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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

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 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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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
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
Reflections on glycobiology.
S Roseman
The Journal of biological chemistry, 276(45), 41527-41542 (2001-09-13)
Christina E Lünse et al.
ACS chemical biology, 6(7), 675-678 (2011-04-14)
The glmS-riboswitch is unique among riboswitch families as it represents a metabolite-dependent ribozyme that undergoes self-cleavage upon recognition of glucosamin-6-phosphate. The glmS-riboswitch is located in the 5'-untranslated region of bacterial genes involved in cell wall biosynthesis. Therefore, this riboswitch represents
Phillip J McCown et al.
RNA (New York, N.Y.), 17(4), 728-736 (2011-03-04)
Self-cleaving glmS ribozymes selectively bind glucosamine-6-phosphate (GlcN6P) and use this metabolite as a cofactor to promote self-cleavage by internal phosphoester transfer. Representatives of the glmS ribozyme class are found in Gram-positive bacteria where they reside in the 5' untranslated regions
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