Record Information
Version2.0
Creation Date2012-05-31 14:33:26 -0600
Update Date2015-06-03 17:19:33 -0600
Secondary Accession Numbers
  • ECMDB20212
Identification
Name:Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine
DescriptionUndecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine is an intermediate in peptidoglycan synthesis. It is a substrate for the enzyme undecaprenyldiphospho-muramoylpentapeptide beta-N-acetylglucosaminyltransferase (murG). Peptidoglycan is best described as a fisherman net. The mesh of the net is made of two segments of parallel, rather inextensible glycan threads, held together by two small elastic peptide crosslinks allowing the net to expand or shrink. The glycan moiety of the peptidoglycan is remarkably uniform among all bacteria, and is made up of alternating β-1,4-linked N-acetylglucosamine and N-acetyl muramate residues, with an average chain length (in different organisms) of 10 to 65 disaccharide units. 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-α-D-glucosamine, yielding the complete monomeric unit a lipid II, also known as lipid II. This final lipid intermediate is transferred by an as yet unknown mechanism 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. Peptide crosslinks form between different parts of the peptides depending on the organism. For example, in Mycobacteria and in E. coli most links form between the carboxyl group of the penultimate D-alanine (residue 4) of one peptide to the amino group at the D-center of meso-diaminopimelate (residue 3) of an adjacent peptide of a second glycan chain (as in E. coli). The crosslinking reaction is catalyzed by transpeptidases and involves the cleavage of the D-alanyl-D-alanine bond of the donor peptide, providing the energy to drive the reaction. As a result, the peptides in the peptidoglycan polymers are one or two amino acids shorter than the peptides in the monomers.
Structure
Thumb
Synonyms:
  • 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-alanyl-D-alanine
  • UDP-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine
  • 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-alanyl-D-alanine
  • UDP-n-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioic acid- D-alanyl-D-alanine
  • UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminoheptanedioic acid- D-alanyl-D-alanine
  • UDP-N-Acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine
  • UnPPMurNAcPentaPepNAc
Chemical Formula:C95H156N8O28P2
Weight:Average: 1920.2395
Monoisotopic: 1919.050429472
InChI Key:CEHJYQJVVYPVFY-PXJHMNRSSA-N
InChI:InChI=1S/C95H156N8O28P2/c1-58(2)30-19-31-59(3)32-20-33-60(4)34-21-35-61(5)36-22-37-62(6)38-23-39-63(7)40-24-41-64(8)42-25-43-65(9)44-26-45-66(10)46-27-47-67(11)48-28-49-68(12)54-55-125-132(121,122)131-133(123,124)130-95-82(101-74(18)107)86(85(79(57-105)128-95)129-94-81(100-73(17)106)84(111)83(110)78(56-104)127-94)126-72(16)89(114)97-70(14)88(113)102-77(52-53-80(108)109)91(116)103-76(51-29-50-75(96)93(119)120)90(115)98-69(13)87(112)99-71(15)92(117)118/h30,32,34,36,38,40,42,44,46,48,54,69-72,75-79,81-86,94-95,104-105,110-111H,19-29,31,33,35,37,39,41,43,45,47,49-53,55-57,96H2,1-18H3,(H,97,114)(H,98,115)(H,99,112)(H,100,106)(H,101,107)(H,102,113)(H,103,116)(H,108,109)(H,117,118)(H,119,120)(H,121,122)(H,123,124)/b59-32+,60-34+,61-36+,62-38+,63-40+,64-42+,65-44+,66-46+,67-48+,68-54+/t69-,70+,71-,72?,75+,76-,77-,78-,79-,81-,82-,83-,84-,85-,86-,94+,95-/m1/s1
CAS number:Not Available
IUPAC Name:(2S,6R)-2-amino-6-{[(2R)-4-carboxy-2-{[(2S)-2-[(2-{[(2R,3S,4R,5R,6R)-3-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[hydroxy({[hydroxy({[(2E,6E,10E,14E,18E,22E,26E,30E,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}-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-4-yl]oxy}-1-hydroxypropylidene)amino]-1-hydroxypropylidene]amino}-1-hydroxybutylidene]amino}-6-{[(1R)-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}hexanoic acid
Traditional IUPAC Name:(2S,6R)-2-amino-6-{[(2R)-4-carboxy-2-{[(2S)-2-[(2-{[(2R,3S,4R,5R,6R)-3-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[hydroxy({hydroxy[(2E,6E,10E,14E,18E,22E,26E,30E,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]oxyphosphoryl}oxy)phosphoryl]oxy}-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-4-yl]oxy}-1-hydroxypropylidene)amino]-1-hydroxypropylidene]amino}-1-hydroxybutylidene]amino}-6-{[(1R)-1-{[(1R)-1-carboxyethyl]-C-hydroxycarbonimidoyl}ethyl]-C-hydroxycarbonimidoyl}hexanoic acid
SMILES:OC[C@@]1([H])O[C@@]([H])(O[C@]2([H])[C@@]([H])(CO)O[C@]([H])(OP(O)(=O)OP(O)(=O)OC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CC\C([H])=C(/C)CCC=C(C)C)[C@]([H])(N=C(C)O)[C@@]2([H])OC(C)([H])C(O)=N[C@](C)([H])C(O)=N[C@]([H])(CCC(=O)O)C(O)=N[C@]([H])(CCC[C@@](N)([H])C(=O)O)C(O)=N[C@@](C)([H])C(O)=N[C@@](C)([H])C(=O)O)[C@]([H])(N=C(C)O)[C@](O)([H])[C@@]1(O)[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as polyprenyl phospho carbohydrates. These are polyprenyl phosphates with a carbohydrate moiety attached to it.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassPolyprenols
Direct ParentPolyprenyl phospho carbohydrates
Alternative Parents
Substituents
  • Polyterpenoid
  • Bactoprenol diphosphate
  • Polyprenyl phospho carbohydrate
  • Polyprenyl monophosphate
  • Polyprenyl phosphate skeleton
  • Alpha peptide
  • N-acyl-alpha-hexosamine
  • Disaccharide phosphate
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alanine or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • L-alpha-amino acid
  • Organic pyrophosphate
  • Isoprenoid phosphate
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Amino acid
  • Secondary alcohol
  • Amino acid or derivatives
  • Oxacycle
  • 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
  • Acetal
  • 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
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-5
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0055 g/LALOGPS
logP3.12ALOGPS
logP15.46ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)1.72ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count33ChemAxon
Hydrogen Donor Count17ChemAxon
Polar Surface Area586.18 ŲChemAxon
Rotatable Bond Count64ChemAxon
Refractivity513.31 m³·mol⁻¹ChemAxon
Polarizability210.69 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine + two linked disacharide pentapeptide murein units (uncrosslinked, middle of chain) > Hydrogen ion + Undecaprenyl diphosphate + three linked disacharide pentapeptide murein units (uncrosslinked, middle of chain)
2 Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine >2 Hydrogen ion +2 Undecaprenyl diphosphate + two linked disacharide pentapeptide murein units (uncrosslinked, middle of chain)
Uridine diphosphate-N-acetylglucosamine + Undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine > Hydrogen ion + Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine + Uridine 5'-diphosphate
Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine + [GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-g-D-Glu-A2pm-D-Ala-D-Ala)]n-diphosphoundecaprenol <> di-trans,poly-cis-Undecaprenyl diphosphate + [GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-g-D-Glu-A2pm-D-Ala-D-Ala)]n-diphosphoundecaprenol
Undecaprenyl-diphospho-N-acetylmuramoyl-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine + Uridine diphosphate-N-acetylglucosamine <> Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-D-glutamyl-meso-2,6-diaminopimeloyl-D-alanyl-D-alanine + Uridine 5'-diphosphate
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:
  • UDP-N-acetylmuramoyl-pentapeptide biosynthesis III (meso-DAP-containing) PWY-6387
  • peptidoglycan biosynthesis I (meso-diaminopimelate containing) PEPTIDOGLYCANSYN-PWY
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zpj-3101320497-578fe5fa257acc13d1ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-3110211943-688bc4578174b110a178View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000e-9403310822-337a1941b4fd219430aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fb9-2020001339-628372428c26ca575992View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-5600001149-4077e7b850e63bacf669View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6910002003-328c67cf306cc9213291View 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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID23724492
Kegg IDC05898
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDC1
EcoCyc IDC1

