2.0 2012-05-31 14:48:41 -0600 2015-06-03 17:20:08 -0600 ECMDB20519 M2MDB001327 1,6-Anhydro-N-acetylmuramate 1,6-anhMurNAC is an Amino Sugar. These are compounds having one alcoholic hydroxy group replaced by an amino group; systematically known as x-amino-x-deoxymonosaccharides. 1,6-anhydro-N-acetylmuramic acid (anhMurNAc) is one of the components of murein that is recycled inside the cell. Although exogenously provided anhMurNAc can be taken up by E. coli, it can not serve as the sole source of carbon for growth. 1,6-anhMurNAc 1,6-Anhydro-N-acetylmuramate 1,6-Anhydro-N-acetylmuramic acid C11H17NO7 275.2552 275.100501903 2-{[(1R,2S,3R,4R)-2-hydroxy-4-[(1-hydroxyethylidene)amino]-6,8-dioxabicyclo[3.2.1]octan-3-yl]oxy}propanoic acid 2-{[(1R,2S,3R,4R)-2-hydroxy-4-[(1-hydroxyethylidene)amino]-6,8-dioxabicyclo[3.2.1]octan-3-yl]oxy}propanoic acid [H]C(C)(O[C@@]1([H])[C@]([H])(O)[C@@]2([H])COC([H])(O2)[C@]1([H])N=C(C)O)C(O)=O InChI=1S/C11H17NO7/c1-4(10(15)16)18-9-7(12-5(2)13)11-17-3-6(19-11)8(9)14/h4,6-9,11,14H,3H2,1-2H3,(H,12,13)(H,15,16)/t4?,6-,7-,8-,9-,11?/m1/s1 ZFEGYUMHFZOYIY-NFSFVEDMSA-N Cytoplasm Periplasm logp -0.62 ALOGPS logs -0.78 ALOGPS solubility 4.54e+01 g/l ALOGPS logp -0.55 ChemAxon pka_strongest_acidic 3.54 ChemAxon pka_strongest_basic 1.36 ChemAxon iupac 2-{[(1R,2S,3R,4R)-2-hydroxy-4-[(1-hydroxyethylidene)amino]-6,8-dioxabicyclo[3.2.1]octan-3-yl]oxy}propanoic acid ChemAxon average_mass 275.2552 ChemAxon mono_mass 275.100501903 ChemAxon smiles [H]C(C)(O[C@@]1([H])[C@]([H])(O)[C@@]2([H])COC([H])(O2)[C@]1([H])N=C(C)O)C(O)=O ChemAxon formula C11H17NO7 ChemAxon inchi InChI=1S/C11H17NO7/c1-4(10(15)16)18-9-7(12-5(2)13)11-17-3-6(19-11)8(9)14/h4,6-9,11,14H,3H2,1-2H3,(H,12,13)(H,15,16)/t4?,6-,7-,8-,9-,11?/m1/s1 ChemAxon inchikey ZFEGYUMHFZOYIY-NFSFVEDMSA-N ChemAxon polar_surface_area 117.81 ChemAxon refractivity 59.37 ChemAxon polarizability 25.7 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 8 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon 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 1,6-anhydro-N-acetylmuramic acid recycling PWY0-1261 Specdb::CMs 1085434 Specdb::EiMs 2123 Specdb::NmrOneD 274998 Specdb::NmrOneD 274999 Specdb::NmrOneD 275000 Specdb::NmrOneD 275001 Specdb::NmrOneD 275002 Specdb::NmrOneD 275003 Specdb::NmrOneD 275004 Specdb::NmrOneD 275005 Specdb::NmrOneD 275006 Specdb::NmrOneD 275007 Specdb::NmrOneD 275008 Specdb::NmrOneD 275009 Specdb::NmrOneD 275010 Specdb::NmrOneD 275011 Specdb::NmrOneD 275012 Specdb::NmrOneD 275013 Specdb::NmrOneD 275014 Specdb::NmrOneD 275015 Specdb::NmrOneD 275016 Specdb::NmrOneD 275017 Specdb::MsMs 25103 Specdb::MsMs 25104 Specdb::MsMs 25105 Specdb::MsMs 31661 Specdb::MsMs 31662 Specdb::MsMs 31663 25201515 40666 CPD0-882 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 Beta-hexosaminidase P75949 NAGZ_ECOLI nagZ http://ecmdb.ca/proteins/P75949.xml Anhydro-N-acetylmuramic acid kinase P77570 ANMK_ECOLI anmK http://ecmdb.ca/proteins/P77570.xml 1,6-anhydro-N-acetylmuramyl-L-alanine amidase AmpD P13016 AMPD_ECOLI ampD http://ecmdb.ca/proteins/P13016.xml 1,6-Anhydrous-N-Acetylmuramyl-tetrapeptide + Water > L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine + 1,6-Anhydro-N-acetylmuramate 1,6-Anhydrous-N-Acetylmuramyl-tripeptide + Water > L-alanine-D-glutamate-meso-2,6-diaminoheptanedioate + 1,6-Anhydro-N-acetylmuramate N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramic acid + Water > N-Acetyl-D-glucosamine + 1,6-Anhydro-N-acetylmuramate 1,6-Anhydro-N-acetylmuramate + Adenosine triphosphate + Water > N-Acetylmuramic acid 6-phosphate + ADP + Hydrogen ion RXN0-4621 N-acetyl-β-D-glucosamine(anhydrous)-N-acetylmuramate + Water N-Acetyl-D-glucosamine + 1,6-Anhydro-N-acetylmuramate RXN0-5226 Adenosine triphosphate + Water + 1,6-Anhydro-N-acetylmuramate <> Adenosine diphosphate + MurNAc-6-P + ADP PW_R005315