ECMDB: L-Ala-gamma-D-Glu (ECMDB20574) (M2MDB001377)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (2)XML

Proteins (2)

Record Information

Version

2.0

Creation Date

2012-05-31 14:51:22 -0600

Update Date

2015-06-03 17:20:19 -0600

Secondary Accession Numbers

ECMDB20574

Identification

Name:

L-Ala-gamma-D-Glu

Description

L-ala-gamma-D-glu is a member of the chemical class known as Hybrid Peptides. These are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta). UDPMurNAc-L-Ala-gamma-D-Glu-X-D-Ala-DAla (X = L-Lys or m-DAP) is the cytoplasmic precursor for the lipid-linked cycle of bacterial peptidoglycan biosynthesis, consisting of at least four enzymatic reactions, which are targets for antibacterial agents. (PMID 17216029)

Structure

MOL SDF PDB SMILES InChI

Synonyms:

L-Ala-γ-D-Glu
L-Ala-g-D-glu
L-Ala-γ-D-glu
L-Alanine-D-glutamate
L-Alanine-D-glutamic acid

Chemical Formula:

C₈H₁₃N₂O₅

Weight:

Average: 217.1992
Monoisotopic: 217.082446536

InChI Key:

VYZAGTDAHUIRQA-CRCLSJGQSA-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/t4-,5+/m0/s1

CAS number:

Not Available

IUPAC Name:

(4R)-4-{[(2S)-2-amino-1-hydroxypropylidene]amino}-4-carboxybutanoate

Traditional IUPAC Name:

(4R)-4-{[(2S)-2-amino-1-hydroxypropylidene]amino}-4-carboxybutanoate

SMILES:

[H][C@@](C)(N)C(O)=N[C@]([H])(CCC([O-])=O)C(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

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
Carboxylic acid salt
Amino acid
Secondary carboxylic acid amide
Carboxylic acid
Organooxygen compound
Organonitrogen compound
Amine
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Primary amine
Organic salt
Hydrocarbon derivative
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

peptide anion (CHEBI:61395 )

Physical Properties

State:

Not Available

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	11.7 g/L	ALOGPS
logP	-3.1	ALOGPS
logP	-3.2	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	3.58	ChemAxon
pKa (Strongest Basic)	9.57	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	136.04 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	59.94 m³·mol⁻¹	ChemAxon
Polarizability	20.21 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	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:

L-Ala-gamma-D-Glu-Dap + Water > L-Ala-gamma-D-Glu + <i>meso</i>-diaminopimelate
L-Ala-gamma-D-Glu L-Alanyl-L-Glutamate

SMPDB Pathways:

Not Available

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-2090000000-7c785bd03809c13953e8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9110000000-02737abc6d23cae13de3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-4b2f85d956a4fd192b98	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-1190000000-ab19bb69614d900386a0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-7290000000-6ceb7509f287b97356ab	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05fr-9000000000-a7ebfca0baaa5806c21a	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

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
Schouten, J. A., Bagga, S., Lloyd, A. J., de Pascale, G., Dowson, C. G., Roper, D. I., Bugg, T. D. (2006). "Fluorescent reagents for in vitro studies of lipid-linked steps of bacterial peptidoglycan biosynthesis: derivatives of UDPMurNAc-pentapeptide containing d-cysteine at position 4 or 5." Mol Biosyst 2:484-491. Pubmed: 17216029
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	61395
HMDB ID	Not Available
Pubchem Compound ID	25203551
Kegg ID	Not Available
ChemSpider ID	19260405
Wikipedia ID	Not Available
BioCyc ID	CPD0-2190
EcoCyc ID	CPD0-2190

Enzymes

Protein Details

1. L-Ala-D/L-Glu epimerase

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.

Protein Details

2. Protein mpaA

General function:: Involved in metallocarboxypeptidase activity
Specific function:: Specific function unknown
Gene Name:: mpaA
Uniprot ID:: P0ACV6
Molecular weight:: 26558

L-Ala-gamma-D-Glu (ECMDB20574) (M2MDB001377)

Structure for #<Compound:0x5cf75b0>

Enzymes

Reactions