Record Information
Version2.0
Creation Date2012-05-31 14:33:04 -0600
Update Date2015-06-03 17:19:32 -0600
Secondary Accession Numbers
  • ECMDB20205
Identification
Name:UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
DescriptionUDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine 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. UDP-MurNAc-pentapeptide is a peptidoglycan precursor. 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. UDP-MurNAc-pentapeptide is a feedback inhibitor of UDP-MurNAc-peptide synthesis. (PMID 357424)
Structure
Thumb
Synonyms:
  • UDP-Mur2Ac(oyl-L-Ala-g-D-Glu-L-Lys-D-Ala-D-Ala)
  • UDP-MurNAc-pentapeptide
  • UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
  • UDP-N-Acetylmuramoyl-L-alanyl-g-D-glutamyl-L-lysyl-D-alanyl-D-alanine
  • UDP-N-Acetylmuramoyl-L-alanyl-gamma-D-glutamyl-L-lysyl-D-alanyl-D-alanine
  • UDP-N-Acetylmuramoyl-L-alanyl-γ-D-glutamyl-L-lysyl-D-alanyl-D-alanine
  • Udpmurac(oyl-L-ala-D-g-glu-L-lys-D-ala-D-ala)
  • Udpmurac(oyl-L-ala-D-gamma-glu-L-LYS-D-ala-D-ala)
  • Udpmurac(oyl-L-ala-D-γ-glu-L-lys-D-ala-D-ala)
Chemical Formula:C40H65N9O26P2
Weight:Average: 1149.9363
Monoisotopic: 1149.351596321
InChI Key:PFMVORMCVGOQKR-FQSOPKRZSA-N
InChI:InChI=1S/C40H65N9O26P2/c1-16(32(57)44-18(3)37(61)62)43-35(60)21(8-6-7-12-41)46-25(52)10-9-22(38(63)64)47-33(58)17(2)42-34(59)19(4)71-31-27(45-20(5)51)39(73-23(14-50)29(31)55)74-77(68,69)75-76(66,67)70-15-24-28(54)30(56)36(72-24)49-13-11-26(53)48-40(49)65/h11,13,16-19,21-24,27-31,36,39,50,54-56H,6-10,12,14-15,41H2,1-5H3,(H,42,59)(H,43,60)(H,44,57)(H,45,51)(H,46,52)(H,47,58)(H,61,62)(H,63,64)(H,66,67)(H,68,69)(H,48,53,65)/t16-,17+,18-,19?,21+,22?,23-,24-,27-,28-,29-,30-,31-,36-,39?/m1/s1
CAS number:Not Available
IUPAC Name:4-{[(1S)-5-amino-1-{[(1R)-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}pentyl]-C-hydroxycarbonimidoyl}-2-{[(2S)-2-[(2-{[(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}butanoic acid
Traditional IUPAC Name:4-{[(1S)-5-amino-1-{[(1R)-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}pentyl]-C-hydroxycarbonimidoyl}-2-{[(2S)-2-[(2-{[(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}butanoic acid
SMILES:[H]C(C)(O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO)OC([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)=N[C@@]([H])(C)C(O)=NC([H])(CCC(O)=N[C@@]([H])(CCCCN)C(O)=N[C@]([H])(C)C(O)=N[C@]([H])(C)C(O)=O)C(O)=O
Chemical Taxonomy
ClassificationNot classified
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.2 g/LALOGPS
logP-0.38ALOGPS
logP-3.7ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)1.71ChemAxon
pKa (Strongest Basic)10.21ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count31ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area559.96 ŲChemAxon
Rotatable Bond Count30ChemAxon
Refractivity250.93 m³·mol⁻¹ChemAxon
Polarizability106.12 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Lysine biosynthesisPW000771 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-1900100000-ca60f48eab121e478fd8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3900000100-5f1cabf69b348c6629aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-6921100001-9b4fc4ff9dae58b61f10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03e9-5901100100-e2f2c32dccc7d77d95a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001l-4903100002-39705f2f3e29d8e03294View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bvl-4913011000-3d8817522bb28cc942c2View in MoNA
References
References:
  • Ishiguro, E. E., Ramey, W. D. (1978). "Involvement of the relA gene product and feedback inhibition in the regulation of DUP-N-acetylmuramyl-peptide synthesis in Escherichia coli." J Bacteriol 135:766-774. Pubmed: 357424
  • 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
  • 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
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID17277
HMDB IDNot Available
Pubchem Compound ID440448
Kegg IDC04702
ChemSpider ID389383
Wikipedia IDNot Available
BioCyc IDC3
EcoCyc IDC3

Enzymes

General function:
Involved in phospho-N-acetylmuramoyl-pentapeptide-transferase activity
Specific function:
First step of the lipid cycle reactions in the biosynthesis of the cell wall peptidoglycan
Gene Name:
mraY
Uniprot ID:
P0A6W3
Molecular weight:
39875
Reactions
UDP-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala) + undecaprenyl phosphate = UMP + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol.
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.