2.0 2012-05-31 13:44:21 -0600 2015-06-03 15:53:41 -0600 ECMDB01062 M2MDB000238 N-Acetyl-D-Glucosamine 6-Phosphate N-Acetyl-D-Glucosamine 6-Phosphate is an intermediate in the metabolism of Aminosugars. It is a substrate for Glucosamine 6-phosphate N-acetyltransferase. N-acetyl-D-glucosamine-6-P N-acetyl-glucosamine-6-P N-acetyl-glucosamine-6-phosphate N-acetylglucosamine-6-P GlcNAc-6-P N-Acetyl-D-Glucosamine 6-Phosphate N-Acetyl-D-glucosamine 6-phosphoric acid N-Acetyl-D-glucosamine-6-p N-Acetyl-D-glucosamine-6-phosphate N-Acetyl-D-glucosamine-6-phosphoric acid N-Acetyl-glucosamine-6-p N-Acetyl-glucosamine-6-phosphate n-Acetyl-glucosamine-6-phosphoric acid N-Acetyl-glucosamine-6-phosphoric acid N-Acetylglucosamine-6-p NAcGlcNP C8H16NO9P 301.1877 301.056267627 {[(2R,3S,4R,5R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid [(2R,3S,4R,5R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxyphosphonic acid 102029-88-9 CC(=O)N[C@H]1C(O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O 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)/t4-,5-,6-,7-,8?/m1/s1 BRGMHAYQAZFZDJ-RTRLPJTCSA-N Solid Cytosol logp -2.02 ALOGPS logs -1.23 ALOGPS solubility 1.76e+01 g/l ALOGPS logp -3.3 ChemAxon pka_strongest_acidic 1.23 ChemAxon pka_strongest_basic -0.79 ChemAxon iupac {[(2R,3S,4R,5R)-5-acetamido-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid ChemAxon average_mass 301.1877 ChemAxon mono_mass 301.056267627 ChemAxon smiles CC(=O)N[C@H]1C(O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O ChemAxon formula C8H16NO9P ChemAxon 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)/t4-,5-,6-,7-,8?/m1/s1 ChemAxon inchikey BRGMHAYQAZFZDJ-RTRLPJTCSA-N ChemAxon polar_surface_area 165.78 ChemAxon refractivity 57.9 ChemAxon polarizability 25.8 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 8 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Galactose metabolism Galactose can be synthesized through two pathways: melibiose degradation involving an alpha galactosidase and lactose degradation involving a beta galactosidase. Melibiose is first transported inside the cell through the melibiose:Li+/Na+/H+ symporter. Once inside the cell, melibiose is degraded through alpha galactosidase into an alpha-D-galactose and a beta-D-glucose. The beta-D-glucose is phosphorylated by a glucokinase to produce a beta-D-glucose-6-phosphate which can spontaneously be turned into a alpha D glucose 6 phosphate. This alpha D-glucose-6-phosphate is metabolized into a glucose -1-phosphate through a phosphoglucomutase-1. The glucose -1-phosphate is transformed into a uridine diphosphate glucose through UTP--glucose-1-phosphate uridylyltransferase. The product, uridine diphosphate glucose, can undergo a reversible reaction in which it can be turned into uridine diphosphategalactose through an UDP-glucose 4-epimerase. Galactose can also be produced by lactose degradation involving a lactose permease to uptake lactose from the environment and a beta-galactosidase to turn lactose into Beta-D-galactose. Beta-D-galactose can also be uptaken from the environment through a galactose proton symporter. Galactose is degraded through the following process: Beta-D-galactose is introduced into the cytoplasm through a galactose proton symporter, or it can be synthesized from an alpha lactose that is introduced into the cytoplasm through a lactose permease. Alpha lactose interacts with water through a beta-galactosidase resulting in a beta-D-glucose and beta-D-galactose. Beta-D-galactose is isomerized into D-galactose. D-Galactose undergoes phosphorylation through a galactokinase, hence producing galactose 1 phosphate. On the other side of the pathway, a gluose-1-phosphate (product of the interaction of alpha-D-glucose 6-phosphate with a