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Record Information
Version	2.0
Creation Date	2012-05-31 14:32:58 -0600
Update Date	2015-06-03 17:19:31 -0600
Secondary Accession Numbers	ECMDB20203
Identification
Name:	UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate
Description	UDP-N-acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate is a peptide. It 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-D-glucosamine, yielding the complete monomeric unit a lipid II, also known as lipid II. 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.
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa6f0f2e8> Close
Synonyms:	UDP-N-acetylmuramoyl-L-alanyl-γ-D-glutamyl-meso-diaminopimelate UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate UDP-MurNAc-L-Ala-D-Glu-meso-A2pm UDP-MurNAc-L-Ala-D-Glu-meso-A2pm UDP-n-Acetylmuramoyl-L-alanyl-γ-D-glutamyl-meso-diaminopimelate UDP-n-Acetylmuramoyl-L-alanyl-γ-D-glutamyl-meso-diaminopimelic acid UDP-N-acetylmuramoyl-L-alanyl-D-γ-glutamyl-meso-2,6-diaminopimelate UDP-N-Acetylmuramoyl-L-alanyl-D-γ-glutamyl-meso-2,6-diaminopimelate UDP-N-Acetylmuramoyl-L-alanyl-D-γ-glutamyl-meso-2,6-diaminopimelic acid UDP-N-Acetylmuramoyl-L-alanyl-D-g-glutamyl-meso-2,6-diaminopimelate UDP-N-Acetylmuramoyl-L-alanyl-D-g-glutamyl-meso-2,6-diaminopimelic acid UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelic acid UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioic acid UDP-N-Acetylmuramoyl-L-alanyl-D-γ-glutamyl-meso-2,6-diaminopimelate UDP-N-Acetylmuramoyl-L-alanyl-D-γ-glutamyl-meso-2,6-diaminopimelic acid UDP-N-Acetylmuramoyl-L-alanyl-g-D-glutamyl-meso-diaminopimelate UDP-N-Acetylmuramoyl-L-alanyl-g-D-glutamyl-meso-diaminopimelic acid UDP-N-Acetylmuramoyl-L-alanyl-gamma-D-glutamyl-meso-diaminopimelate UDP-N-Acetylmuramoyl-L-alanyl-gamma-D-glutamyl-meso-diaminopimelic acid UDP-N-Acetylmuramoyl-L-alanyl-γ-D-glutamyl-meso-diaminopimelate UDP-N-Acetylmuramoyl-L-alanyl-γ-D-glutamyl-meso-diaminopimelic acid
Chemical Formula:	C35H55N7O26P2
Weight:	Average: 1051.79 Monoisotopic: 1051.267197991
InChI Key:	QUHLBZKCGUXHGP-IBSIGGROSA-N
InChI:	InChI=1S/C35H55N7O26P2/c1-13(28(50)40-18(33(56)57)7-8-21(45)39-17(32(54)55)6-4-5-16(36)31(52)53)37-29(51)14(2)64-27-23(38-15(3)44)34(66-19(11-43)25(27)48)67-70(61,62)68-69(59,60)63-12-20-24(47)26(49)30(65-20)42-10-9-22(46)41-35(42)58/h9-10,13-14,16-20,23-27,30,34,43,47-49H,4-8,11-12,36H2,1-3H3,(H,37,51)(H,38,44)(H,39,45)(H,40,50)(H,52,53)(H,54,55)(H,56,57)(H,59,60)(H,61,62)(H,41,46,58)/t13-,14?,16?,17?,18+,19+,20+,23+,24+,25+,26+,27+,30+,34+/m0/s1
CAS number:	Not Available
IUPAC Name:	2-amino-6-{[(4R)-4-carboxy-4-{[(2S)-2-[(2-{[(2R,3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-1-hydroxypropylidene)amino]-1-hydroxypropylidene]amino}-1-hydroxybutylidene]amino}heptanedioic acid
Traditional IUPAC Name:	2-amino-6-{[(4R)-4-carboxy-4-{[(2S)-2-[(2-{[(2R,3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-4-yl]oxy}-1-hydroxypropylidene)amino]-1-hydroxypropylidene]amino}-1-hydroxybutylidene]amino}heptanedioic acid
SMILES:	[H]C(N)(CCCC([H])(N=C(O)CC[C@@]([H])(N=C(O)[C@]([H])(C)N=C(O)C([H])(C)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)O[C@]([H])(OP(O)(=O)OP(O)(=O)OC[C@@]2([H])O[C@@]([H])(N3C=CC(O)=NC3=O)[C@]([H])(O)[C@]2([H])O)[C@]1([H])N=C(C)O)C(O)=O)C(O)=O)C(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.
