2.0 2012-10-10 12:18:51 -0600 2015-06-03 17:26:01 -0600 ECMDB23146 M2MDB003536 GlcNAc-MurNAc-L-alanyl-gamma-D-glutamyl-meso-diaminopimelyl-D-alanine GlcNAc-MurNAc-L-alanyl-gamma-D-glutamyl-meso-diaminopimelyl-D-alanine is an intermediate in peptidoglycan recylcing and biosynthesis. It is a substrate for the enzyme Murein tetrapeptide carboxypeptidase (lcdA) which releases the terminal D-alanine residue from the cytoplasmic tetrapeptide recycling product L-Ala-gamma-D-Glu-meso-Dap-D-Ala. The tripeptides produced by the lcdA reaction can then be reused as peptidoglycan building blocks. GlcNAc-murnac-L-alanyl-g-D-glutamyl-meso-diaminopimelyl-D-alanine GlcNAc-murnac-L-alanyl-γ-D-glutamyl-meso-diaminopimelyl-D-alanine C34H57N7O19 867.8519 867.370922677 (2S,6R)-2-amino-6-{[(2R)-4-carboxy-2-{[(2S)-2-{[(2R,3R,4R,5S,6R)-5-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]amino}-1-hydroxypropylidene]amino}-1-hydroxybutylidene]amino}-6-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}hexanoic acid (2S,6R)-2-amino-6-{[(2R)-4-carboxy-2-{[(2S)-2-{[(2R,3R,4R,5S,6R)-5-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]amino}-1-hydroxypropylidene]amino}-1-hydroxybutylidene]amino}-6-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}hexanoic acid [H][C@](N)(CCC[C@@]([H])(N=C(O)[C@@]([H])(CCC(O)=O)N=C(O)[C@]([H])(C)N[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O[C@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])N=C(C)O)[C@]([H])(O)[C@@]1([H])N=C(C)O)C(O)=N[C@]([H])(C)C(O)=O)C(O)=O InChI=1S/C34H57N7O19/c1-12(28(51)40-18(8-9-21(46)47)30(53)41-17(7-5-6-16(35)33(56)57)29(52)36-13(2)32(54)55)37-31-22(38-14(3)44)26(50)27(20(11-43)58-31)60-34-23(39-15(4)45)25(49)24(48)19(10-42)59-34/h12-13,16-20,22-27,31,34,37,42-43,48-50H,5-11,35H2,1-4H3,(H,36,52)(H,38,44)(H,39,45)(H,40,51)(H,41,53)(H,46,47)(H,54,55)(H,56,57)/t12-,13+,16-,17+,18+,19+,20+,22+,23+,24+,25+,26+,27+,31+,34-/m0/s1 MKQQKXDNMLOSJC-YFCMHDTQSA-N logp -1.97 ALOGPS logs -3.76 ALOGPS solubility 1.51e-01 g/l ALOGPS logp -3.2 ChemAxon pka_strongest_acidic 3.31 ChemAxon iupac (2S,6R)-2-amino-6-{[(2R)-4-carboxy-2-{[(2S)-2-{[(2R,3R,4R,5S,6R)-5-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]amino}-1-hydroxypropylidene]amino}-1-hydroxybutylidene]amino}-6-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}hexanoic acid ChemAxon average_mass 867.8519 ChemAxon mono_mass 867.370922677 ChemAxon smiles [H][C@](N)(CCC[C@@]([H])(N=C(O)[C@@]([H])(CCC(O)=O)N=C(O)[C@]([H])(C)N[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O[C@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])N=C(C)O)[C@]([H])(O)[C@@]1([H])N=C(C)O)C(O)=N[C@]([H])(C)C(O)=O)C(O)=O ChemAxon formula C34H57N7O19 ChemAxon inchi InChI=1S/C34H57N7O19/c1-12(28(51)40-18(8-9-21(46)47)30(53)41-17(7-5-6-16(35)33(56)57)29(52)36-13(2)32(54)55)37-31-22(38-14(3)44)26(50)27(20(11-43)58-31)60-34-23(39-15(4)45)25(49)24(48)19(10-42)59-34/h12-13,16-20,22-27,31,34,37,42-43,48-50H,5-11,35H2,1-4H3,(H,36,52)(H,38,44)(H,39,45)(H,40,51)(H,41,53)(H,46,47)(H,54,55)(H,56,57)/t12-,13+,16-,17+,18+,19+,20+,22+,23+,24+,25+,26+,27+,31+,34-/m0/s1 ChemAxon inchikey MKQQKXDNMLOSJC-YFCMHDTQSA-N ChemAxon polar_surface_area 441.74 ChemAxon refractivity 195.98 ChemAxon polarizability 84.28 ChemAxon rotatable_bond_count 23 ChemAxon acceptor_count 26 ChemAxon donor_count 15 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::EiMs 2832 Specdb::NmrOneD 332918 Specdb::NmrOneD 332919 Specdb::NmrOneD 332920 Specdb::NmrOneD 332921 Specdb::NmrOneD 332922 Specdb::NmrOneD 332923 Specdb::NmrOneD 332924 Specdb::NmrOneD 332925 Specdb::NmrOneD 332926 Specdb::NmrOneD 332927 Specdb::NmrOneD 332928 Specdb::NmrOneD 332929 Specdb::NmrOneD 332930 Specdb::NmrOneD 332931 Specdb::NmrOneD 332932 Specdb::NmrOneD 332933 Specdb::NmrOneD 332934 Specdb::NmrOneD 332935 Specdb::NmrOneD 332936 Specdb::NmrOneD 332937 Specdb::MsMs 36848 Specdb::MsMs 36849 Specdb::MsMs 36850 Specdb::MsMs 39296 Specdb::MsMs 39297 Specdb::MsMs 39298 Murein tetrapeptide carboxypeptidase P76008 LDCA_ECOLI ldcA http://ecmdb.ca/proteins/P76008.xml GlcNAc-MurNAc-L-alanyl-gamma-D-glutamyl-meso-diaminopimelyl-D-alanine + Water > GlcNAc-MurNAc-L-alanyl-gamma-D-glutamyl-meso-diaminopimelate + D-Alanine