Record Information
Version2.0
Creation Date2012-10-10 12:12:59 -0600
Update Date2015-06-03 17:25:45 -0600
Secondary Accession Numbers
  • ECMDB23024
Identification
Name:GlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol
DescriptionGlcNAc-(1->4)-Mur2Ac(oyl-L-Ala-gamma-D-Glu-L-Lys-D-Ala-D-Ala)-diphosphoundecaprenol is an intermediate in peptidoglycan synthesis. It is a substrate for peptidoglycan glycosyltransferase (EC 2.4.1.129) which catalyzes the chemical reaction [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.
Structure
Thumb
Synonyms:
  • (2R)-2-(2S)-2-(2R)-2-(2R,3R,4R,5S,6R)-3-acetamido-5-(2S,3R,4R,5S,6R)-3-acetamido-4,5-Dihydroxy-6-(hydroxymethyl)oxan-2-yloxy-2-hydroxy-hydroxy-(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,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-undecaenoxyphosphoryloxyphosphoryloxy-6-(hydroxymethyl)oxan-4-yloxypropanoylaminopropanoylamino-5-(2S)-6-amino-1-(2R)-1-(1R)-1-carboxyethylamino-1-oxopropan-2-ylamino-1-oxohexan-2-ylamino-5-oxopentanoate
  • (2R)-2-(2S)-2-(2R)-2-(2R,3R,4R,5S,6R)-3-acetamido-5-(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yloxy-2-hydroxy-hydroxy-(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,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-undecaenoxyphosphoryloxyphosphoryloxy-6-(hydroxymethyl)oxan-4-yloxypropanoylaminopropanoylamino-5-(2S)-6-amino-1-(2R)-1-(1R)-1-carboxyethylamino-1-oxopropan-2-ylamino-1-oxohexan-2-ylamino-5-oxopentanoic acid
  • (2R,5R,8S,13R,16S,19R)-19-{(2R,3R,4R,5S,6R)-3-acetamido-5-{(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy}-2-({hydroxy(hydroxy{(2Z,6Z,10Z,14Z,18Z,22Z,26Z, 30Z,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecaen-1-yloxy}phosphoryl)oxyphosphoryl}oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yloxy}-8 -(4-aminobutyl)-13-carboxy-2,5,16-trimethyl-4,7,10,15,18-pentaoxo-3,6,9,14,17-pentaazaicosan-1-Oate (N
  • (2R,5R,8S,13R,16S,19R)-19-{(2R,3R,4R,5S,6R)-3-Acetamido-5-{(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy}-2-({hydroxy(hydroxy{(2Z,6Z,10Z,14Z,18Z,22Z,26Z, 30Z,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecaen-1-yloxy}phosphoryl)oxyphosphoryl}oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yloxy}-8 -(4-aminobutyl)-13-carboxy-2,5,16-trimethyl-4,7,10,15,18-pentaoxo-3,6,9,14,17-pentaazaicosan-1-oic acid (n
  • GlcNAc-(1->4)-mur2ac(oyl-L-ala-g-D-glu-L-lys-D-ala-D-ala)-diphosphoundecaprenol
  • GlcNAc-(1->4)-mur2ac(oyl-L-ala-γ-D-glu-L-lys-D-ala-D-ala)-diphosphoundecaprenol
  • Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-g-D-glutamyl-L-lysyl-D-alanyl-D-alanine
  • Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-gamma-D-glutamyl-L-lysyl-D-alanyl-D-alanine
  • Undecaprenyl-diphospho-N-acetylmuramoyl-(N-acetylglucosamine)-L-alanyl-γ-D-glutamyl-L-lysyl-D-alanyl-D-alanine
  • undecaprenyldiphospho-N-Acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-D-g-glutamyl-L-lysyl-D-alanyl-D-alanine
  • Undecaprenyldiphospho-N-acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-D-gamma-glutamyl-L-lysyl-D-alanyl-D-alanine
  • undecaprenyldiphospho-N-Acetyl-(N-acetylglucosaminyl)muramoyl-L-alanyl-D-γ-glutamyl-L-lysyl-D-alanyl-D-alanine
Chemical Formula:C94H156N8O26P2
Weight:Average: 1876.23
Monoisotopic: 1875.060600228
InChI Key:ULXTYUPMJXVUHQ-OVTFQNCVSA-N
