Record Information
Version2.0
Creation Date2012-07-30 14:55:05 -0600
Update Date2015-06-03 17:20:59 -0600
Secondary Accession Numbers
  • ECMDB21241
Identification
Name:L-Alanyl-D-glutamate
Description:L-alanine-D-glutamate is a dipeptide. 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 dipeptide that is a component of the bacterial cell wall. It is a substrate of Alanyl-glutamate epimerase which catalyzes the epimerization of L-Ala-D-Glu to L-Ala-L- Glu and has a role in the recycling of the murein peptide, of which L-Ala-D-Glu is a component. This enzyme also able to catalyze the reverse reaction.
Structure
Thumb
Synonyms:
  • L-Ala-γ-D-Glu
  • L-Ala-g-D-glu
  • L-Ala-gamma-D-Glu
  • L-Ala-γ-D-glu
  • L-alanine-D-glutamate
  • L-Alanine-D-glutamic acid
  • L-Alanyl-D-glutamic acid
Chemical Formula:C8H13N2O5
Weight:Average: 217.1992
Monoisotopic: 217.082446536
InChI Key:VYZAGTDAHUIRQA-UHFFFAOYSA-M
InChI:InChI=1S/C8H14N2O5/c1-4(9)7(13)10-5(8(14)15)2-3-6(11)12/h4-5H,2-3,9H2,1H3,(H,10,13)(H,11,12)(H,14,15)/p-1
CAS number:Not Available
IUPAC Name:4-[(2-amino-1-hydroxypropylidene)amino]-4-carboxybutanoate
Traditional IUPAC Name:4-[(2-amino-1-hydroxypropylidene)amino]-4-carboxybutanoate
SMILES:CC(N)C(O)=NC(CCC([O-])=O)C(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Glutamic acid or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alanine or derivatives
  • Alpha-amino acid or derivatives
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Primary amine
  • Amine
  • Hydrocarbon derivative
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility11.7 mg/mLALOGPS
logP-3.1ALOGPS
logP-3.2ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.58ChemAxon
pKa (Strongest Basic)9.57ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area136.04 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity59.94 m3·mol-1ChemAxon
Polarizability20.34 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-2090000000-7c785bd03809c13953e8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9110000000-02737abc6d23cae13de3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-4b2f85d956a4fd192b98View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1190000000-ab19bb69614d900386a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-7290000000-6ceb7509f287b97356abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9000000000-a7ebfca0baaa5806c21aView in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID61395
HMDB IDHMDB28686
Pubchem Compound ID25203551
Kegg IDNot Available
ChemSpider ID13211968
Wikipedia IDNot Available
BioCyc IDCPD0-2190
EcoCyc IDCPD0-2190

Enzymes

General function:
Involved in cellular amino acid catabolic process
Specific function:
Catalyzes the epimerization of L-Ala-D-Glu to L-Ala-L- Glu and has a role in the recycling of the murein peptide, of which L-Ala-D-Glu is a component. Is also able to catalyze the reverse reaction and the epimerization of all the L-Ala-X dipeptides, except L-Ala-L-Arg, L-Ala-L-Lys and L-Ala-L-Pro. Is also active with L-Gly-L-Glu, L-Phe-L-Glu, and L-Ser-L-Glu, but not with L-Glu-L-Glu, L-Lys-L-Glu, L-Pro-L-Glu, L-Lys-L-Ala, or D- Ala-D-Ala
Gene Name:
ycjG
Uniprot ID:
P51981
Molecular weight:
34674
Reactions
L-alanyl-D-glutamate = L-alanyl-L-glutamate.
General function:
Involved in metallocarboxypeptidase activity
Specific function:
Specific function unknown
Gene Name:
mpaA
Uniprot ID:
P0ACV6
Molecular weight:
26558

Transporters

General function:
Involved in peptide transporter activity
Specific function:
Proton-dependent permease that transports di- and tripeptides. Has a clear preference for dipeptides and tripeptides composed of L-amino acids, and discriminates dipeptides on the basis of the position of charges within the substrate
Gene Name:
dtpB
Uniprot ID:
P36837
Molecular weight:
53575
General function:
Involved in peptide transporter activity
Specific function:
Probable proton-dependent permease that transports di- and tripeptides. Shows significantly higher specificity towards dipeptides
Gene Name:
yjdL
Uniprot ID:
P39276
Molecular weight:
53054
General function:
Involved in peptide transporter activity
Specific function:
Probable proton-dependent permease that transports dipeptides
Gene Name:
dtpD
Uniprot ID:
P75742
Molecular weight:
54158
General function:
Involved in peptide transporter activity
Specific function:
Proton-dependent permease that transports di- and tripeptides as well as structurally related peptidomimetics such as aminocephalosporins into the cell. Has a clear preference for dipeptides and tripeptides composed of L-amino acids, and discriminates dipeptides on the basis of the position of charges within the substrate
Gene Name:
dtpA
Uniprot ID:
P77304
Molecular weight:
53991
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368