phosphoglucomutase resulting in a alpha-D-glucose-1-phosphate, an isomer of Glucose 1-phosphate, or an isomer of Beta-D-glucose 1-phosphate) interacts with UTP and a hydrogen ion in order to produce a uridine diphosphate glucose. This is followed by the interaction of galactose-1-phosphate with an established amount of uridine diphosphate glucose through a galactose-1-phosphate uridylyltransferase, which in turn output a glucose-1-phosphate and a uridine diphosphate galactose. The glucose -1-phosphate is transformed into a uridine diphosphate glucose through UTP--glucose-1-phosphate uridylyltransferase. The product, uridine diphosphate glucose, can undergo a reversible reaction in which it can be turned into uridine diphosphategalactose through an UDP-glucose 4-epimerase, and so the cycle can keep going as long as more lactose or galactose is imported into the cell PW000821 ec00052 Metabolic Amino sugar and nucleotide sugar metabolism ec00520 Phosphotransferase system (PTS) ec02060 Amino sugar and nucleotide sugar metabolism I The synthesis of amino sugars and nucleotide sugars starts with the phosphorylation of N-Acetylmuramic acid (MurNac) through its transport from the periplasmic space to the cytoplasm. Once in the cytoplasm, MurNac and water undergo a reversible reaction through a N-acetylmuramic acid 6-phosphate etherase, producing a D-lactic acid and N-Acetyl-D-Glucosamine 6-phosphate. This latter compound can also be introduced into the cytoplasm through a phosphorylating PTS permase in the inner membrane that allows for the transport of N-Acetyl-D-glucosamine from the periplasmic space. N-Acetyl-D-Glucosamine 6-phosphate can also be obtained from chitin dependent reactions. Chitin is hydrated through a bifunctional chitinase to produce chitobiose. This in turn gets hydrated by a beta-hexosaminidase to produce N-acetyl-D-glucosamine. The latter undergoes an atp dependent phosphorylation leading to the production of N-Acetyl-D-Glucosamine 6-phosphate. N-Acetyl-D-Glucosamine 6-phosphate is then be deacetylated in order to produce Glucosamine 6-phosphate through a N-acetylglucosamine-6-phosphate deacetylase. This compound can either be isomerized or deaminated into Beta-D-fructofuranose 6-phosphate through a glucosamine-fructose-6-phosphate aminotransferase and a glucosamine-6-phosphate deaminase respectively. Glucosamine 6-phosphate undergoes a reversible reaction to glucosamine 1 phosphate through a phosphoglucosamine mutase. This compound is then acetylated through a bifunctional protein glmU to produce a N-Acetyl glucosamine 1-phosphate. N-Acetyl glucosamine 1-phosphate enters the nucleotide sugar synthesis by reacting with UTP and hydrogen ion through a bifunctional protein glmU releasing pyrophosphate and a Uridine diphosphate-N-acetylglucosamine.This compound can either be isomerized into a UDP-N-acetyl-D-mannosamine or undergo a reaction with phosphoenolpyruvic acid through UDP-N-acetylglucosamine 1-carboxyvinyltransferase releasing a phosphate and a UDP-N-Acetyl-alpha-D-glucosamine-enolpyruvate. UDP-N-acetyl-D-mannosamine undergoes a NAD dependent dehydrogenation through a UDP-N-acetyl-D-mannosamine dehydrogenase, releasing NADH, a hydrogen ion and a UDP-N-Acetyl-alpha-D-mannosaminuronate, This compound is then used in the production of enterobacterial common antigens. UDP-N-Acetyl-alpha-D-glucosamine-enolpyruvate is reduced through a NADPH dependent UDP-N-acetylenolpyruvoylglucosamine reductase, releasing a NADP and a UDP-N-acetyl-alpha-D-muramate. This compound is involved in the D-glutamine and D-glutamate metabolism. PW000886 Metabolic Amino sugar and nucleotide sugar metabolism II The synthesis of amino sugars and nucleotide sugars starts with the phosphorylation of N-Acetylmuramic acid (MurNac) through its transport from the periplasmic space to the cytoplasm. Once in the cytoplasm, MurNac and water undergo a reversible reaction through a N-acetylmuramic acid 6-phosphate etherase, producing a D-lactic acid and N-Acetyl-D-Glucosamine 6-phosphate. This latter compound can also be introduced into the cytoplasm through a phosphorylating PTS permase in the inner membrane that allows for the transport of N-Acetyl-D-glucosamine from the periplasmic space. N-Acetyl-D-Glucosamine 6-phosphate can also be obtained from chitin dependent reactions. Chitin is hydrated through a bifunctional chitinase to produce chitobiose. This in turn gets hydrated by a beta-hexosaminidase to produce N-acetyl-D-glucosamine. The latter undergoes an atp dependent phosphorylation leading to the production of N-Acetyl-D-Glucosamine 6-phosphate. N-Acetyl-D-Glucosamine 6-phosphate is then be deacetylated in order to produce Glucosamine 6-phosphate through a N-acetylglucosamine-6-phosphate deacetylase. This compound is then deaminased into Beta-D-fructofuranose 6-phosphate through a glucosamine-6-phosphate deaminase. The beta-D-fructofuranose 6 -phosphate is isomerized in a reversible reaction into an alpha-D-mannose 6-phosphate. This compound can also be introduced into the cell from the periplasmic space through a mannose PTS permease that phosphorylates an alpha-D-mannose. Alpha-D-mannose 6-phosphate undergoes a reversible reaction through a phosphomannomutase to produce an alpha-D-mannose 1-phosphate. The alpha-D-mannose 1-phosphate enters the nucleotide sugar metabolism through a reaction with GTP producing a GDP-mannose and releasing a pyrophosphate, all through a mannose-1-phosphate guanylyltransferase. GDP-mannose is then dehydrated to produce GDP-4-dehydro-6-deoxy-alpha-D-mannose through a GDP-mannose 4,6-dehydratase. This compound is then used to synthesize GDP-Beta-L-fucose through a NADPH dependent GDP-L-fucose synthase. Alpha-D-glucose is introduced into the cytoplasm through a glucose PTS permease, which phosphorylates the compound in order to produce an alpha-D-glucose 6-phosphate. This compound is then modified through a phosphoglucomutase 1 to yield alpha-D-glucose 1-phosphate. This compound can either be adenylated to produce ADP-glucose or uridylylated to produce galactose 1-phosphate through glucose-1-phosphate adenyllyltransferase and galactose-1-phosphate uridylyltransferase respectively. PW000887 Metabolic Amino sugar and nucleotide sugar metabolism III The synthesis of amino sugars and nucleotide sugars starts with the phosphorylation of N-Acetylmuramic acid (MurNac) through its transport from the periplasmic space to the cytoplasm. Once in the cytoplasm, MurNac and water undergo a reversible reaction through a N-acetylmuramic acid 6-phosphate etherase, producing a D-lactic acid and N-Acetyl-D-Glucosamine 6-phosphate. This latter compound can also be introduced into the cytoplasm through a phosphorylating PTS permase in the inner membrane that allows for the transport of N-Acetyl-D-glucosamine from the periplasmic space. N-Acetyl-D-Glucosamine 6-phosphate can also be obtained from chitin dependent reactions. Chitin is hydrated through a bifunctional chitinase to produce chitobiose. This in turn gets hydrated by a beta-hexosaminidase to produce N-acetyl-D-glucosamine. The latter undergoes an atp dependent phosphorylation leading to the production of N-Acetyl-D-Glucosamine 6-phosphate. N-Acetyl-D-Glucosamine 6-phosphate is then be deacetylated in order to produce Glucosamine 6-phosphate through a N-acetylglucosamine-6-phosphate deacetylase. This compound is then deaminased into Beta-D-fructofuranose 6-phosphate through a glucosamine-6-phosphate deaminase. Beta-D-fructofuranose 6-phosphate is isomerized