2.0 2012-07-30 14:55:06 -0600 2015-06-03 17:21:00 -0600 ECMDB21249 M2MDB001657 N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tetrapeptide N-acetyl-D-glucosamine(anhydrous)N-acetylmuramyl-tetrapeptide is an intermediate in peptidoglycan synthesis and turnover. Peptidoglycan can be described as a fisherman's net that encloses bacteria. The mesh of the net is made of two segments of parallel, somewhat inextensible glycan threads, held together by two small elastic peptide crosslinks allowing the net to expand or shrink. The glycan moiety of the peptidoglycan is very uniform among all bacteria, and is made up of alternating β-1,4-linked N-acetylglucosamine and N-acetyl muramate residues, with an average chain lengthof 10 to 65 disaccharide units (depending on the organism). The peptidoglycan synthesis pathway starts in 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-α-D-glucosamine, yielding the complete monomeric unit a lipid II, also known as lipid II. This final lipid intermediate is transferred by an as yet unknown mechanism 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. Peptide crosslinks form between different parts of the peptides depending on the organism. For example, in Mycobacteria and in E. coli most links form between the carboxyl group of the penultimate D-alanine (residue 4) of one peptide to the amino group at the D-center of meso-diaminopimelate (residue 3) of an adjacent peptide of a second glycan chain (as in E. coli). The crosslinking reaction is catalyzed by transpeptidases and involves the cleavage of the D-alanyl-D-alanine bond of the donor peptide, providing the energy to drive the reaction. As a result, the peptides in the peptidoglycan polymers are one or two amino acids shorter than the peptides in the monomers. C37H59N7O20 921.8993 921.381487363 2-amino-6-{[4-carboxy-2-({2-[(2-{[(3R,4R)-2-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-4-[(1-hydroxyethylidene)amino]-6,8-dioxabicyclo[3.2.1]octan-3-yl]oxy}-1-hydroxypropylidene)amino]-1-hydroxypropylidene}amino)-1-hydroxybutylidene]amino}-6-[(1-carboxyethyl)-C-hydroxycarbonimidoyl]hexanoic acid 2-amino-6-{[4-carboxy-2-({2-[(2-{[(3R,4R)-2-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-4-[(1-hydroxyethylidene)amino]-6,8-dioxabicyclo[3.2.1]octan-3-yl]oxy}-1-hydroxypropylidene)amino]-1-hydroxypropylidene}amino)-1-hydroxybutylidene]amino}-6-[(1-carboxyethyl)-C-hydroxycarbonimidoyl]hexanoic acid [H]C(N)(CCCC([H])(N=C(O)C([H])(CCC(O)=O)N=C(O)C([H])(C)N=C(O)C([H])(C)O[C@@]1([H])C([H])(O[C@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])N=C(C)O)C2([H])COC([H])(O2)[C@]1([H])N=C(C)O)C(O)=NC([H])(C)C(O)=O)C(O)=O InChI=1S/C37H59N7O20/c1-13(30(52)43-20(9-10-23(48)49)33(55)44-19(8-6-7-18(38)35(58)59)32(54)40-14(2)34(56)57)39-31(53)15(3)61-29-25(42-17(5)47)36-60-12-22(63-36)28(29)64-37-24(41-16(4)46)27(51)26(50)21(11-45)62-37/h13-15,18-22,24-29,36-37,45,50-51H,6-12,38H2,1-5H3,(H,39,53)(H,40,54)(H,41,46)(H,42,47)(H,43,52)(H,44,55)(H,48,49)(H,56,57)(H,58,59)/t13?,14?,15?,18?,19?,20?,21-,22?,24-,25-,26-,27-,28?,29-,36?,37+/m1/s1 ZTOWCORYLXDAAW-JOUWMGDHSA-N Cytosol Periplasm logp -1.32 ALOGPS logs -3.53 ALOGPS solubility 2.73e-01 g/l ALOGPS logp -1.5 ChemAxon pka_strongest_acidic 3.27 ChemAxon iupac 2-amino-6-{[4-carboxy-2-({2-[(2-{[(3R,4R)-2-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-4-[(1-hydroxyethylidene)amino]-6,8-dioxabicyclo[3.2.1]octan-3-yl]oxy}-1-hydroxypropylidene)amino]-1-hydroxypropylidene}amino)-1-hydroxybutylidene]amino}-6-[(1-carboxyethyl)-C-hydroxycarbonimidoyl]hexanoic acid ChemAxon average_mass 921.8993 ChemAxon mono_mass 921.381487363 ChemAxon smiles [H]C(N)(CCCC([H])(N=C(O)C([H])(CCC(O)=O)N=C(O)C([H])(C)N=C(O)C([H])(C)O[C@@]1([H])C([H])(O[C@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])N=C(C)O)C2([H])COC([H])(O2)[C@]1([H])N=C(C)O)C(O)=NC([H])(C)C(O)=O)C(O)=O