InChI:InChI=1S/C94H156N8O26P2/c1-59(2)31-21-32-60(3)33-22-34-61(4)35-23-36-62(5)37-24-38-63(6)39-25-40-64(7)41-26-42-65(8)43-27-44-66(9)45-28-46-67(10)47-29-48-68(11)49-30-50-69(12)54-56-122-129(118,119)128-130(120,121)127-94-82(100-75(18)106)86(85(79(58-104)125-94)126-93-81(99-74(17)105)84(109)83(108)78(57-103)124-93)123-73(16)89(112)96-71(14)88(111)102-77(92(116)117)52-53-80(107)101-76(51-19-20-55-95)90(113)97-70(13)87(110)98-72(15)91(114)115/h31,33,35,37,39,41,43,45,47,49,54,70-73,76-79,81-86,93-94,103-104,108-109H,19-30,32,34,36,38,40,42,44,46,48,50-53,55-58,95H2,1-18H3,(H,96,112)(H,97,113)(H,98,110)(H,99,105)(H,100,106)(H,101,107)(H,102,111)(H,114,115)(H,116,117)(H,118,119)(H,120,121)/b60-33+,61-35+,62-37-,63-39-,64-41-,65-43-,66-45-,67-47-,68-49-,69-54-/t70-,71+,72-,73-,76+,77-,78-,79-,81-,82-,83-,84-,85-,86-,93+,94-/m1/s1
CAS number:Not Available
IUPAC Name:(2R)-4-{[(1S)-5-amino-1-{[(1R)-1-{[(1R)-1-carboxyethyl]carbamoyl}ethyl]carbamoyl}pentyl]carbamoyl}-2-[(2S)-2-[(2R)-2-{[(2R,3R,4R,5S,6R)-3-acetamido-5-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-{[hydroxy({[hydroxy({[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,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}-6-(hydroxymethyl)oxan-4-yl]oxy}propanamido]propanamido]butanoic acid
Traditional IUPAC Name:lipid II
SMILES:NCCCC[C@H](NC(=O)CC[C@@H](NC(=O)[C@H](C)NC(=O)[C@@H](C)O[C@H]1[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2NC(C)=O)[C@@H](CO)O[C@H](OP(O)(=O)OP(O)(=O)OC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(\C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)[C@@H]1NC(C)=O)C(O)=O)C(=O)N[C@H](C)C(=O)N[C@H](C)C(O)=O
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
  • Polyprenyl phospho carbohydrate
  • Bactoprenol diphosphate
  • Alpha-oligopeptide
  • Polyprenyl monophosphate
  • Polyprenyl phosphate skeleton
  • Alpha peptide
  • Disaccharide phosphate
  • N-acyl-alpha-hexosamine
  • Glutamine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alanine or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Isoprenoid phosphate
  • Organic pyrophosphate
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Monoalkyl phosphate
  • N-acyl-amine
  • Fatty acyl
  • Alkyl phosphate
  • Organic phosphoric acid derivative
  • Fatty amide
  • Oxane
  • Dicarboxylic acid or derivatives
  • Phosphoric acid ester
  • Acetamide
  • Amino acid
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Dialkyl ether
  • Acetal
  • Ether
  • Organic oxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxide
  • Primary alcohol
  • Organic nitrogen compound
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Primary aliphatic amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
  • undecaprenyldiphospho-N-acetylmuramoyl peptide (CHEBI:27692 )
  • Bactoprenol diphosphates (C05893 )
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0031 g/LALOGPS
logP3.23ALOGPS
logP8.79ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)1.71ChemAxon
pKa (Strongest Basic)10.19ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count24ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area524.45 ŲChemAxon
Rotatable Bond Count63ChemAxon
Refractivity503.83 m³·mol⁻¹ChemAxon
Polarizability202.75 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:Not Available
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID27692
HMDB IDNot Available
Pubchem Compound ID46173749
Kegg IDC05893
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

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:
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.