2.0 2012-05-31 13:58:34 -0600 2015-09-13 12:56:12 -0600 ECMDB03339 M2MDB000491 D-Glutamic acid D-glutamate is a key component of peptidoglycan synthesis. The peptidoglycan synthesis pathway starts at the cytoplasm, where in six steps the peptidoglycan precursor a UDP-N-acetylmuramoyl-pentapeptide is synthesized. This precursor is then attached to the memberane acceptor all-trans-undecaprenyl phosphate, generating a N-acetylmuramoyl-pentapeptide-diphosphoundecaprenol, also known as lipid I. Another transferase then adds UDP-N-acetyl-alpha-D-glucosamine, yielding the complete monomeric unit a lipid , also known as lipid . This final lipid intermediate is transferred through the membrane. The peptidoglycan monomers are then polymerized on the outside surface by glycosyltransferases, which form the linear glycan chains, and transpeptidases, which catalyze the formation of peptide crosslinks. There are two forms of glutamic acid found in nature: L-glutamic acid and D-glutamic acid. D-glutamic acid is found naturally primarily in the cell walls of certain bacteria - including E. coli. D-glutamate is also present in certain foods e.g., soybeans and also arises from the turnover of the intestinal tract microflora, whose cell walls contain significant D-glutamate. Unlike other D-amino acids, D-glutamate is not oxidized by the D-amino acid oxidases, and therefore this detoxification pathway is not available for handling D-glutamate. Likewise, D-glutamic acid, when ingested, largely escapes most deamination reactions (unlike the L-counterpart). D-glutamate is the most potent natural inhibitor of glutathione synthesis identified to date. (2R)-2-aminopentanedioate (2R)-2-aminopentanedioic acid (R)-2-aminopentanedioate (R)-2-aminopentanedioic acid D-2-Aminoglutarate D-2-Aminoglutaric acid D-2-Aminopentanedioate D-2-Aminopentanedioic acid D-Glu D-Glutamate D-Glutamic acid D-Glutaminate D-Glutaminic acid D-Glutaminsaeure Delta-2-Aminoglutarate Delta-2-Aminoglutaric acid Delta-2-Aminopentanedioate Delta-2-Aminopentanedioic acid Delta-Glutamate Delta-Glutamic acid Delta-Glutaminate Delta-Glutaminic acid Delta-Glutaminsaeure DGL Glutamate Glutamate D-form Glutamic acid Glutamic acid D-form Lopac-G-2128 Lopac-gamma-2128 Lopac-γ-2128 R-(-)-Glutamate R-(-)-Glutamic acid Tocris-0217 δ-2-Aminoglutarate δ-2-Aminoglutaric acid δ-2-Aminopentanedioate δ-2-Aminopentanedioic acid δ-Glutamate δ-Glutamic acid δ-Glutaminate δ-Glutaminic acid δ-Glutaminsaeure C5H9NO4 147.1293 147.053157781 (2R)-2-aminopentanedioic acid D-glutamic acid 6893-26-1 N[C@H](CCC(O)=O)C(O)=O InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m1/s1 WHUUTDBJXJRKMK-GSVOUGTGSA-N Solid Cytosol logp -3.54 ALOGPS logs -0.26 ALOGPS solubility 8.06e+01 g/l ALOGPS melting_point 201 oC logp -3.2 ChemAxon pka_strongest_acidic 1.88 ChemAxon pka_strongest_basic 9.54 ChemAxon iupac (2R)-2-aminopentanedioic acid ChemAxon average_mass 147.1293 ChemAxon mono_mass 147.053157781 ChemAxon smiles N[C@H](CCC(O)=O)C(O)=O ChemAxon formula C5H9NO4 ChemAxon inchi InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m1/s1 ChemAxon inchikey WHUUTDBJXJRKMK-GSVOUGTGSA-N ChemAxon polar_surface_area 100.62 ChemAxon refractivity 31.29 ChemAxon polarizability 13.19 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 5 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Vitamin B6 metabolism ec00750 Peptidoglycan biosynthesis ec00550 D-Glutamine and D-glutamate metabolism L-glutamine is transported into the cytoplasm through a glutamine ABC transporter. Once inside, L-glutamine is metabolized with glutaminase to produce an L-glutamic acid. This process can be reversed through a glutamine synthetase resulting in L-glutamine. L-glutamic acid can also be transported into the cytoplasm through various methods: a glutamate/aspartate:H+ symporter GltP, a glutamate: sodium symporter or a glutamate/aspartate ABC transporter. L-glutamic acid can proceed to L-glutamate metabolism or it can undergo a reversible reaction through a glutamate racemase resulting in D-glutamic acid. This compound can also be obtained from D-glutamine interacting with a glutaminase. D-glutamic acid reacts with UDP-N-acetylmuramoyl-L-alanine