ChemAxon formula C37H59N7O20 ChemAxon inchi InChI=1S/C37H59N7O20/c1-13(30(52)43-20(9-10-23(48)49)33(55)44-19(8-6-7-18(38)35(58)59)32(54)40-14(2)34(56)57)39-31(53)15(3)61-29-25(42-17(5)47)36-60-12-22(63-36)28(29)64-37-24(41-16(4)46)27(51)26(50)21(11-45)62-37/h13-15,18-22,24-29,36-37,45,50-51H,6-12,38H2,1-5H3,(H,39,53)(H,40,54)(H,41,46)(H,42,47)(H,43,52)(H,44,55)(H,48,49)(H,56,57)(H,58,59)/t13?,14?,15?,18?,19?,20?,21-,22?,24-,25-,26-,27-,28?,29-,36?,37+/m1/s1 ChemAxon inchikey ZTOWCORYLXDAAW-JOUWMGDHSA-N ChemAxon polar_surface_area 440.3 ChemAxon refractivity 208.61 ChemAxon polarizability 88.32 ChemAxon rotatable_bond_count 24 ChemAxon acceptor_count 27 ChemAxon donor_count 13 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Specdb::EiMs 5027 Specdb::NmrOneD 301145 Specdb::NmrOneD 301146 Specdb::NmrOneD 301147 Specdb::NmrOneD 301148 Specdb::NmrOneD 301149 Specdb::NmrOneD 301150 Specdb::NmrOneD 301151 Specdb::NmrOneD 301152 Specdb::NmrOneD 301153 Specdb::NmrOneD 301154 Specdb::NmrOneD 301155 Specdb::NmrOneD 301156 Specdb::NmrOneD 301157 Specdb::NmrOneD 301158 Specdb::NmrOneD 301159 Specdb::NmrOneD 301160 Specdb::NmrOneD 301161 Specdb::NmrOneD 301162 Specdb::NmrOneD 301163 Specdb::NmrOneD 301164 Specdb::MsMs 36698 Specdb::MsMs 36699 Specdb::MsMs 36700 Specdb::MsMs 39146 Specdb::MsMs 39147 Specdb::MsMs 39148 45479403 CPD0-2292 N-acetylmuramoyl-L-alanine amidase AmiB P26365 AMIB_ECOLI amiB http://ecmdb.ca/proteins/P26365.xml Probable N-acetylmuramoyl-L-alanine amidase AmiA P36548 AMIA_ECOLI amiA http://ecmdb.ca/proteins/P36548.xml N-acetylmuramoyl-L-alanine amidase AmiC P63883 AMIC_ECOLI amiC http://ecmdb.ca/proteins/P63883.xml Beta-hexosaminidase P75949 NAGZ_ECOLI nagZ http://ecmdb.ca/proteins/P75949.xml Murein tetrapeptide carboxypeptidase P76008 LDCA_ECOLI ldcA http://ecmdb.ca/proteins/P76008.xml Soluble lytic murein transglycosylase P0AGC3 SLT_ECOLI slt http://ecmdb.ca/proteins/P0AGC3.xml Endo-type membrane-bound lytic murein transglycosylase A P0C960 EMTA_ECOLI emtA http://ecmdb.ca/proteins/P0C960.xml Membrane-bound lytic murein transglycosylase C P0C066 MLTC_ECOLI mltC http://ecmdb.ca/proteins/P0C066.xml Membrane-bound lytic murein transglycosylase F P0AGC5 MLTF_ECOLI mltF http://ecmdb.ca/proteins/P0AGC5.xml Membrane-bound lytic murein transglycosylase B P41052 MLTB_ECOLI mltB http://ecmdb.ca/proteins/P41052.xml 1,6-anhydro-N-acetylmuramyl-L-alanine amidase AmpD P13016 AMPD_ECOLI ampD http://ecmdb.ca/proteins/P13016.xml Membrane-bound lytic murein transglycosylase A P0A935 MLTA_ECOLI mltA http://ecmdb.ca/proteins/P0A935.xml Protein AmpG P0AE16 AMPG_ECOLI ampG http://ecmdb.ca/proteins/P0AE16.xml two linked disacharide tetrapeptide and tripeptide murein units (uncrosslinked, middle of chain) > N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tripeptide + N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tetrapeptide N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tetrapeptide + Water > L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine + N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramic acid two linked disacharide tetrapeptide murein units (uncrosslinked, middle of chain) >2 N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tetrapeptide three disacharide linked murein units (tetrapeptide crosslinked tetrapeptide (A2pm->D-ala), one uncrosslinked tetrapaptide) (middle of chain) > N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tetrapeptide + two disacharide linked murein units, tetrapeptide corsslinked tetrapeptide (A2pm->D-ala) (middle of chain) N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tetrapeptide + Water > N-Acetyl-D-glucosamine + 1,6-Anhydrous-N-Acetylmuramyl-tetrapeptide N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tetrapeptide + Water > D-Alanine + N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tripeptide