into a beta-D-glucose 6-phosphate through a glucose-6-phosphate isomerase. The compound is then isomerized by a putative beta-phosphoglucomutase to produce a beta-D-glucose 1-phosphate. This compound enters the nucleotide sugar metabolism through uridylation resulting in a UDP-glucose. UDP-glucose is then dehydrated through a UDP-glucose 6-dehydrogenase to produce a UDP-glucuronic acid. This compound undergoes a NAD dependent reaction through a bifunctional polymyxin resistance protein to produce UDP-Beta-L-threo-pentapyranos-4-ulose. This compound then reacts with L-glutamic acid through a UDP-4-amino-4-deoxy-L-arabinose--oxoglutarate aminotransferase to produce an oxoglutaric acid and UDP-4-amino-4-deoxy-beta-L-arabinopyranose The latter compound interacts with a N10-formyl-tetrahydrofolate through a bifunctional polymyxin resistance protein ArnA, resulting in a tetrahydrofolate, a hydrogen ion and a UDP-4-deoxy-4-formamido-beta-L-arabinopyranose, which in turn reacts with a product of the methylerythritol phosphate and polysoprenoid biosynthesis pathway, di-trans,octa-cis-undecaprenyl phosphate to produce a 4-deoxy-4-formamido-alpha-L-arabinopyranosyl ditrans, octacis-undecaprenyl phosphate. Alpha-D-glucose is introduced into the cytoplasm through a glucose PTS permease, which phosphorylates the compound in order to produce an alpha-D-glucose 6-phosphate. This compound is then modified through a phosphoglucomutase 1 to yield alpha-D-glucose 1-phosphate. This compound can either be adenylated to produce ADP-glucose or uridylylated to produce galactose 1-phosphate through glucose-1-phosphate adenyllyltransferase and galactose-1-phosphate uridylyltransferase respectively. PW000895 Metabolic inner membrane transport list of inner membrane transport complexes, transporting compounds from the periplasmic space to the cytosol This pathway should be updated regularly with the new inner membrae transports added PW000786 Metabolic 1,6-anhydro-N-acetylmuramic acid recycling Anhydromuropeptides (mainly GlcNAc-1,6-anhMurNAc-L-Ala-γ-D-Glu-DAP-D-Ala) are steadily released during growth by lytic transglycosylases and endopeptidases and imported back into the cytoplasm for recycling. During bacterial growth, a very large proportion of the peptidoglycan polymer is degraded and reused in a process termed cell wall recycling. For example, the Gram-negative bacterium Escherichia coli recovers about half of its cell wall within one generation. The anhydromuropeptides are imported by the ampG-encoded muropeptide:H+ symporter. Once inside the cytoplasm, the anhydromuropeptides are hydrolyzed by N-acetylmuramoyl-L-alanine amidase (ampD), β-N-acetylhexosaminidase (nagZ) and L,D-carboxypeptidase A (ldcA), yielding N-acetyl-β-D-glucosamine, 1,6-anhydro-N-acetyl-β-muramate, L-alanyl-γ-D-glutamyl-meso-diaminopimelate and D-alanine. 1,6-anhydro-N-acetyl-β-muramate is phosphorylated by anhydro-N-acetylmuramic acid kinase (anmK) and then converted into N-acetyl-D-glucosamine 6-phosphate by N-acetylmuramic acid 6-phosphate etherase (murQ). This is a branch point, as this compound could be directed either for further degradation or for recycling into new peptidoglycan monomers, as described in this pathway. The final product of this pathway, UDP-N-acetyl-α-D-muramate, is one of the precursors for peptidoglycan biosynthesis. The tripeptide L-alanyl-γ-D-glutamyl-meso-diaminopimelate, which is generated by muramoyltetrapeptide carboxypeptidase, can be degraded further, as described in muropeptide degradation. However, the vast majority is recycled by muropeptide ligase (mpl). This enzyme is a dedicated recycling enzyme that attaches the recovered Ala-Glu-DAP tripeptide to UDP-N-acetyl-α-D-muramate, thereby substituting three amino acid ligases