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MetaCyc Compound Class: N-acetyl-D-glucosamine 6-phosphate

Synonyms: N-acetylglucosamine-6-P, GlcNAc-6-P, N-acetyl-D-glucosamine-6-P, N-acetyl-glucosamine 6-phosphate, N-acetyl-glucosamine-6-P

Superclasses: all carbohydratesa carbohydratea glycana carbohydrate derivativea sugar phosphatea sugar 6-phosphate

<i>N</i>-acetyl-D-glucosamine 6-phosphate compound structure

Chemical Formula: C8H14NO9P

N-acetyl-α-D-glucosamine 6-phosphate,
N-acetyl-β-D-glucosamine 6-phosphate

Molecular Weight: 299.17 Daltons

Monoisotopic Molecular Weight: 301.0562676277 Daltons

SMILES: CC(=O)NC1(C(O)OC(COP([O-])(=O)[O-])C(O)C(O)1)

InChI: InChI=1S/C8H16NO9P/c1-3(10)9-5-7(12)6(11)4(18-8(5)13)2-17-19(14,15)16/h4-8,11-13H,2H2,1H3,(H,9,10)(H2,14,15,16)/p-2/t4-,5-,6-,7-,8?/m1/s1

Unification Links: CAS:102029-88-9, ChEBI:57513, HMDB:HMDB02817, IAF1260:34733, KEGG:C00357, PubChem:25243963

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -282.58258Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

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

Not in pathways:
a sugar phosphate + H2O → a sugar + phosphate

Reactions known to produce the compound:

chitin derivatives degradation , N-acetylglucosamine degradation II :
N-acetyl-β-D-glucosamine + ATP → N-acetyl-D-glucosamine 6-phosphate + ADP + H+

chitobiose degradation :
N-monoacetylchitobiose 6'-phosphate + H2O → N-acetyl-D-glucosamine 6-phosphate + D-glucosamine

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 both consume and produce the compound:

anhydromuropeptides recycling :
N-acetyl-β-muramate 6-phosphate + H2O ↔ N-acetyl-D-glucosamine 6-phosphate + (R)-lactate

chitin derivatives degradation , UDP-N-acetyl-D-galactosamine biosynthesis II , UDP-N-acetyl-D-glucosamine biosynthesis II :
N-acetyl-D-glucosamine 6-phosphateN-acetyl-α-D-glucosamine 1-phosphate

N-acetylneuraminate and N-acetylmannosamine degradation I :
N-acetyl-D-mannosamine 6-phosphate ↔ N-acetyl-D-glucosamine 6-phosphate

In Reactions of unknown directionality:

Not in pathways:
N,N'-diacetylchitobiose 6'-phosphate + H2O = N-acetyl-D-glucosamine 6-phosphate + N-acetyl-β-D-glucosamine
a phosphorylated phosphoacetylglucosamine mutase + N-acetyl-D-glucosamine 6-phosphate = N-acetyl-D-glucosamine 1,6-bisphosphate + a phosphoacetylglucosamine mutase

In Transport reactions:
a [PTS enzyme I]-Nπ-phospho-L-histidine + N-acetyl-D-glucosamine[periplasm]N-acetyl-D-glucosamine 6-phosphate[cytosol] + a [PTS enzyme I]-L-histidine,
a [PTS enzyme I]-Nπ-phospho-L-histidine + a sugar[out] → a [PTS enzyme I]-L-histidine + a sugar phosphate[in]

Enzymes activated by N-acetyl-D-glucosamine 6-phosphate, sorted by the type of activation, are:

Activator (Allosteric) of: glucosamine-6-phosphate deaminase [White67, Altamirano92, Comment 1]

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

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

This compound has been characterized as an alternative substrate of the following enzymes: N-acetylgalactosamine-6-phosphate deacetylase

Revised 21-Nov-2013 by Caspi R, SRI International


Altamirano92: Altamirano MM, Plumbridge JA, Calcagno ML (1992). "Identification of two cysteine residues forming a pair of vicinal thiols in glucosamine-6-phosphate deaminase from Escherichia coli and a study of their functional role by site-directed mutagenesis." Biochemistry 31(4);1153-8. PMID: 1734962

Altamirano94: Altamirano MM, Hernandez-Arana A, Tello-Solis S, Calcagno ML (1994). "Spectrochemical evidence for the presence of a tyrosine residue in the allosteric site of glucosamine-6-phosphate deaminase from Escherichia coli." Eur J Biochem 1994;220(2);409-13. PMID: 8125098

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

Calcagno84: Calcagno M, Campos PJ, Mulliert G, Suastegui J (1984). "Purification, molecular and kinetic properties of glucosamine-6-phosphate isomerase (deaminase) from Escherichia coli." Biochim Biophys Acta 1984;787(2);165-73. PMID: 6375729

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

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

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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