N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tetrapeptide (PAMDB001657)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB001657
Identification
Name: N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tetrapeptide
Description:N-acetyl-D-glucosamine(anhydrous)N-acetylmuramyl-tetrapeptide is an intermediate in peptidoglycan synthesis and turnover. Peptidoglycan can be described as a fisherman's net that encloses bacteria. The mesh of the net is made of two segments of parallel, somewhat 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 very 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 lengthof 10 to 65 disaccharide units (depending on the organism). The peptidoglycan synthesis pathway starts in 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 Pseudomonas aeruginosa 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 Pseudomonas aeruginosa). 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
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:Not Available
Chemical Formula: C37H59N7O20
Average Molecular Weight: 921.8993
Monoisotopic Molecular Weight: 921.381487363
InChI Key: ZTOWCORYLXDAAW-JOUWMGDHSA-N
InChI:InChI=1S/C37H59N7O20/c1-13(30(52)43-20(9-10-23(48)49)33(55)44-19(8-6-7-18(38)35(58)59)32(54)40-14(2)34(56)57)39-31(53)15(3)61-29-25(42-17(5)47)36-60-12-22(63-36)28(29)64-37-24(41-16(4)46)27(51)26(50)21(11-45)62-37/h13-15,18-22,24-29,36-37,45,50-51H,6-12,38H2,1-5H3,(H,39,53)(H,40,54)(H,41,46)(H,42,47)(H,43,52)(H,44,55)(H,48,49)(H,56,57)(H,58,59)/t13?,14?,15?,18?,19?,20?,21-,22?,24-,25-,26-,27-,28?,29-,36?,37+/m1/s1
CAS number: Not Available
IUPAC Name:2-amino-6-{[4-carboxy-2-({2-[(2-{[(3R,4R)-2-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-4-[(1-hydroxyethylidene)amino]-6,8-dioxabicyclo[3.2.1]octan-3-yl]oxy}-1-hydroxypropylidene)amino]-1-hydroxypropylidene}amino)-1-hydroxybutylidene]amino}-6-[(1-carboxyethyl)-C-hydroxycarbonimidoyl]hexanoic acid
Traditional IUPAC Name: 2-amino-6-{[4-carboxy-2-({2-[(2-{[(3R,4R)-2-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-4-[(1-hydroxyethylidene)amino]-6,8-dioxabicyclo[3.2.1]octan-3-yl]oxy}-1-hydroxypropylidene)amino]-1-hydroxypropylidene}amino)-1-hydroxybutylidene]amino}-6-[(1-carboxyethyl)-C-hydroxycarbonimidoyl]hexanoic acid
SMILES:[H]C(N)(CCCC([H])(N=C(O)C([H])(CCC(O)=O)N=C(O)C([H])(C)N=C(O)C([H])(C)O[C@@]1([H])C([H])(O[C@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])N=C(C)O)C2([H])COC([H])(O2)[C@]1([H])N=C(C)O)C(O)=NC([H])(C)C(O)=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds 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.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent Peptides
Alternative Parents
Substituents
  • Alpha peptide
  • Saccharolipid
  • N-acyl-alpha-hexosamine
  • N-acyl-aliphatic-alpha amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Glucosamine
  • Amino sugar
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Alpha-amino acid or derivatives
  • Alpha-amino acid
  • Tricarboxylic acid or derivatives
  • Amino saccharide
  • Oxepane
  • Amino fatty acid
  • Fatty acyl
  • Oxane
  • Meta-dioxolane
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Ether
  • Dialkyl ether
  • Carboxylic acid
  • Carboximidic acid derivative
  • Carboximidic acid
  • Acetal
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular Framework Aliphatic heteropolycyclic compounds
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:-3
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.273 mg/mLALOGPS
logP-1.3ALOGPS
logP-1.5ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)3.27ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count27ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area440.3 Å2ChemAxon
Rotatable Bond Count24ChemAxon
Refractivity208.61 m3·mol-1ChemAxon
Polarizability88.32 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
two linked disacharide tetrapeptide and tripeptide murein units (uncrosslinked, middle of chain) > N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tripeptide + N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tetrapeptide
N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tetrapeptide + Water > L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine + N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramic acid
two linked disacharide tetrapeptide murein units (uncrosslinked, middle of chain) >2 N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tetrapeptide
three disacharide linked murein units (tetrapeptide crosslinked tetrapeptide (A2pm->D-ala), one uncrosslinked tetrapaptide) (middle of chain) > N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tetrapeptide + two disacharide linked murein units, tetrapeptide corsslinked tetrapeptide (A2pm->D-ala) (middle of chain)
N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tetrapeptide + Water > N-Acetyl-D-glucosamine + 1,6-Anhydrous-N-Acetylmuramyl-tetrapeptide
N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tetrapeptide + Water > D-Alanine + N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tripeptide
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0w29-1021520096-9f9738393d1e47f52d94View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w29-7198575262-e939bdb5e333fe1d42c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gw3-9777321121-eb2e6423a589f8905a97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0is0-5100202595-ec719bc646cb79c60c5fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0w4i-3021102494-1621d93bf5ac223053d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06s9-9183344000-5e2bd876f0130292b947View in MoNA
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID45479403
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDCPD0-2292
EcoCyc IDCPD0-2292