of the peptidoglycan de novobiosynthetic pathway. Although exogenously provided 1,6-anhydro-N-acetyl-β-muramate can be taken up by Escherichia coli, it can not serve as the sole source of carbon for growth, suggesting that it may be toxic to the cell. (EcoCyc) PW002064 Metabolic Chitobiose Degradation The β-glucoside N,N'-diacetylchitobiose is the major breakdown product of chitin, the second most abundant biopolymer after cellulose. E. coli is capable of using N,N'-diacetylchitobiose as the sole source of carbon. Chitobiose is imported and concurrently phosphorylated to N,N'-diacetylchitobiose 6'-phosphate by the chitobiose PTS transporter. Recent evidence suggests that this is followed by deacetylation of the unphosphorylated acetylglucosamine moiety at the reducing end of N,N'-diacetylchitobiose 6'-phosphate by chito-oligosaccharide mono-deacetylase. N-monoacetylchitobiose 6'-phosphate is subsequently hydrolyzed by the glycosyl hydrolase monoacetylchitobiose-6-phosphate hydrolase to D-glucosamine and N-acetyl-D-glucosamine 6-phosphate. N-acetyl-D-glucosamine 6-phosphate enters the N-acetylglucosamine degradation I pathway for conversion to β-D-fructofuranose 6-phosphate, which enters glycolysis. The fate of D-glucosamine is currently unclear; when used as a carbon source, D-glucosamine enters the cell via a PTS transporter and is thereby phosphorylated. It is possible that an intracellular D-glucosamine kinase activity enables utilization of this compound. (EcoCyc) PW002042 Metabolic N-acetylneuraminate and N-acetylmannosamine and N-acetylglucosamine degradation The degradation of N-acetylneuraminate begins with its incorporation into the cytosol through a hydrogen symporter. Once inside the cytosol it is degraded by a N-acetylneuraminate lyase resulting in a release of a pyruvic acid and N-acetymannosamine. The latter compound is phosphorylated by an ATP driven N-Acetylmannosamine kinase resulting in the release of an ADP, a hydrogen ion and a N-Acetyl-D-mannosamine 6-phosphate. This phosphorylated compound is then metabolized by a putative N-acetylmannosamine-6-phosphate 2-epimerase resulting in the release of a N-Acetyl-D-glucosamine 6-phosphate. This compound is then deacetylated through a N-acetylglucosamine-6-phosphate deacetylase resulting in the release of an Acetic acid and a glucosamine 6-phosphate This compound can then be deaminated through a glucosamine-6-phosphate deaminase resulting in the release of an ammonium and a beta-D-fructofuranose 6-phosphate which can then be incorporated into the glycolysis pathway. PW002030 Metabolic N-acetylglucosamine degradation I GLUAMCAT-PWY chitobiose degradation PWY0-1309 N-acetylneuraminate and N-acetylmannosamine degradation PWY0-1324 1,6-anhydro-N-acetylmuramic acid recycling PWY0-1261 Specdb::CMs 3427 Specdb::CMs 30632 Specdb::CMs 30633 Specdb::CMs 37910 Specdb::CMs 99647 Specdb::CMs 99648 Specdb::CMs 149846 Specdb::NmrOneD 8502 Specdb::NmrOneD 8503 Specdb::NmrOneD 8504 Specdb::NmrOneD 8505 Specdb::NmrOneD 8506 Specdb::NmrOneD 8507 Specdb::NmrOneD 8508 Specdb::NmrOneD 8509 Specdb::NmrOneD 8510 Specdb::NmrOneD 8511 Specdb::NmrOneD 8512 Specdb::NmrOneD 8513 Specdb::NmrOneD 8514 Specdb::NmrOneD 8515 Specdb::NmrOneD 8516 Specdb::NmrOneD 8517 Specdb::NmrOneD 8518 Specdb::NmrOneD 8519 Specdb::NmrOneD 8520 Specdb::NmrOneD 8521 Specdb::MsMs 26471 Specdb::MsMs 26472 Specdb::MsMs 26473 Specdb::MsMs 33029 Specdb::MsMs 33030 Specdb::MsMs 33031 Specdb::MsMs 437264 Specdb::MsMs 437265 Specdb::MsMs 437266 Specdb::MsMs 437267 Specdb::MsMs 437268 Specdb::MsMs 2402849 Specdb::MsMs 2402850 Specdb::MsMs 2402851 Specdb::MsMs 2533341 Specdb::MsMs 2533342 Specdb::MsMs 2533343 HMDB01062 440996 389821 C00357 15784 N-ACETYL-D-GLUCOSAMINE-6-P Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 Komatsuzawa H, Fujiwara T, Nishi H, Yamada S, Ohara M, McCallum N, Berger-Bachi B, Sugai M: The gate controlling cell wall synthesis in Staphylococcus aureus. Mol Microbiol. 