through an ATP driven UDP-N-acetylmuramoylalanine-D-glutamate ligase resulting in a UDP-N-acetylmuramoyl-L-alanyl-D-glutamate which is then integrated into the peptidoglycan biosynthesis UDP-N-acetylmuramoyl-L-alanine comes from the amino sugar and nucleotide sugar metabolism product, UDP-N-acetylmuraminate which reacts with L-alanine through an ATP-driven UDP-N-acetylmuramate-L-alanine ligase. PW000769 ec00471 Metabolic Metabolic pathways eco01100 peptidoglycan biosynthesis I Peptidoglycan is a net-like polymer which surrounds the cytoplasmic membrane of most bacteria and functions to maintain cell shape and prevent rupture due to the internal turgor.In E. coli K-12, the peptidoglycan consists of glycan strands of alternating subunits of N-acetylglucosamine (GlcNAc) and N-acetylmuramic acid (MurNAc) which are cross-linked by short peptides. The pathway for constructing this net involves two cell compartments: cytoplasm and periplasmic space. The pathway starts with a beta-D-fructofuranose going through a mannose PTS permease, phosphorylating the compund and producing a beta-D-fructofuranose 6 phosphate. This compound can be obtained from the glycolysis and pyruvate dehydrogenase or from an isomerization reaction of Beta-D-glucose 6-phosphate through a glucose-6-phosphate isomerase.The compound Beta-D-fructofuranose 6 phosphate and L-Glutamine react with a glucosamine fructose-6-phosphate aminotransferase, thus producing a glucosamine 6-phosphate and a l-glutamic acid. The glucosamine 6-phosphate interacts with phosphoglucosamine mutase in a reversible reaction producing glucosamine-1P. Glucosamine-1p and acetyl coa undergo acetylation throuhg a bifunctional protein glmU releasing Coa and a hydrogen ion and producing a N-acetyl-glucosamine 1-phosphate. Glmu, being a bifunctional protein, follows catalyze the interaction of N-acetyl-glucosamine 1-phosphate, hydrogen ion and UTP into UDP-N-acetylglucosamine and pyrophosphate. UDP-N-acetylglucosamine then interacts with phosphoenolpyruvic acid and a UDP-N acetylglucosamine 1- carboxyvinyltransferase realeasing a phosphate and the compound UDP-N-acetyl-alpha-D-glucosamine-enolpyruvate. This compound undergoes a NADPH dependent reduction producing a UDP-N-acetyl-alpha-D-muramate through a UDP-N-acetylenolpyruvoylglucosamine reductase. UDP-N-acetyl-alpha-D-muramate and L-alanine react in an ATP-mediated ligation through a UDP-N-acetylmuramate-alanine ligase releasing an ADP, hydrogen ion, a phosphate and a UDP-N-acetylmuramoyl-L-alanine. This compound interacts with D-glutamic acid and ATP through UDP-N-acetylmuramoylalanine-D-glutamate ligase releasing ADP, A phosphate and UDP-N-acetylmuramoyl-L-alanyl-D-glutamate. The latter compound then interacts with meso-diaminopimelate in an ATP mediated ligation through a UDP-N-acetylmuramoylalanine-D-glutamate-2,6-diaminopimelate ligase resulting in ADP, phosphate, hydrogen ion and UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate. This compound in turn with D-alanyl-D-alanine react in an ATP-mediated ligation through UDP-N-Acetylmuramoyl-tripeptide-D-alanyl-D-alanine ligase to produce UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-gama-D-glutamyl-meso-2,6-diaminopimeloyl-Dalanyl-D-alanine and hydrogen ion, ADP, phosphate. UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-gama-D-glutamyl-meso-2,6-diaminopimeloyl-Dalanyl-D-alanine interacts with di-trans,octa-cis-undecaprenyl phosphate through a phospho-N-acetylmuramoyl-pentapeptide-transferase, resulting in UMP and Undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine which in turn reacts with a UDP-N-acetylglucosamine through a N-acetylglucosaminyl transferase to produce a hydrogen, UDP and ditrans,octacis-undecaprenyldiphospho-N-acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-gamma-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine. This compound ends the cytoplasmic part of the pathway. ditrans,octacis-undecaprenyldiphospho-N-acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-gamma-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine is transported through a lipi II flippase. Once in the periplasmic space, the