P. aeruginosa Metabolome Database: 1,6-Anhydrous-N-Acetylmuramyl-tetrapeptide (PAMDB001520)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB001520

Identification

Name:

1,6-Anhydrous-N-Acetylmuramyl-tetrapeptide

Description:

1,6-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

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

Not Available

Chemical Formula:

C₂₉H₄₈N₆O₁₅

Average Molecular Weight:

720.7226

Monoisotopic Molecular Weight:

720.317764896

InChI Key:

OUWAMZWZTFUVMV-NPLPHQDTSA-N

InChI:

InChI=1S/C29H48N6O15/c1-12(31-25(42)14(3)50-23-19(33-15(4)37)11-49-20(10-36)22(23)40)24(41)34-18(8-9-21(38)39)27(44)35-17(7-5-6-16(30)29(47)48)26(43)32-13(2)28(45)46/h12-14,16-20,22-23,36,40H,5-11,30H2,1-4H3,(H,31,42)(H,32,43)(H,33,37)(H,34,41)(H,35,44)(H,38,39)(H,45,46)(H,47,48)/t12-,13?,14+,16?,17-,18+,19-,20+,22+,23+/m0/s1

CAS number:

Not Available

IUPAC Name:

(6S)-2-amino-6-{[(2R)-4-carboxy-1-hydroxy-2-{[(2S)-1-hydroxy-2-{[(2R)-1-hydroxy-2-{[(2R,3S,4R,5S)-3-hydroxy-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)oxan-4-yl]oxy}propylidene]amino}propylidene]amino}butylidene]amino}-6-[(1-carboxyethyl)-C-hydroxycarbonimidoyl]hexanoic acid

Traditional IUPAC Name:

SMILES:

[H]C(N)(CCC[C@]([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@@]([H])(CO)OC[C@]1([H])N=C(C)O)C(O)=NC([H])(C)C(O)=O)C(O)=O

Chemical Taxonomy

Taxonomy Description

This 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 Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Substituents

Alpha peptide
N-acyl-aliphatic-alpha amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Glucosamine
Amino sugar
Alpha-amino acid or derivatives
Alpha-amino acid
Tricarboxylic acid or derivatives
Amino saccharide
Amino fatty acid
Fatty acyl
Oxane
Monosaccharide
Saccharide
Secondary alcohol
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
Hydrocarbon derivative
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.119 mg/mL	ALOGPS
logP	-1.6	ALOGPS
logP	-3.4	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	1.74	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	359.79 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	167.06 m³·mol^-1	ChemAxon
Polarizability	71.19 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

1,6-Anhydrous-N-Acetylmuramyl-tetrapeptide + Water > L-Alanine-D-glutamate-meso-2,6-diaminoheptanedioate-D-alanine + 1,6-Anhydro-N-acetylmuramate
N-Acetyl-D-glucosamine(anhydrous)N-Acetylmuramyl-tetrapeptide + Water > N-Acetyl-D-glucosamine + 1,6-Anhydrous-N-Acetylmuramyl-tetrapeptide
1,6-Anhydrous-N-Acetylmuramyl-tetrapeptide + Water > D-Alanine + 1,6-Anhydrous-N-Acetylmuramyl-tripeptide

Pathways:

D-Alanine metabolism pae00473

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0w29-2024609600-5c06d74269d2175108e8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0w2i-5169204100-4047e1d075d03de181e6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gw3-9758410000-e8e478de24b750f6f262	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0400-2010129400-188601d3d46bca2c6f7f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-4051329500-eedef7ae7b54f205361f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0zg0-9161011000-cb1c1116bf3a10740b7b	View in MoNA

References

References:

Not Available

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	Not Available
HMDB ID	Not Available
Pubchem Compound ID	46173341
Kegg ID	Not Available
ChemSpider ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	CPD0-2285
EcoCyc ID	CPD0-2285

1,6-Anhydrous-N-Acetylmuramyl-tetrapeptide (PAMDB001520)

Structure for 1,6-Anhydrous-N-Acetylmuramyl-tetrapeptide (PAMDB001520)