Metabolic Modeling Tutorial
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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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MetaCyc Compound Class: D-glucosamine 6-phosphate

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

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

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 1-phosphate ↔ D-glucosamine 6-phosphate

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

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

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

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]


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 18.5 on Sun Nov 23, 2014, BIOCYC13A.