2004 Aug;53(4):1221-31. 15306023 Phosphoenolpyruvate-protein phosphotransferase P08839 PT1_ECOLI ptsI http://ecmdb.ca/proteins/P08839.xml PTS system N-acetylglucosamine-specific EIICBA component P09323 PTW3C_ECOLI nagE http://ecmdb.ca/proteins/P09323.xml Putative N-acetylmannosamine-6-phosphate 2-epimerase P0A761 NANE_ECOLI nanE http://ecmdb.ca/proteins/P0A761.xml N-acetylglucosamine-6-phosphate deacetylase P0AF18 NAGA_ECOLI nagA http://ecmdb.ca/proteins/P0AF18.xml 6-phospho-beta-glucosidase P17411 CHBF_ECOLI chbF http://ecmdb.ca/proteins/P17411.xml Glucose-specific phosphotransferase enzyme IIA component P69783 PTGA_ECOLI crr http://ecmdb.ca/proteins/P69783.xml PTS system glucose-specific EIICB component P69786 PTGCB_ECOLI ptsG http://ecmdb.ca/proteins/P69786.xml N-acetyl-D-glucosamine kinase P75959 NAGK_ECOLI nagK http://ecmdb.ca/proteins/P75959.xml N-acetylmuramic acid 6-phosphate etherase P76535 MURQ_ECOLI murQ http://ecmdb.ca/proteins/P76535.xml Phosphocarrier protein HPr P0AA04 PTHP_ECOLI ptsH http://ecmdb.ca/proteins/P0AA04.xml PTS system N-acetylglucosamine-specific EIICBA component P09323 PTW3C_ECOLI nagE http://ecmdb.ca/proteins/P09323.xml PTS system glucose-specific EIICB component P69786 PTGCB_ECOLI ptsG http://ecmdb.ca/proteins/P69786.xml Phosphoenolpyruvic acid + N-Acetyl-D-glucosamine > N-Acetyl-D-Glucosamine 6-Phosphate + Pyruvic acid TRANS-RXN-167 N-Acetyl-D-Glucosamine 6-Phosphate + Water <> Acetic acid + Glucosamine 6-phosphate R02059 NAG6PDEACET-RXN N-Acetyl-D-glucosamine + Adenosine triphosphate <> N-Acetyl-D-Glucosamine 6-Phosphate + ADP + Hydrogen ion R01201 N-ACETYLGLUCOSAMINE-KINASE-RXN Diacetylchitobiose-6-phosphate + Water > N-Acetyl-D-glucosamine + N-Acetyl-D-Glucosamine 6-Phosphate RXN0-5243 N-Acetylmuramic acid 6-phosphate + Water <> N-Acetyl-D-Glucosamine 6-Phosphate + D-Lactic acid R08555 RXN0-4641 N-Acetyl-D-mannosamine 6-phosphate <> N-Acetyl-D-Glucosamine 6-Phosphate R02087 NANE-RXN Adenosine triphosphate + N-Acetyl-D-glucosamine <> ADP + N-Acetyl-D-Glucosamine 6-Phosphate R01201 N-Acetyl-D-Glucosamine 6-Phosphate <> N-Acetyl-D-mannosamine 6-phosphate R02087 Protein N(pi)-phospho-L-histidine + N-Acetyl-D-glucosamine <> Protein histidine + N-Acetyl-D-Glucosamine 6-Phosphate R05199 N-Acetyl-D-glucosamine + Adenosine triphosphate > Hydrogen ion + N-Acetyl-D-Glucosamine 6-Phosphate + ADP R01201 N-ACETYLGLUCOSAMINE-KINASE-RXN Water + N-Acetyl-D-Glucosamine 6-Phosphate > Glucosamine 6-phosphate + Acetic acid NAG6PDEACET-RXN Phosphoenolpyruvic acid + N-Acetyl-D-glucosamine > N-Acetyl-D-Glucosamine 6-Phosphate + Pyruvic acid TRANS-RXN-167 N-Acetylmuramic acid 6-phosphate + Water > N-Acetyl-D-Glucosamine 6-Phosphate + D-Lactic acid N-Acetyl-D-Glucosamine 6-Phosphate + Water > D-glucosamine 6-phosphate + Acetic acid Adenosine triphosphate + N-Acetylglucosamine > ADP + N-Acetyl-D-Glucosamine 6-Phosphate N-Acetyl-D-Glucosamine 6-Phosphate + Water + N-Acetyl-D-Glucosamine 6-Phosphate > Acetic acid + Glucosamine 6-phosphate PW_R003304 N-Acetyl-D-glucosamine + Adenosine triphosphate + N-Acetylglucosamine > N-Acetyl-D-Glucosamine 6-Phosphate + Adenosine diphosphate + Hydrogen ion + N-Acetyl-D-Glucosamine 6-Phosphate + ADP PW_R003308 N-Acetyl-D-glucosamine + HPr - phosphorylated + N-Acetylglucosamine > N-Acetyl-D-Glucosamine 6-Phosphate + HPr + N-Acetyl-D-Glucosamine 6-Phosphate PW_RCT000127 N'-monoacetylchitobiose-6'-phosphate + Water > N-Acetyl-D-Glucosamine 6-Phosphate + Glucosamine PW_R005988 N-Acetylmuramate 6-phosphate + Water <> N-Acetyl-D-Glucosamine 6-Phosphate + D-Lactic acid PW_R006028