcN6P) using L-glutamine (Gln) as nitrogen donor (synthase activity) according to an ordered bi-bi process
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