Enzymes

Protein Details
• N-acetylmuramoyl-L-alanine amidase AmiB
General function:
Involved in N-acetylmuramoyl-L-alanine amidase activity
Specific function:
Cell-wall hydrolase probably involved in cell-wall hydrolysis, septation or recycling
Gene Name:
amiB
Locus Tag:
PA4947
Molecular weight:
50.7 kDa
Reactions
Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides.
Protein Details
• Probable N-acetylmuramoyl-L-alanine amidase AmiA
General function:
Involved in N-acetylmuramoyl-L-alanine amidase activity
Specific function:
Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides
Gene Name:
amiA
Locus Tag:
PA5538
Molecular weight:
42.9 kDa
Reactions
Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides.
Protein Details
• N-acetylmuramoyl-L-alanine amidase AmiC
General function:
Involved in N-acetylmuramoyl-L-alanine amidase activity
Specific function:
Cell-wall hydrolase probably involved in cell-wall hydrolysis, septation or recycling
Gene Name:
amiC
Locus Tag:
PA3364
Molecular weight:
42.8 kDa
Reactions
Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides.
Protein Details
• Beta-hexosaminidase
General function:
Involved in beta-N-acetylhexosaminidase activity
Specific function:
Cleaves GlcNAc linked beta-1,4 to MurNAc tripeptides
Gene Name:
nagZ
Locus Tag:
PA3005
Molecular weight:
36.1 kDa
Reactions
Hydrolysis of terminal non-reducing N-acetyl-D-hexosamine residues in N-acetyl-beta-D-hexosaminides.
Protein Details
• Murein tetrapeptide carboxypeptidase
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
Locus Tag:
PA1818
Molecular weight:
82.8 kDa
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.
Protein Details
• Membrane-bound lytic murein transglycosylase B
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Murein-degrading enzyme. Catalyzes the cleavage of the glycosidic bonds between N-acetylmuramic acid and N- acetylglucosamine residues in peptidoglycan. May play a role in recycling of muropeptides during cell elongation and/or cell division
Gene Name:
mltB
Locus Tag:
PA4444
Molecular weight:
41.4 kDa
Reactions
Exolytic cleavage of the (1->4)-beta-glycosidic linkage between N-acetylmuramic acid (MurNAc) and N-acetylglucosamine (GlcNAc) residues in peptidoglycan, from either the reducing or the non-reducing ends of the peptidoglycan chains, with concomitant formation of a 1,6-anhydrobond in the MurNAc residue.
Protein Details
• 1,6-anhydro-N-acetylmuramyl-L-alanine amidase AmpD
General function:
Involved in N-acetylmuramoyl-L-alanine amidase activity
Specific function:
Involved in both cell wall peptidoglycans recycling and beta-lactamase induction. Specifically cleaves the amide bond between the lactyl group of N-acetylmuramic acid and the alpha- amino group of the L-alanine in degradation products containing an anhydro N-acetylmuramyl moiety
Gene Name:
ampD
Locus Tag:
PA4522
Molecular weight:
21 kDa
Reactions
Hydrolyzes the link between N-acetylmuramoyl residues and L-amino acid residues in certain cell-wall glycopeptides.

Transporters