Kingdom	Organic compounds
Super Class	Nucleosides, nucleotides, and analogues
Class	Pyrimidine nucleotides
Sub Class	Pyrimidine nucleotide sugars
Direct Parent	Pyrimidine nucleotide sugars
Alternative Parents	Pyrimidine ribonucleoside diphosphates Peptides Saccharolipids Pentose phosphates N-acyl-alpha-hexosamines N-acyl-alpha amino acids Glycosylamines Organic pyrophosphates Monosaccharide phosphates Alpha amino acids Tricarboxylic acids and derivatives Pyrimidones Monoalkyl phosphates Hydroxypyrimidines Hydroxy fatty acids Amino fatty acids Oxanes Hydropyrimidines Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Amino acids Propargyl-type 1,3-dipolar organic compounds Oxacyclic compounds Dialkyl ethers Carboxylic acids Carboximidic acids Azacyclic compounds Primary alcohols Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
Substituents	Pyrimidine nucleotide sugar Pyrimidine ribonucleoside diphosphate Alpha peptide Saccharolipid Pentose-5-phosphate Pentose phosphate N-acyl-alpha-hexosamine N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid N-glycosyl compound Glycosyl compound Organic pyrophosphate Monosaccharide phosphate Alpha-amino acid or derivatives Alpha-amino acid Tricarboxylic acid or derivatives Hydroxypyrimidine Monoalkyl phosphate Pyrimidone Hydroxy fatty acid Amino fatty acid Fatty acyl Alkyl phosphate Pyrimidine Phosphoric acid ester Oxane Organic phosphoric acid derivative Monosaccharide Hydropyrimidine Heteroaromatic compound Tetrahydrofuran Amino acid Secondary alcohol Amino acid or derivatives Oxacycle Azacycle Organoheterocyclic compound Organic 1,3-dipolar compound Propargyl-type 1,3-dipolar organic compound Ether Dialkyl ether Carboxylic acid Carboxylic acid derivative Carboximidic acid derivative Carboximidic acid Organic nitrogen compound Organic oxygen compound Organopnictogen compound Organic oxide Hydrocarbon derivative Primary amine Primary alcohol Organooxygen compound Organonitrogen compound Primary aliphatic amine Carbonyl group Amine Alcohol Aromatic heteromonocyclic compound
Molecular Framework	Aromatic heteromonocyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-3
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 1.08 g/L ALOGPS logP -0.71 ALOGPS logP -3.4 ChemAxon logS -3 ALOGPS pKa (Strongest Acidic) 1.72 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 29 ChemAxon Hydrogen Donor Count 15 ChemAxon Polar Surface Area 532.08 Ų ChemAxon Rotatable Bond Count 27 ChemAxon Refractivity 221.12 m³·mol⁻¹ ChemAxon Polarizability 94.84 ų ChemAxon Number of Rings 3 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + Meso-2,6-Diaminoheptanedioate + Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate > Adenosine diphosphate + Phosphate + Hydrogen ion + UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate + ADP UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate + D-Alanyl-D-alanine + Adenosine triphosphate > Adenosine diphosphate + Phosphate + Hydrogen ion + UDP-N-acetyl-α-D-muramoyl-L-alanyl-γ-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine + ADP UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate + D-Alanyl-D-alanine + Adenosine triphosphate > N-Acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine-diphosphoundecaprenyl-N-acetylglucosamine + ADP + Phosphate + Hydrogen ion
SMPDB Pathways:	Lysine biosynthesis PW000771 peptidoglycan biosynthesis I PW000906 peptidoglycan biosynthesis I 2 PW002062
KEGG Pathways:	Lysine biosynthesis ec00300 Peptidoglycan biosynthesis ec00550
EcoCyc Pathways:	UDP-N-acetylmuramoyl-pentapeptide biosynthesis III (meso-DAP-containing) PWY-6387
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-03di-3902000000-768b4205c31ec38d912d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-03di-2902000100-52dd4e66fad9a96a043d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-03di-2902000000-64773990e7770fc9b147 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0il3-9401202002-b84c4eb76b090b642d65 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-01qc-9504110220-9967e6e46a6cd500f0f7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-06tf-4913110000-75ad36f025dc10e827ee View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 28639 HMDB ID Not Available Pubchem Compound ID 23724481 Kegg ID C04877 ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID UDP-AAGM-DIAMINOHEPTANEDIOATE EcoCyc ID UDP-AAGM-DIAMINOHEPTANEDIOATE

Enzymes