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UDP-N-Acetylmuramoyl-L-alanyl-gamma-D-glutamyl-L-lysine (M2MDB001052)

Record Information
Version2.0
Creation Date2012-05-31 14:33:07 -0600
Update Date2015-06-03 17:19:32 -0600
Secondary Accession Numbers
  • ECMDB20206
Identification
Name:UDP-N-Acetylmuramoyl-L-alanyl-gamma-D-glutamyl-L-lysine
DescriptionUDP-N-acetylmuramoyl-L-alanyl-gamma-D-glutamyl-L-lysine 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
MOLSDFPDBSMILESInChI
Synonyms:
  • UDP-N-Acetylmuramoyl-L-alanyl-D-g-glutamyl-L-lysine
  • UDP-N-Acetylmuramoyl-L-alanyl-D-gamma-glutamyl-L-lysine
  • UDP-N-Acetylmuramoyl-L-alanyl-D-γ-glutamyl-L-lysine
  • UDP-N-Acetylmuramoyl-L-alanyl-g-D-glutamyl-L-lysine
  • UDP-N-Acetylmuramoyl-L-alanyl-γ-D-glutamyl-L-lysine
  • Udpmurac(oyl-L-ala-D-g-glu-L-lys)
  • Udpmurac(oyl-L-ala-D-gamma-glu-L-LYS)
  • Udpmurac(oyl-L-ala-D-γ-glu-L-lys)
Chemical Formula:C34H55N7O24P2
Weight:Average: 1007.7805
Monoisotopic: 1007.277368747
InChI Key:WXBLSQNZKMJACT-BYEZXYKXSA-N
InChI:InChI=1S/C34H55N7O24P2/c1-14(28(49)39-18(32(53)54)7-8-21(44)38-17(31(51)52)6-4-5-10-35)36-29(50)15(2)61-27-23(37-16(3)43)33(63-19(12-42)25(27)47)64-67(58,59)65-66(56,57)60-13-20-24(46)26(48)30(62-20)41-11-9-22(45)40-34(41)55/h9,11,14-15,17-20,23-27,30,33,42,46-48H,4-8,10,12-13,35H2,1-3H3,(H,36,50)(H,37,43)(H,38,44)(H,39,49)(H,51,52)(H,53,54)(H,56,57)(H,58,59)(H,40,45,55)/t14-,15+,17-,18+,19+,20+,23+,24+,25+,26+,27+,30+,33+/m0/s1
CAS number:Not Available
IUPAC Name:(2S)-6-amino-2-{[(4R)-4-carboxy-4-{[(2S)-2-{[(2R)-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}hexanoic acid
Traditional IUPAC Name:(2S)-6-amino-2-{[(4R)-4-carboxy-4-{[(2S)-2-{[(2R)-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}hexanoic acid
SMILES:[H][C@](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)=N[C@@]([H])(C)C(O)=N[C@]([H])(CCC(O)=N[C@@]([H])(CCCCN)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
  • Saccharolipid
  • 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
  • Monosaccharide phosphate
  • N-substituted-alpha-amino acid
  • Organic pyrophosphate
  • Alpha-amino acid or derivatives
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Monoalkyl phosphate
  • Amino fatty acid
  • Pyrimidone
  • Fatty amide
  • Dicarboxylic acid or derivatives
  • Hydropyrimidine
  • Monosaccharide
  • N-acyl-amine
  • Alkyl phosphate
  • Organic phosphoric acid derivative
  • Oxane
  • Fatty acid
  • Phosphoric acid ester
  • Fatty acyl
  • Pyrimidine
  • Acetamide
  • Tetrahydrofuran
  • Vinylogous amide
  • Heteroaromatic compound
  • Secondary alcohol
  • Amino acid or derivatives
  • Urea
  • Amino acid
  • Lactam
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Oxacycle
  • Carboxylic acid
  • Dialkyl ether
  • Organoheterocyclic compound
  • Ether
  • Primary amine
  • Organic oxygen compound
  • Alcohol
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxide
  • Organonitrogen compound
  • Amine
  • Organooxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility2.11 g/LALOGPS
logP-0.71ALOGPS
logP-4.3ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)1.71ChemAxon
pKa (Strongest Basic)10.21ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count27ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area494.78 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity215.29 m³·mol⁻¹ChemAxon
Polarizability91.66 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-gamma-D-glutamyl-L-lysine + D-Alanyl-D-alanine <> ADP + Phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
Adenosine triphosphate + UDP-N-Acetylmuramoyl-L-alanyl-gamma-D-glutamyl-L-lysine + D-Alanyl-D-alanine > ADP + Inorganic phosphate + UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-L-lysyl-D-alanyl-D-alanine
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-0912000002-0a9d4fb42f1504b1854bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2911000000-f00c3a3284470a97c529View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-3921000000-8e8baadea2472697176cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dr-9803330047-46de92d90a5f4b535242View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03el-6915110606-d574100562f4eb546e63View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06tf-4913100000-5d9444a83771be143fd3View in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView 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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16329
HMDB IDNot Available
Pubchem Compound ID5462297
Kegg IDC05892
ChemSpider ID4575364
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase
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.