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MetaCyc Compound Class: D-glucosamine 6-phosphate

Synonyms: D-glucosamine phosphate, D-glucosamine 6-phosphate, D-glucosamine-6-P

D-glucosamine 6-phosphate compound structure

Chemical Formula: C6H13NO8P

Instances:
α-D-glucosamine 6-phosphate

Molecular Weight: 258.14 Daltons

Monoisotopic Molecular Weight: 259.0457029414 Daltons

SMILES: C(OP([O-])(=O)[O-])C1(OC(O)C([N+])C(O)C(O)1)

InChI: InChI=1S/C6H14NO8P/c7-3-5(9)4(8)2(15-6(3)10)1-14-16(11,12)13/h2-6,8-10H,1,7H2,(H2,11,12,13)/p-1/t2-,3-,4-,5-,6?/m1/s1

InChIKey: InChIKey=XHMJOUIAFHJHBW-IVMDWMLBSA-M

Unification Links: CAS:3616-42-0 , HMDB:HMDB01254 , IAF1260:34709 , KEGG:C00352

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -262.3175 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

UDP-N-acetyl-D-galactosamine biosynthesis II , UDP-N-acetyl-D-glucosamine biosynthesis II :
D-glucosamine 6-phosphate + acetyl-CoA → N-acetyl-D-glucosamine 6-phosphate + coenzyme A + H+

Reactions known to produce the compound:

anhydromuropeptides recycling , N-acetylglucosamine degradation I :
N-acetyl-D-glucosamine 6-phosphate + H2O → D-glucosamine 6-phosphate + acetate

chitin degradation I (archaea) :
D-glucosamine + ADP → D-glucosamine 6-phosphate + AMP + H+

chitin derivatives degradation :
D-glucosamine + ATP → D-glucosamine 6-phosphate + ADP + H+
N-acetyl-D-glucosamine 6-phosphate + H2O → D-glucosamine 6-phosphate + acetate
chitobiose 6'-phosphate + H2O → D-glucosamine + D-glucosamine 6-phosphate

Reactions known to both consume and produce the compound:

anhydromuropeptides recycling :
D-glucosamine 6-phosphate ↔ D-glucosamine 1-phosphate

CMP-legionaminate biosynthesis I :
β-D-fructofuranose 6-phosphate + L-glutamine ↔ D-glucosamine 6-phosphate + L-glutamate
D-glucosamine 6-phosphate ↔ D-glucosamine 1-phosphate

UDP-N-acetyl-D-glucosamine biosynthesis I :
β-D-fructofuranose 6-phosphate + L-glutamine ↔ D-glucosamine 6-phosphate + L-glutamate
D-glucosamine 6-phosphate ↔ D-glucosamine 1-phosphate

UDP-N-acetyl-D-glucosamine biosynthesis II :
β-D-fructofuranose 6-phosphate + L-glutamine ↔ D-glucosamine 6-phosphate + L-glutamate

In Reactions of unknown directionality:

Not in pathways:
a phosphorylated phosphoglucosamine mutase + D-glucosamine 6-phosphate = glucosamine 1,6-diphosphate + a phosphoglucosamine mutase

In Transport reactions:
a [PTS enzyme I]-Nπ-phospho-L-histidine + D-glucosamine[periplasmic space]D-glucosamine 6-phosphate[cytosol] + a [PTS enzyme I]-L-histidine

Enzymes inhibited by D-glucosamine 6-phosphate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: glutamine:fructose-6-phosphate amidotransferase [Broschat02]

Inhibitor (Noncompetitive) of: N-acetylglucosamine-6-phosphate deacetylase [Souza97, White67]

Inhibitor (Mechanism unknown) of: glutamine synthetase [Woolfolk67, Comment 1]

This compound has been characterized as an alternative substrate of the following enzymes: D-galactosamine-6-phosphate deaminase/isomerase


References

Broschat02: Broschat KO, Gorka C, Page JD, Martin-Berger CL, Davies MS, Huang Hc HC, Gulve EA, Salsgiver WJ, Kasten TP (2002). "Kinetic characterization of human glutamine-fructose-6-phosphate amidotransferase I: potent feedback inhibition by glucosamine 6-phosphate." J Biol Chem 277(17);14764-70. PMID: 11842094

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Souza97: Souza JM, Plumbridge JA, Calcagno ML (1997). "N-acetylglucosamine-6-phosphate deacetylase from Escherichia coli: purification and molecular and kinetic characterization." Arch Biochem Biophys 1997;340(2);338-46. PMID: 9143339

White67: White RJ, Pasternak CA (1967). "The purification and properties of N-acetylglucosamine 6-phosphate deacetylase from Escherichia coli." Biochem J 1967;105(1);121-5. PMID: 4861885

Woolfolk67: Woolfolk CA, Stadtman ER (1967). "Regulation of glutamine synthetase. 3. Cumulative feedback inhibition of glutamine synthetase from Escherichia coli." Arch Biochem Biophys 118(3);736-55. PMID: 4860415


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Mon Aug 31, 2015, BIOCYC14B.