compound reacts with a penicillin binding protein 1A prodducing a peptidoglycan dimer, a hydrogen ion, and UDP. The peptidoglycan dimer then reacts with a penicillin binding protein 1B producing a peptidoglycan with D,D, cross-links and a D-alanine. PW000906 Metabolic peptidoglycan biosynthesis I 2 Peptidoglycan is a net-like polymer which surrounds the cytoplasmic membrane of most bacteria and functions to maintain cell shape and prevent rupture due to the internal turgor.In E. coli K-12, the peptidoglycan consists of glycan strands of alternating subunits of N-acetylglucosamine (GlcNAc) and N-acetylmuramic acid (MurNAc) which are cross-linked by short peptides. The pathway for constructing this net involves two cell compartments: cytoplasm and periplasmic space. The pathway starts with a beta-D-fructofuranose going through a mannose PTS permease, phosphorylating the compund and producing a beta-D-fructofuranose 6 phosphate. This compound can be obtained from the glycolysis and pyruvate dehydrogenase or from an isomerization reaction of Beta-D-glucose 6-phosphate through a glucose-6-phosphate isomerase.The compound Beta-D-fructofuranose 6 phosphate and L-Glutamine react with a glucosamine fructose-6-phosphate aminotransferase, thus producing a glucosamine 6-phosphate and a l-glutamic acid. The glucosamine 6-phosphate interacts with phosphoglucosamine mutase in a reversible reaction producing glucosamine-1P. Glucosamine-1p and acetyl coa undergo acetylation throuhg a bifunctional protein glmU releasing Coa and a hydrogen ion and producing a N-acetyl-glucosamine 1-phosphate. Glmu, being a bifunctional protein, follows catalyze the interaction of N-acetyl-glucosamine 1-phosphate, hydrogen ion and UTP into UDP-N-acetylglucosamine and pyrophosphate. UDP-N-acetylglucosamine then interacts with phosphoenolpyruvic acid and a UDP-N acetylglucosamine 1- carboxyvinyltransferase realeasing a phosphate and the compound UDP-N-acetyl-alpha-D-glucosamine-enolpyruvate. This compound undergoes a NADPH dependent reduction producing a UDP-N-acetyl-alpha-D-muramate through a UDP-N-acetylenolpyruvoylglucosamine reductase. UDP-N-acetyl-alpha-D-muramate and L-alanine react in an ATP-mediated ligation through a UDP-N-acetylmuramate-alanine ligase releasing an ADP, hydrogen ion, a phosphate and a UDP-N-acetylmuramoyl-L-alanine. This compound interacts with D-glutamic acid and ATP through UDP-N-acetylmuramoylalanine-D-glutamate ligase releasing ADP, A phosphate and UDP-N-acetylmuramoyl-L-alanyl-D-glutamate. The latter compound then interacts with meso-diaminopimelate in an ATP mediated ligation through a UDP-N-acetylmuramoylalanine-D-glutamate-2,6-diaminopimelate ligase resulting in ADP, phosphate, hydrogen ion and UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate. This compound in turn with D-alanyl-D-alanine react in an ATP-mediated ligation through UDP-N-Acetylmuramoyl-tripeptide-D-alanyl-D-alanine ligase to produce UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-gama-D-glutamyl-meso-2,6-diaminopimeloyl-Dalanyl-D-alanine and hydrogen ion, ADP, phosphate. UDP-N-acetyl-alpha-D-muramoyl-L-alanyl-gama-D-glutamyl-meso-2,6-diaminopimeloyl-Dalanyl-D-alanine interacts with di-trans,octa-cis-undecaprenyl phosphate through a phospho-N-acetylmuramoyl-pentapeptide-transferase, resulting in UMP and N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimelyl-D-alanyl-D-alanine-diphosphoundecaprenol which in turn reacts with a UDP-N-acetylglucosamine through a N-acetylglucosaminyl transferase to produce a hydrogen, UDP and Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-D-glutaminyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine. This compound ends the cytoplasmic part of the pathway. Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-D-glutaminyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine is transported through a lipi II flippase. Once in the periplasmic space, the compound reacts with a penicillin binding protein 1A prodducing a peptidoglycan dimer, a hydrogen ion, and UDP. The peptidoglycan dimer then reacts with a penicillin binding protein 1B producing a peptidoglycan with D,D, cross-links and a D-alanine. PW002062 Metabolic UDP-<i>N</i>-acetylmuramoyl-pentapeptide biosynthesis III (<i>meso</i>-DAP-containing) PWY-6387 Specdb::CMs 9441 Specdb::CMs 38576 Specdb::CMs 137814 Specdb::CMs 145548 Specdb::NmrOneD 135650 Specdb::NmrOneD 135651 Specdb::NmrOneD 135652 Specdb::NmrOneD 135653 Specdb::NmrOneD 135654 Specdb::NmrOneD 135655 Specdb::NmrOneD 135656 Specdb::NmrOneD 135657 Specdb::NmrOneD 135658 Specdb::NmrOneD 135659 Specdb::NmrOneD 135660 Specdb::NmrOneD 135661 Specdb::NmrOneD 135662 Specdb::NmrOneD 135663 Specdb::NmrOneD 135664 Specdb::NmrOneD 135665 Specdb::NmrOneD 135666 Specdb::NmrOneD 135667 Specdb::NmrOneD 135668 Specdb::NmrOneD 135669 Specdb::MsMs 25412 Specdb::MsMs 25413 Specdb::MsMs 25414 Specdb::MsMs 31970 Specdb::MsMs 31971 Specdb::MsMs 31972 Specdb::MsMs 437667 Specdb::MsMs 437668 Specdb::MsMs 437669 Specdb::MsMs 437670 Specdb::MsMs 437671 Specdb::MsMs 446166 Specdb::MsMs 446167 Specdb::MsMs 446168 Specdb::MsMs 446169 Specdb::MsMs 446170 Specdb::MsMs 2821188 Specdb::MsMs 2821189 Specdb::MsMs 2821190 Specdb::MsMs 2857002 Specdb::MsMs 2857003 Specdb::MsMs 2857004 HMDB03339 23327 21814 C00217 15966 D-GLT FGA DGL Keseler, I. 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Kokai Tokkyo Koho (1990), 4 pp. http://hmdb.ca/system/metabolites/msds/000/002/920/original/HMDB03339.pdf?1358894045 Glutaminase 2 P0A6W0 GLSA2_ECOLI glsA2 http://ecmdb.ca/proteins/P0A6W0.xml UDP-N-acetylmuramoylalanine--D-glutamate ligase P14900 MURD_ECOLI murD http://ecmdb.ca/proteins/P14900.xml Glutamate racemase P22634 MURI_ECOLI murI http://ecmdb.ca/proteins/P22634.xml Glutaminase 1 P77454 GLSA1_ECOLI glsA1 http://ecmdb.ca/proteins/P77454.xml Glutamate/aspartate transport system permease protein gltJ P0AER3 GLTJ_ECOLI gltJ http://ecmdb.ca/proteins/P0AER3.xml Glutamate/aspartate transport system permease protein gltK P0AER5 GLTK_ECOLI gltK http://ecmdb.ca/proteins/P0AER5.xml Uncharacterized amino-acid ABC transporter ATP-binding protein yecC P37774 YECC_ECOLI yecC http://ecmdb.ca/proteins/P37774.xml Inner membrane amino-acid ABC transporter permease protein yecS P0AFT2 YECS_ECOLI yecS http://ecmdb.ca/proteins/P0AFT2.xml Glutamate/aspartate transport system permease protein gltJ P0AER3 GLTJ_ECOLI gltJ http://ecmdb.ca/proteins/P0AER3.xml Glutamate/aspartate transport system permease protein gltK P0AER5 GLTK_ECOLI gltK http://ecmdb.ca/proteins/P0AER5.xml Sodium/glutamate symport carrier protein P0AER8 GLTS_ECOLI gltS http://ecmdb.ca/proteins/P0AER8.xml Adenosine triphosphate + D-Glutamic acid + UDP-N-Acetylmuramoyl-L-alanine <> ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate R02783 UDP-NACMURALA-GLU-LIG-RXN D-Glutamic acid <> L-Glutamate R00260 GLUTRACE-RXN L-Glutamate <> D-Glutamic acid R00260 GLUTRACE-RXN D-Glutamine + Water <> D-Glutamic acid + Ammonia R01579 Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanine + D-Glutamic acid <> ADP + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate R02783 Pyridoxamine 5'-phosphate + Oxoglutaric acid <> Pyridoxal 5'-phosphate + D-Glutamic acid PYRDAMPTRANS-RXN D-Glutamic acid + UDP-N-Acetylmuramoyl-L-alanine + Adenosine triphosphate > Hydrogen ion + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate + Phosphate + ADP UDP-NACMURALA-GLU-LIG-RXN L-Glutamate > D-Glutamic acid D-Glutamine + Water > D-Glutamic acid + Ammonia PW_R002516 L-Glutamic acid + L-Glutamate <> D-Glutamic acid PW_R002515 UDP-N-Acetylmuramoyl-L-alanine + Adenosine triphosphate + D-Glutamic acid > Adenosine diphosphate + Phosphate + UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + ADP + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate PW_R002518 UDP-N-Acetylmuramyl-L-Ala + Adenosine triphosphate + D-Glutamic acid > UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate + ADP + Phosphate PW_R006033 D-Glutamine + Water <> D-Glutamic acid + Ammonia Adenosine triphosphate + D-Glutamic acid + UDP-N-Acetylmuramoyl-L-alanine <> ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate D-Glutamic acid <> L-Glutamate Adenosine triphosphate + D-Glutamic acid + UDP-N-Acetylmuramoyl-L-alanine <> ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate D-Glutamic acid <> L-Glutamate