Enzymes

General function:
Involved in catalytic activity
Specific function:
Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits)
Gene Name:
mrcA
Uniprot ID:
P02918
Molecular weight:
93636
General function:
Involved in catalytic activity
Specific function:
Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits)
Gene Name:
mrcB
Uniprot ID:
P02919
Molecular weight:
94292
Reactions
(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.
General function:
Involved in penicillin binding
Specific function:
Cell wall formation. Essential for the formation of a septum of the murein sacculus. Synthesis of cross-linked peptidoglycan from the lipid intermediates
Gene Name:
ftsI
Uniprot ID:
P0AD68
Molecular weight:
63877
Reactions
(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.
General function:
Involved in undecaprenyldiphospho-muramoylpentapeptide beta-N-acetylglucosaminyltransferase activity
Specific function:
Cell wall formation. Catalyzes the transfer of a GlcNAc subunit on undecaprenyl-pyrophosphoryl-MurNAc-pentapeptide (lipid intermediate I) to form undecaprenyl-pyrophosphoryl-MurNAc- (pentapeptide)GlcNAc (lipid intermediate II)
Gene Name:
murG
Uniprot ID:
P17443
Molecular weight:
37815
Reactions
UDP-N-acetylglucosamine + Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol = UDP + GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol.
General function:
Involved in catalytic activity
Specific function:
Cell wall formation. The enzyme has a penicillin- insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a transpeptidase C-terminal domain which may not be functional
Gene Name:
pbpC
Uniprot ID:
P76577
Molecular weight:
85066
General function:
Involved in lipid transporter activity
Specific function:
Specific function unknown
Gene Name:
mviN
Uniprot ID:
P0AF16
Molecular weight:
55267

Transporters

General function:
Involved in lipid transporter activity
Specific function:
Specific function unknown
Gene Name:
mviN
Uniprot ID:
P0AF16
Molecular weight:
55267