A monosaccharide intermediate of the hexosamine biosynthetic pathway
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D-Glucosamine-6-phosphate (hydrate)

Item No. 30869

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-amino-2-deoxy-D-glucose-6 (dihydrogen phosphate), hydrate
Synonyms
  • D-GlcN-6-P
Molecular Formula
C6H14NO8P • XH2O
Formula Weight
259.2
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 10 mg/ml
SMILES
OP(OC[C@H]([C@H]([C@@H]([C@H](C=O)N)O)O)O)(O)=O.O
InChi Code
InChI=1S/C6H14NO8P.H2O/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);1H2/t3-,4+,5+,6+;/m0./s1
InChi Key
UQENKMRQSJRGCB-BTVCFUMJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    50 mg

    $69

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    100 mg

    $120

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    250 mg

    $280

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    Product Description

    D-Glucosamine-6-phosphate (D-GlcN-6-P) is a monosaccharide intermediate of the hexosamine biosynthetic pathway.1 It is formed from D-fructose-6-phosphate by glucosamine-6-phosphate synthase (GlmS) in the presence of glutamine or from D-glucosamine (Item No. 27055) by N-acetyl-D-glucosamine (GlcNAc) kinase.2,3,4 D-GlcN-6-P binds the GlmS riboswitch (Ki = 380 µM), a ribozyme located in the 5'-UTR of the gene encoding GlmS that, when bound by D-GlcN-6-P, inhibits GlmS production and decreases D-GlcN-6-P levels.3,5 It is a precursor in the biosynthesis of uridine diphosphate-N-acetylglucosamine (UDP-GlcNAc), a substrate for protein glycosylation and a component of bacterial cell walls.4,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Buse, M.G. Hexosamines, insulin resistance, and the complications of diabetes: Current status. Am. J. Physiol. Endocrinol. Metab. 290(1), E1-E8 (2006).

    2. Bearne, S.L., and Blouin, C. Inhibition of Escherichia coli glucosamine-6-phosphate synthase by reactive intermediate analogues. The role of the 2-amino function in catalysis. The Journal of Biological Chemisty 275(1), 135-140 (2000).

    3. Akella, N.M., Ciraku, L., and Reginato, M.J. Fueling the fire: Emerging role of the hexosamine biosynthetic pathway in cancer. BMC Biol. 17(1), 52 (2019).

    4. Chiaradonna, F., Ricciardiello, F., and Palorini, R. The nutrient-sensing hexosamine biosynthetic pathway as the hub of cancer metabolic rewiring. Cells 7(6), 53 (2018).

    5. Cochrane, J.C., Lipchock, S.V., and Strobel, S.A. Structural investigation of the GlmS ribozyme bound to its catalytic cofactor. Chem. Biol. 14(1), 97-105 (2007).

    6. Rodríguez-Díaz, J., Rubio-Del-Campo, A., and Yebra, M.J. Regulatory insights into the production of UDP-N-acetylglucosamine by Lactobacillus casei. Bioengineered 3(6), 339-342 (2012).