Gamma-Glutamylalanine
Basic information
- CAS
5875-41-2- Standard SMILES
C[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)O- InChIKey
WQXXXVRAFAKQJM-WHFBIAKZSA-N- Molecular formula
- C8H14N2O5
- Average molar mass
- 218.21 g/mol
- Monoisotopic mass
- 218.09027155
Overview
Gamma-Glu-Ala is a gamma-glutamylalanine obtained by formal condensation of the gamma-carboxy group of L-glutamic acid with the amino group of L-alanine. It has a role as a Saccharomyces cerevisiae metabolite and a plant metabolite. It is a conjugate acid of a gamma-Glu-Ala(1-).
Names & identifiers
- Preferred name
- Gamma-Glutamylalanine
- IUPAC
- (2S)-2-amino-5-[[(1S)-1-carboxyethyl]amino]-5-oxopentanoic acid
- English name
- H-gamma-Glu-Ala-OH
- Molecular formula
- C8H14N2O5
- Molecular weight
- 218.21
Names & synonyms
5875-41-2gamma-Glutamylalaninegamma-Gln-ala(2S)-2-Amino-5-[[(1S)-1-carboxyethyl]amino]-5-oxopentanoic acidCHEBI:50621(2S)-2-amino-5-(((1S)-1-carboxyethyl)amino)-5-oxopentanoic acidRefChem:922048H-GAMMA-GLU-ALA-OHgamma-L-Glutamyl-L-alaninegamma-Glu-Ala5-L-Glutamyl-L-alanineH-Glu(Ala-OH)-OH
Show more names
γ-Glu-Alag-Glu-Ala.γ-Glu-Ala-OHH-GLU(ALA)-OHH-g-Glu-Ala-OHH-γ-Glu-Ala-OH
g-Glu-AlaL-gamma-glutamyl-L-alanineMFCD00037215(2S)-2-amino-4-{[(1S)-1-carboxyethyl]carbamoyl}butanoic acidH-?-Glu-Ala-OH(S)-2-Amino-5-(((S)-1-carboxyethyl)amino)-5-oxopentanoic acidH-|A-Glu-Ala-OHg-Glu-Ala-OH
Database identifiers
- CAS
5875-41-2- PubChem CID
- 440103
- DTXSID
DTXSID80974270
Properties
Computed structural properties
- XLogP
- -3.8
- Topological polar surface area
- 130 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 6
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 266
Experimental & physicochemical properties
Physical DescriptionSolid
Collision Cross Section140.25 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
Physicochemical properties
- Melting point
- 188 · 188-192 °C (lit.)
- Boiling point
- 564.4 · 564.4±50.0 °C(Predicted)
- Density
- 1.362 · 1.362±0.06 g/cm3(Predicted)
- storage temp.
- -15 °C · -15°C
- solubility
- 50 · Water:50.0(Max Conc. mg/mL);229.14(Max Conc. mM)
- pka
- 2.22 · 2.22±0.10(Predicted)
- form
- Solid
- color
- White to off-white
- optical activity
- 20 · [α]20/D 26.5°, c = 5 in H2O
- Major Application
- peptide synthesis
- InChI
- 1S/C8H14N2O5/c1-4(7(12)13)10-6(11)3-2-5(9)8(14)15/h4-5H,2-3,9H2,1H3,(H,10,11)(H,12,13)(H,14,15)/t4-,5-/m0/s1
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
Tissue LocationsPlacenta
Cellular LocationsExtracellular
Metabolite Pathways5-oxoprolinase deficiency
Applications
UsesH-GAMMA-GLU-ALA-OH is a proteolytic breakdown product of larger proteins that is suitable for peptide synthesis. It is also used in a biological study that looked at kokumi substances and bacteria in fermented Thai freshwater fish.
Additional notes
DefinitionChEBI: A gamma-glutamylalanine obtained by formal condensation of the gamma-carboxy group of L-glutamic acid with the amino group of L-alanine.
Related reactions
0 records
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Compound notes
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