2.0 2012-10-10 12:12:59 -0600 2015-06-03 17:25:45 -0600 ECMDB23024 M2MDB003414 GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol is an intermediate in peptidoglycan synthesis. It is a substrate for peptidoglycan glycosyltransferase (EC 2.4.1.129) which catalyzes the chemical reaction [GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)]n- diphosphoundecaprenol + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)- diphosphoundecaprenol <=> [GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)]n+1- diphosphoundecaprenol + undecaprenyl diphosphate. (2R)-2-(2S)-2-(2R)-2-(2R,3R,4R,5S,6R)-3-acetamido-5-(2S,3R,4R,5S,6R)-3-acetamido-4,5-Dihydroxy-6-(hydroxymethyl)oxan-2-yloxy-2-hydroxy-hydroxy-(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaenoxyphosphoryloxyphosphoryloxy-6-(hydroxymethyl)oxan-4-yloxypropanoylaminopropanoylamino-5-(2S)-6-amino-1-(2R)-1-(1R)-1-carboxyethylamino-1-oxopropan-2-ylamino-1-oxohexan-2-ylamino-5-oxopentanoate (2R)-2-(2S)-2-(2R)-2-(2R,3R,4R,5S,6R)-3-acetamido-5-(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yloxy-2-hydroxy-hydroxy-(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaenoxyphosphoryloxyphosphoryloxy-6-(hydroxymethyl)oxan-4-yloxypropanoylaminopropanoylamino-5-(2S)-6-amino-1-(2R)-1-(1R)-1-carboxyethylamino-1-oxopropan-2-ylamino-1-oxohexan-2-ylamino-5-oxopentanoic acid (2R,5R,8S,13R,16S,19R)-19-{(2R,3R,4R,5S,6R)-3-acetamido-5-{(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy}-2-({hydroxy(hydroxy{(2Z,6Z,10Z,14Z,18Z,22Z,26Z, 30Z,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecaen-1-yloxy}phosphoryl)oxyphosphoryl}oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yloxy}-8 -(4-aminobutyl)-13-carboxy-2,5,16-trimethyl-4,7,10,15,18-pentaoxo-3,6,9,14,17-pentaazaicosan-1-Oate (N (2R,5R,8S,13R,16S,19R)-19-{(2R,3R,4R,5S,6R)-3-Acetamido-5-{(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy}-2-({hydroxy(hydroxy{(2Z,6Z,10Z,14Z,18Z,22Z,26Z, 30Z,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecaen-1-yloxy}phosphoryl)oxyphosphoryl}oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yloxy}-8 -(4-aminobutyl)-13-carboxy-2,5,16-trimethyl-4,7,10,15,18-pentaoxo-3,6,9,14,17-pentaazaicosan-1-oic acid (n GlcNAc-(1->4)-mur2ac(oyl-L-ala-g-D-glu-L-lys-D-ala-D-ala)-diphosphoundecaprenol GlcNAc-(1->4)-mur2ac(oyl-L-ala-γ-D-glu-L-lys-D-ala-D-ala)-diphosphoundecaprenol Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-g-D-glutamyl-L-lysyl-D-alanyl-D-alanine Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-gamma-D-glutamyl-L-lysyl-D-alanyl-D-alanine Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-γ-D-glutamyl-L-lysyl-D-alanyl-D-alanine undecaprenyldiphospho-N-Acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-D-g-glutamyl-L-lysyl-D-alanyl-D-alanine Undecaprenyldiphospho-N-acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-D-gamma-glutamyl-L-lysyl-D-alanyl-D-alanine undecaprenyldiphospho-N-Acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-D-γ-glutamyl-L-lysyl-D-alanyl-D-alanine C94H156N8O26P2 1876.23 1875.060600228 (2R)-4-{[(1S)-5-amino-1-{[(1R)-1-{[(1R)-1-carboxyethyl]carbamoyl}ethyl]carbamoyl}pentyl]carbamoyl}-2-[(2S)-2-[(2R)-2-{[(2R,3R,4R,5S,6R)-3-acetamido-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-{[hydroxy({[hydroxy({[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxy})phosphoryl]oxy})phosphoryl]oxy}-6-(hydroxymethyl)oxan-4-yl]oxy}propanamido]propanamido]butanoic acid lipid II NCCCC[C@H](NC(=O)CC[C@@H](NC(=O)[C@H](C)NC(=O)[C@@H](C)O[C@H]1[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2NC(C)=O)[C@@H](CO)O[C@H](OP(O)(=O)OP(O)(=O)OC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)[C@@H]1NC(C)=O)C(O)=O)C(=O)N[C@H](C)C(=O)N[C@H](C)C(O)=O