2.0 2012-07-30 14:55:06 -0600 2015-06-03 17:21:00 -0600 ECMDB21250 M2MDB001658 N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tripeptide N-acetyl-D-glucosamine(anhydrous)N-acetylmuramyl-tripeptide 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. C34H54N6O19 850.8214 850.344373576 2-amino-6-{[4-carboxy-2-({2-[(2-{[3-({4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl}oxy)-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)-3,4-dihydro-2H-pyran-4-yl]oxy}-1-hydroxypropylidene)amino]-1-hydroxypropylidene}amino)-1-hydroxybutylidene]amino}heptanedioic acid 2-amino-6-{[4-carboxy-2-({2-[(2-{[3-({4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl}oxy)-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)-3,4-dihydro-2H-pyran-4-yl]oxy}-1-hydroxypropylidene)amino]-1-hydroxypropylidene}amino)-1-hydroxybutylidene]amino}heptanedioic acid CC(OC1C(OC2OC(CO)C(O)C(O)C2N=C(C)O)C(CO)OC=C1N=C(C)O)C(O)=NC(C)C(O)=NC(CCC(O)=O)C(O)=NC(CCCC(N)C(O)=O)C(O)=O InChI=1S/C34H54N6O19/c1-13(29(49)39-18(8-9-23(45)46)31(51)40-19(33(54)55)7-5-6-17(35)32(52)53)36-30(50)14(2)57-27-20(37-15(3)43)12-56-22(11-42)28(27)59-34-24(38-16(4)44)26(48)25(47)21(10-41)58-34/h12-14,17-19,21-22,24-28,34,41-42,47-48H,5-11,35H2,1-4H3,(H,36,50)(H,37,43)(H,38,44)(H,39,49)(H,40,51)(H,45,46)(H,52,53)(H,54,55) ZWZMFRJKRXDGBE-UHFFFAOYSA-N Cytosol Periplasm logp -1.59 ALOGPS logs -3.64 ALOGPS solubility 1.97e-01 g/l ALOGPS logp -2.8 ChemAxon pka_strongest_acidic 3.23 ChemAxon iupac 2-amino-6-{[4-carboxy-2-({2-[(2-{[3-({4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl}oxy)-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)-3,4-dihydro-2H-pyran-4-yl]oxy}-1-hydroxypropylidene)amino]-1-hydroxypropylidene}amino)-1-hydroxybutylidene]amino}heptanedioic acid ChemAxon average_mass 850.8214 ChemAxon mono_mass 850.344373576 ChemAxon smiles CC(OC1C(OC2OC(CO)C(O)C(O)C2N=C(C)O)C(CO)OC=C1N=C(C)O)C(O)=NC(C)C(O)=NC(CCC(O)=O)C(O)=NC(CCCC(N)C(O)=O)C(O)=O ChemAxon formula C34H54N6O19 ChemAxon inchi InChI=1S/C34H54N6O19/c1-13(29(49)39-18(8-9-23(45)46)31(51)40-19(33(54)55)7-5-6-17(35)32(52)53)36-30(50)14(2)57-27-20(37-15(3)43)12-56-22(11-42)28(27)59-34-24(38-16(4)44)26(48)25(47)21(10-41)58-34/h12-14,17-19,21-22,24-28,34,41-42,47-48H,5-11,35H2,1-4H3,(H,36,50)(H,37,43)(H,38,44)(H,39,49)(H,40,51)(H,45,46)(H,52,53)(H,54,55) ChemAxon inchikey ZWZMFRJKRXDGBE-UHFFFAOYSA-N ChemAxon polar_surface_area 418.71 ChemAxon refractivity 194.05 ChemAxon polarizability 82.91 ChemAxon rotatable_bond_count 23 ChemAxon acceptor_count 25 ChemAxon donor_count 13 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 37160 Specdb::MsMs 37161 Specdb::MsMs 37162 Specdb::MsMs 39608 Specdb::MsMs 39609 Specdb::MsMs 39610 45479614 CPD0-2155 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 two linked disacharide tripeptide murein units (uncrosslinked, middle of chain) >2 N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tripeptide N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tripeptide + Water > L-alanine-D-glutamate-meso-2,6-diaminoheptanedioate + N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramic acid N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tripeptide + Water > N-Acetyl-D-glucosamine + 1,6-Anhydrous-N-Acetylmuramyl-tripeptide N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tetrapeptide + Water > D-Alanine + N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tripeptide