2.0 2012-10-10 12:22:38 -0600 2015-10-15 16:14:24 -0600 ECMDB23220 M2MDB003610 1,6-Anhydro-N-acetyl-beta-muramate 1,6-Anhydro-N-acetyl-beta-muramate monocarboxylic a obtained by removal of a proton from the carboxy group of 1,6-anhydro-N-acetyl-beta-muramic acid. It is a substrate of the enzyme anhydro-N-acetylmuramic acid kinase. The reaction it catalyzes is: ATP + 1,6-anhydro-N-acetyl-beta-muramate + H2O = ADP + N-acetylmuramate 6-phosphate. This enzyme, along with EC 4.2.1.126 (N-acetylmuramic acid 6-phosphate etherase) is required for the utilization of anhydro-N-acetylmuramic acid in proteobacteria. The substrate is either imported from the medium or derived from the bacterium's own cell wall murein during cell wall recycling. The product N-acetylmuramate 6-phosphate is produced as a 7:1 mixture of the α- and β-anomers. (2R)-2-(1R,2S,3R,4R,5R)-4-acetamido-2-Hydroxy-6,8-dioxabicyclo3.2.1octan-3-yloxypropanoate (2R)-2-(1R,2S,3R,4R,5R)-4-acetamido-2-hydroxy-6,8-dioxabicyclo3.2.1octan-3-yloxypropanoic acid (2R)-2-{(1R,2S,3R,4R,5R)-4-(acetylamino)-2-hydroxy-6,8-dioxabicyclo3.2.1oct-3-yloxy}propanoate (2R)-2-{(1R,2S,3R,4R,5R)-4-(acetylamino)-2-hydroxy-6,8-dioxabicyclo3.2.1oct-3-yloxy}propanoic acid (2R)-2-{(1R,2S,3R,4R,5R)-4-acetamido-2-hydroxy-6,8-dioxabicyclo3.2.1oct-3-yloxy}propanoate (non-preferred name) (2R)-2-{(1R,2S,3R,4R,5R)-4-Acetamido-2-hydroxy-6,8-dioxabicyclo3.2.1oct-3-yloxy}propanoic acid (non-preferred name) 1,6-anhMurNAc 1,6-anhydro-N-Acetyl-b-muramate 1,6-anhydro-N-Acetyl-b-muramic acid 1,6-anhydro-N-Acetyl-beta-muramic acid 1,6-anhydro-N-Acetyl-muramate 1,6-anhydro-N-acetyl-muramic acid 1,6-anhydro-N-Acetyl-β-muramate 1,6-anhydro-N-Acetyl-β-muramic acid 1,6-anhydro-N-Acetylmuramate 1,6-anhydro-N-acetylmuramic acid 2-(2-acetylamino-4-HYDROXY-6,8-dioxa-bicyclo3.2.1oct-3-yloxy)-propionate 2-(2-ACETYLAMINO-4-HYDROXY-6,8-DIOXA-BICYCLO3.2.1OCT-3-YLOXY)-PROPIONIC ACID C11H16NO7 274.2472 274.092676871 (2R)-2-{[(1R,2S,3R,4R,5R)-4-acetamido-2-hydroxy-6,8-dioxabicyclo[3.2.1]octan-3-yl]oxy}propanoic acid 1,6-anhMurNAc C[C@@H](O[C@H]1[C@H](O)[C@H]2CO[C@H](O2)[C@@H]1N=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)/p-1/t4-,6-,7-,8-,9-,11-/m1/s1 ZFEGYUMHFZOYIY-YVNCZSHWSA-M logp -1.02 ALOGPS logs -0.25 ALOGPS solubility 1.55e+02 g/l ALOGPS logp -1.4 ChemAxon pka_strongest_acidic 3.56 ChemAxon pka_strongest_basic -0.78 ChemAxon iupac (2R)-2-{[(1R,2S,3R,4R,5R)-4-acetamido-2-hydroxy-6,8-dioxabicyclo[3.2.1]octan-3-yl]oxy}propanoic acid ChemAxon average_mass 274.2472 ChemAxon mono_mass 274.092676871 ChemAxon smiles C[C@@H](O[C@H]1[C@H](O)[C@H]2CO[C@H](O2)[C@@H]1N=C(C)[O-])C(O)=O ChemAxon formula C11H16NO7 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)/p-1/t4-,6-,7-,8-,9-,11-/m1/s1 ChemAxon inchikey ZFEGYUMHFZOYIY-YVNCZSHWSA-M ChemAxon polar_surface_area 114.32 ChemAxon refractivity 58.84 ChemAxon polarizability 25.32 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 7 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 23348 Specdb::MsMs 23349 Specdb::MsMs 23350 Specdb::MsMs 30146 Specdb::MsMs 30147 Specdb::MsMs 30148 C19769 AH0 Anhydro-N-acetylmuramic acid kinase P77570 ANMK_ECOLI anmK http://ecmdb.ca/proteins/P77570.xml Adenosine triphosphate + 1,6-Anhydro-N-acetyl-beta-muramate + Water > ADP + N-Acetylmuramic acid 6-phosphate Adenosine triphosphate + 1,6-Anhydro-N-acetyl-beta-muramate + Water <> ADP + N-Acetylmuramic acid 6-phosphate R09640