Record Information
Version2.0
Creation Date2012-05-31 14:07:15 -0600
Update Date2015-06-03 15:54:49 -0600
Secondary Accession Numbers
  • ECMDB04170
Identification
Name:UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate
DescriptionUDP-n-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate is a member of the chemical class known as Peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. 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-alpha-D-glucosamine, yielding the complete monomeric unit a lipid , also known as lipid . 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
Thumb
Synonyms:
  • UDP-N-acetylmuramoyl-L-alanyl-γ-D-glutamyl-meso-diaminopimelate
  • UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate
  • UDP-Aagm-diaminoheptanedioate
  • UDP-Aagm-diaminoheptanedioic acid
  • UDP-MurNAc-L-Ala-D-Glu-meso-A2pm
  • UDP-MurNAc-L-Ala-D-Glu-meso-A2pm
  • UDP-MurNAc-L-Ala-D-Glu-mesoA2pm
  • 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-diaminopimelate
  • UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelic acid
  • 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:C35H51N7O26P2
Weight:Average: 1047.7583
Monoisotopic: 1047.235897863
InChI Key:QUHLBZKCGUXHGP-BHBBPGSKSA-J
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)/p-4/t13-,14+,16+,17-,18+,19+,20+,23+,24+,25+,26+,27+,30+,34+/m0/s1
CAS number:Not Available
IUPAC Name:(4R)-N-[(1S,5R)-5-amino-1,5-dicarboxypentyl]-4-carboxy-4-{[(2S)-2-{[(2R)-2-{[(2R,3R,4R,5S,6R)-2-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-oxido-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-5-hydroxy-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]oxan-4-yl]oxy}-1-hydroxypropylidene]amino}-1-oxidopropylidene]amino}butanecarboximidate
Traditional IUPAC Name:(4R)-N-[(1S,5R)-5-amino-1,5-dicarboxypentyl]-4-carboxy-4-{[(2S)-2-{[(2R)-2-{[(2R,3R,4R,5S,6R)-2-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-oxido-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-5-hydroxy-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]oxan-4-yl]oxy}-1-hydroxypropylidene]amino}-1-oxidopropylidene]amino}butanecarboximidate
SMILES:[H][C@@](N)(CCC[C@]([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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine nucleotide sugars
Direct ParentPyrimidine nucleotide sugars
Alternative Parents
Substituents
  • Pyrimidine nucleotide sugar
  • Pyrimidine ribonucleoside diphosphate
  • Alpha-dipeptide
  • Gamma-glutamyl alpha-amino acid
  • Alpha peptide
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glutamine or derivatives
  • N-acyl-alpha-hexosamine
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid amide
  • Glycosyl compound
  • N-glycosyl compound
  • Alanine or derivatives
  • D-alpha-amino acid
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Pyrimidone
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Fatty acyl
  • Pyrimidine
  • N-acyl-amine
  • Hydropyrimidine
  • Fatty amide
  • Oxane
  • Phosphoric acid ester
  • Monosaccharide
  • Acetamide
  • Vinylogous amide
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Lactam
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Urea
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Carboxylic acid salt
  • Azacycle
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Organooxygen compound
  • Primary amine
  • Amine
  • Organic salt
  • Hydrocarbon derivative
  • Primary alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Alcohol
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic anion
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
  • UDP-N-acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminoheptanedioate(4-) (CHEBI:83905 )
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility4 g/LALOGPS
logP-0.82ALOGPS
logP-3.4ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)1.72ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count29ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area543.4 ŲChemAxon
Rotatable Bond Count27ChemAxon
Refractivity263.32 m³·mol⁻¹ChemAxon
Polarizability92.98 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Diaminopimelic acid + Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate > ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate
D-Alanyl-D-alanine + Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate > ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine
Water + UDP-N-acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diaminopimelate-D-alanine > D-Alanine + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate
L-alanine-D-glutamate-meso-2,6-diaminoheptanedioate + Adenosine triphosphate + UDP-N-Acetylmuraminate > ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate
Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate + Meso-2,6-Diaminoheptanedioate <> ADP + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate
Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate + D-Alanyl-D-alanine <> ADP + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine
UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate-D-alanine + Water > L-Alanine + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate
UDP-N-Acetylmuraminate + L-Ala-D-Glu-meso-A2pm + Adenosine triphosphate > Hydrogen ion + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate + ADP + Phosphate
<i>meso</i>-diaminopimelate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate + Adenosine triphosphate > Hydrogen ion + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate + Phosphate + ADP
D-Alanyl-D-alanine + Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate > ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine
Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate + Meso-2,6-Diaminoheptanedioate <> ADP + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate
D-Alanyl-D-alanine + Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate > ADP + Hydrogen ion + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-6-carboxy-L-lysyl-D-alanyl-D-alanine
Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamate + Meso-2,6-Diaminoheptanedioate <> ADP + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioate
SMPDB Pathways:
Lysine biosynthesisPW000771 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
  • UDP-N-acetylmuramoyl-pentapeptide biosynthesis III (meso-DAP-containing) PWY-6387
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052b-9000000000-93b5c36a79fcf09f13d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0btc-9000000000-51746bb1471a6d81a5a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000110-8a01cd074258d2ff07f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4m-9000000000-f58d2052cef4e479229aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aba-9000000000-4b079078403481aad574View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06uu-9300000000-8c1109c8031b33c29738View in MoNA
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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID28639
HMDB IDNot Available
Pubchem Compound ID25243985
Kegg IDC04877
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDUDP-AAGM-DIAMINOHEPTANEDIOATE
EcoCyc IDUDP-AAGM-DIAMINOHEPTANEDIOATE

Enzymes

General function:
Involved in ATP binding
Specific function:
Involved in cell wall formation. Catalyzes the final step in the synthesis of UDP-N-acetylmuramoyl-pentapeptide, the precursor of murein
Gene Name:
murF
Uniprot ID:
P11880
Molecular weight:
47447
Reactions
ATP + UDP-N-acetylmuramoyl-L-alanyl-gamma-D-glutamyl-L-lysine + D-alanyl-D-alanine = ADP + phosphate + UDP-N-acetylmuramoyl-L-alanyl-gamma-D-glutamyl-L-lysyl-D-alanyl-D-alanine.
General function:
Involved in ATP binding
Specific function:
Catalyzes the addition of meso-diaminopimelic acid to the nucleotide precursor UDP-N-acetylmuramoyl-L-alanyl-D-glutamate (UMAG) in the biosynthesis of bacterial cell-wall peptidoglycan. Is also able to use many meso-diaminopimelate analogs as substrates, although much less efficiently, but not L-lysine
Gene Name:
murE
Uniprot ID:
P22188
Molecular weight:
53343
Reactions
ATP + UDP-N-acetylmuramoyl-L-alanyl-D-glutamate + meso-2,6-diaminoheptanedioate = ADP + phosphate + UDP-N-acetylmuramoyl-L-alanyl-D-gamma-glutamyl-meso-2,6-diamino-heptanedioate.
General function:
Defense mechanisms
Specific function:
Releases the terminal D-alanine residue from the cytoplasmic tetrapeptide recycling product L-Ala-gamma-D-Glu-meso- Dap-D-Ala. To a lesser extent, can also cleave D-Ala from murein derivatives containing the tetrapeptide, i.e. MurNAc-tetrapeptide, UDP-MurNAc-tetrapeptide, GlcNAc-MurNAc-tetrapeptide, and GlcNAc- anhMurNAc-tetrapeptide. Does not act on murein sacculi or cross- linked muropeptides. The tripeptides produced by the lcdA reaction can then be reused as peptidoglycan building blocks; lcdA is thereby involved in murein recycling. Is also essential for viability during stationary phase
Gene Name:
ldcA
Uniprot ID:
P76008
Molecular weight:
33567
Reactions
GlcNAc-MurNAc-L-alanyl-gamma-D-glutamyl-meso-diaminopimelyl-D-alanine + H(2)O = GlcNAc-MurNAc-L-alanyl-gamma-D-glutamyl-meso-diaminopimelate + D-alanine.
General function:
Involved in ATP binding
Specific function:
Reutilizes the intact tripeptide L-alanyl-gamma-D- glutamyl-meso-diaminopimelate by linking it to UDP-N-acetylmuramic acid
Gene Name:
mpl
Uniprot ID:
P37773
Molecular weight:
49874