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Merck

G5875

α-D-Glucose 1,6-bisphosphate tetra(cyclohexylammonium) salt hydrate

≥95% dry basis

Synonym(s):

α-D-Glucose 1,6-diphosphate tetra(cyclohexylammonium) salt hydrate, Glc-1,6-PP.4CHA

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About This Item

Empirical Formula (Hill Notation):
C6H14O12P2 · 4C6H13N · xH2O
CAS Number:
71662-13-0
Molecular Weight:
736.81 (anhydrous basis)
NACRES:
NA.25
PubChem Substance ID:
24895234
UNSPSC Code:
12352201
EC Number:
275-777-4
MDL number:
MFCD00167199

Key Documents

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InChI key

DMUBREKUECBHKK-KMWDTYPGSA-N

InChI

1S/4C6H13N.C6H14O12P2.H2O/c4*7-6-4-2-1-3-5-6;7-3-2(1-16-19(10,11)12)17-6(5(9)4(3)8)18-20(13,14)15;/h4*6H,1-5,7H2;2-9H,1H2,(H2,10,11,12)(H2,13,14,15);1H2/t;;;;2-,3-,4+,5-,6-;/m....1./s1

SMILES string

[H]O[H].NC1CCCCC1.NC2CCCCC2.NC3CCCCC3.NC4CCCCC4.O[C@H]5[C@H](O)[C@@H](COP(O)(O)=O)O[C@H](OP(O)(O)=O)[C@@H]5O

biological source

synthetic

assay

≥95% dry basis

form

powder

color

white

solubility

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

storage temp.

−20°C

Quality Level

200

Related Categories

Application

Glucose-1,6-bisphosphate and fructose-1,6-bisphosphate were used as bisphosphorylated glycan standards in mass spectrometry analysis to determine if pyrophosphate ions observed in lipid A from Gram-negative bacteria were artifacts produced by condensation of two phosphate groups in the dissociating ion. α-D-Glucose 1,6-bisphosphate is used in the identification, differentiation and characterization of α-phosphoglucomutase(s), β-phosphoglucomutas(s) and α- and β-hexoglucomutase(s).
a-D-Glucose 1,6-bisphosphate is used in the identification, differentiation and characterization of a-phosphoglucomutase(s), β-phosphoglucomutase(s) and a- and β-hexoglucomutase(s).

Biochem/physiol Actions

Glucose-1,6-bisphosphate and fructose-1,6-bisphosphate were used as bisphosphorylated glycan standards in mass spectrometry analysis to determine if pyrophosphate ions observed in lipid A from Gram-negative bacteria were artifacts produced by condensation of two phosphate groups in the dissociating ion.
Metabolite formed via the activity of Glucose-1,6-biphosphate synthase. Glucose-1,6-biphosphate (G-1,6-BP) acts as an inhibitor of hexokinase function and an activator of phosphofructokinase-1 and pyruvate kinase. G-1,6-BP also acts as a coenzyme for phosphoglucomutate and a cofactor for phosphopentomutase.

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

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SLCB2113
SLCB0733
SLBV3928
SLBL5562V
SLBC6889V

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Jace W Jones et al.
Proceedings of the National Academy of Sciences of the United States of America, 105(35), 12742-12747 (2008-08-30)
Lipid A isolated from several bacteria (Escherichia coli, Pseudomonas aeruginosa, Salmonella enterica, and various strains of Yersinia) showed abundant formation of pyrophosphate anions upon ion dissociation. Pyrophosphate [H(3)P(2)O(7)](-) and/or [HP(2)O(6)](-) anions were observed as dominant fragments from diphosphorylated lipid A

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