InChI=1S/C94H156N8O26P2/c1-59(2)31-21-32-60(3)33-22-34-61(4)35-23-36-62(5)37-24-38-63(6)39-25-40-64(7)41-26-42-65(8)43-27-44-66(9)45-28-46-67(10)47-29-48-68(11)49-30-50-69(12)54-56-122-129(118,119)128-130(120,121)127-94-82(100-75(18)106)86(85(79(58-104)125-94)126-93-81(99-74(17)105)84(109)83(108)78(57-103)124-93)123-73(16)89(112)96-71(14)88(111)102-77(92(116)117)52-53-80(107)101-76(51-19-20-55-95)90(113)97-70(13)87(110)98-72(15)91(114)115/h31,33,35,37,39,41,43,45,47,49,54,70-73,76-79,81-86,93-94,103-104,108-109H,19-30,32,34,36,38,40,42,44,46,48,50-53,55-58,95H2,1-18H3,(H,96,112)(H,97,113)(H,98,110)(H,99,105)(H,100,106)(H,101,107)(H,102,111)(H,114,115)(H,116,117)(H,118,119)(H,120,121)/b60-33+,61-35+,62-37-,63-39-,64-41-,65-43-,66-45-,67-47-,68-49-,69-54-/t70-,71+,72-,73-,76+,77-,78-,79-,81-,82-,83-,84-,85-,86-,93+,94-/m1/s1 ULXTYUPMJXVUHQ-OVTFQNCVSA-N Membrane logp 3.23 ALOGPS logs -5.78 ALOGPS solubility 3.10e-03 g/l ALOGPS logp 8.79 ChemAxon pka_strongest_acidic 1.71 ChemAxon pka_strongest_basic 10.19 ChemAxon iupac (2R)-4-{[(1S)-5-amino-1-{[(1R)-1-{[(1R)-1-carboxyethyl]carbamoyl}ethyl]carbamoyl}pentyl]carbamoyl}-2-[(2S)-2-[(2R)-2-{[(2R,3R,4R,5S,6R)-3-acetamido-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-{[hydroxy({[hydroxy({[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl]oxy})phosphoryl]oxy})phosphoryl]oxy}-6-(hydroxymethyl)oxan-4-yl]oxy}propanamido]propanamido]butanoic acid ChemAxon average_mass 1876.23 ChemAxon mono_mass 1875.060600228 ChemAxon smiles NCCCC[C@H](NC(=O)CC[C@@H](NC(=O)[C@H](C)NC(=O)[C@@H](C)O[C@H]1[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2NC(C)=O)[C@@H](CO)O[C@H](OP(O)(=O)OP(O)(=O)OC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)[C@@H]1NC(C)=O)C(O)=O)C(=O)N[C@H](C)C(=O)N[C@H](C)C(O)=O ChemAxon formula C94H156N8O26P2 ChemAxon inchi InChI=1S/C94H156N8O26P2/c1-59(2)31-21-32-60(3)33-22-34-61(4)35-23-36-62(5)37-24-38-63(6)39-25-40-64(7)41-26-42-65(8)43-27-44-66(9)45-28-46-67(10)47-29-48-68(11)49-30-50-69(12)54-56-122-129(118,119)128-130(120,121)127-94-82(100-75(18)106)86(85(79(58-104)125-94)126-93-81(99-74(17)105)84(109)83(108)78(57-103)124-93)123-73(16)89(112)96-71(14)88(111)102-77(92(116)117)52-53-80(107)101-76(51-19-20-55-95)90(113)97-70(13)87(110)98-72(15)91(114)115/h31,33,35,37,39,41,43,45,47,49,54,70-73,76-79,81-86,93-94,103-104,108-109H,19-30,32,34,36,38,40,42,44,46,48,50-53,55-58,95H2,1-18H3,(H,96,112)(H,97,113)(H,98,110)(H,99,105)(H,100,106)(H,101,107)(H,102,111)(H,114,115)(H,116,117)(H,118,119)(H,120,121)/b60-33+,61-35+,62-37-,63-39-,64-41-,65-43-,66-45-,67-47-,68-49-,69-54-/t70-,71+,72-,73-,76+,77-,78-,79-,81-,82-,83-,84-,85-,86-,93+,94-/m1/s1 ChemAxon inchikey ULXTYUPMJXVUHQ-OVTFQNCVSA-N ChemAxon polar_surface_area 524.45 ChemAxon refractivity 503.83 ChemAxon polarizability 202.75 ChemAxon rotatable_bond_count 63 ChemAxon acceptor_count 24 ChemAxon donor_count 16 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Specdb::EiMs 5205 Specdb::MsMs 3619161 Specdb::MsMs 3619162 Specdb::MsMs 3619163 Specdb::MsMs 3619164 Specdb::MsMs 3619165 Specdb::MsMs 3619166 46173749 C05893 27692 Penicillin-binding protein 1B P02919 PBPB_ECOLI mrcB http://ecmdb.ca/proteins/P02919.xml Peptidoglycan synthase ftsI P0AD68 FTSI_ECOLI ftsI http://ecmdb.ca/proteins/P0AD68.xml UDP-N-acetylglucosamine--N-acetylmuramyl-(pentapeptide) pyrophosphoryl-undecaprenol N-acetylglucosamine transferase P17443 MURG_ECOLI murG http://ecmdb.ca/proteins/P17443.xml (GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala))(n)-diphosphoundecaprenol + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol > (GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala))(n+1)-diphosphoundecaprenol + Undecaprenyl diphosphate Uridine diphosphate-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol > Uridine 5'-diphosphate + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol