(2S)-2-aminopentanedioic acid

• ChemBase ID: 28
• Molecular Formular: C5H9NO4
• Molecular Mass: 147.12926
• Monoisotopic Mass: 147.05315777
• SMILES: OC(=O)[C@@H](N)CCC(=O)O
• Canonical SMILES: OC(=O)CC[C@@H](C(=O)O)N
• InChI: InChI=1S/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/t3-/m0/s1
• InChIKey: WHUUTDBJXJRKMK-VKHMYHEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-aminopentanedioic acid
• IUPAC Traditional name: L-glutamic acid
• Brand Name: Aciglut; Glusate; Glutacid; Glutamicol; Glutamidex; Glutaminol; Glutaton
• Synonyms: L-2-Aminopentanedioic acid; Glu; L-GLUTAMIC ACID FREE ACID; L-Glutamic acid; (S)-2-Amino-1,5-pentanedioic Acid; Glusate; Glutacid; Glutamicol; Glutamidex; Glutaminol; Glutaton; L-α-Aminoglutaric Acid; α-Glutamic Acid; (2S)-2-Aminopentanedioic acid; (S)-(+)-Glutamic acid; (S)-2-Aminopentanedioic acid; (S)-Glutamic acid; 1-Aminopropane-1,3-dicarboxylic acid; 2-Aminoglutaric acid; 2-Aminopentanedioic acid; a-Glutamic acid; a-Aminoglutaric acid; L-(+)-Glutamic acid; L-a-Aminoglutaric acid; L-Glutamate; L-Glutaminic acid; Glutaminic acid; Glutamic acid; L-Glutamic Acid; L-(+)-Glutamic acid; Acidum glutamicum; L-2-Aminoglutaric acid; H-Glu-OH; (S)-2-AMinopentanedioic acid; 2-AMinopentanedioic acid; (S)-2-氨基戊二酸; L-谷氨酸; 谷氨酸

Database IDs

• CAS Number: 617-65-2; 56-86-0
• EC Number: 200-293-7
• MDL Number: MFCD00002634
• Beilstein Number: 1723801
• Merck Index: 144469
• PubChem SID: 24901609; 160963491; 24846358; 24895340; 46505816; 24895052; 24895223; 24872908
• PubChem CID: 33032
• FEMA ID: 3285
• E Number: E620

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.8777773
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -4.4458017
• LogD (pH = 7.4): -6.180975
• Log P: -3.241447
• Molar Refractivity: 31.2877 cm^3
• Polarizability: 12.69048 Å^3
• Polar Surface Area: 100.62 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -3.54
• LOG S: -0.26
• Solubility (Water): 8.06e+01 g/l

PROPERTIES

Physical Property

• Solubility: 1 M HCl: soluble1 M at 20 °C, clear, colorless; 1 M HCl: soluble100 mg/mL; 8.57 mg/mL at 25 oC [BULL,HB et al. (1978)]; Water
• Apperance: powder; White Solid
• Melting Point: 189-192°C dec.; 199-201°C; 205 °C (dec.)(lit.); 224-225°C
• Density: 1.525; 1.538 g/ml @ 20°C
• Optical Rotation: [α]20/D +31.5±1.0°, c = 5% in 5 M HCl; [α]20/D +31.5°, c = 2 in 5 M HCl; [α]20/D +32°, c = 10 in 2 M HCl; +31 (c=5 in 5N HCl)
• Absorption Wavelength: λ: 260 nm Amax: 0.1; λ: 280 nm Amax: 0.1
• Hydrophobicity(logP): -3.3

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• RTECS: LZ9700000
• German water hazard class: 1
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 20-25°C
• Regulation Compliance: FCC; FDA 21 CFR (172.320); FDA 21 CFR (182.1045)

Pharmacology Properties

• Gene Information: human ... CCR2(1231), GRIA1(2890), GRIA2(2891), GRIA4(2893), GRIK1(2897), GRIK2(2898), GRIK3(2899), GRIK5(2901), GRIN2B(2904), GRM2(2912), SLC1A1(6505), SLC1A2(6506)rat ... Gria1(50592), Grik1(29559), Grik2(54257), Grik4(24406), Grin2a(24409), Grm1(24414), Grm2(24415), Grm3(24416), Grm4(24417), Grm5(24418), Grm6(24419), Grm7(81672), Slc1a2(29482); human ... CCR2(1231), GRIA1(2890), GRIA2(2891), GRIA4(2893), GRIK2(2898), GRIK3(2899), GRIK5(2901), GRIN2B(2904), GRM2(2912), SLC1A1(6505), SLC1A2(6506)rat ... Gria1(50592), Grik1(29559), Grik2(54257), Grik4(24406), Grin2a(24409), Grm1(24414), Grm2(24415), Grm3(24416), Grm4(24417), Grm5(24418), Grm6(24419), Grm7(81672), Slc1a2(29482)

Product Information

• Purity: ≥98.5%; ≥99% (TLC); ≥99.0%; ≥99.0% (NT); ≥99.5% (NT); 97%; 98%; 98.5-100.5%; 99%; 99+%; 99-100%
• Grade: certified reference material; EP; JIS special grade; Kosher; NI; Ph Eur; PharmaGrade; ReagentPlus®; TraceCERT®
• Suitability: meets EP testing specifications; suitable for cell culture; suitable for manufacturing use
• Ignition Residue: ≤0.05% (as SO4); ≤0.1% (as SO4)
• Impurities: ≤0.5% foreign amino acids; endotoxin, tested; insoluble matter, passes filter test
• Cation Traces: Al: ≤5 mg/kg; Ba: ≤5 mg/kg; Bi: ≤5 mg/kg; Ca: ≤200 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤5 mg/kg; K: ≤50 mg/kg; Li: ≤5 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Mo: ≤5 mg/kg; Na: ≤200 mg/kg; NH4+: ≤100 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Sr: ≤5 mg/kg; Zn: ≤5 mg/kg
• Antion Traces: chloride (Cl-): ≤100 mg/kg; sulfate (SO42-): ≤150 mg/kg; sulfate (SO42-): ≤200 mg/kg
• Biological Source: from non-animal source
• Loss on Drying: ≤0.05% loss on drying, 20 °C (HV); ≤0.1% loss on drying, 110 °C
• Quality Level: GMP-COMPENDIA
• λ: 1 M in 1 M HCl
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Product Line: BioUltra
• Linear Formula: HO2CCH2CH2CH(NH2)CO2H

DETAILS

MP Biomedicals - 02101793

Free Acid
Purity: 99-100%
Crystalline

MP Biomedicals - 02194676

Free Acid
Cell Culture Reagent
Purity: 99-100%
Crystalline

DrugBank - DB00142

• Drug Groups: approved; nutraceutical
• Description: A peptide that is a homopolymer of glutamic acid. [PubChem]
• Indication: Considered to be nature's "Brain food" by improving mental capacities; helps speed the healing of ulcers; gives a "lift" from fatigue; helps control alcoholism, schizophrenia and the craving for sugar.
• Pharmacology: In addition to being one of the building blocks in protein synthesis, it is the most widespread neurotransmitter in brain function, as an excitatory neurotransmitter and as a precursor for the synthesis of GABA in GABAergic neurons.
• Toxicity: Glutamate causes neuronal damage and eventual cell death, particularly when NMDA receptors are activated, High dosages of glutamic acid may include symptoms such as headaches and neurological problems.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Absorbed from the lumen of the small intestine into the enterocytes.Absorption is efficient and occurs by an active transport mechanism.
• References: Smith QR: Transport of glutamate and other amino acids at the blood-brain barrier. J Nutr. 2000 Apr;130(4S Suppl):1016S-22S. [Pubmed] ; Okumoto S, Looger LL, Micheva KD, Reimer RJ, Smith SJ, Frommer WB: Detection of glutamate release from neurons by genetically encoded surface-displayed FRET nanosensors. Proc Natl Acad Sci U S A. 2005 Jun 14;102(24):8740-5. Epub 2005 Jun 6. [Pubmed] ; Reeds PJ, Burrin DG, Stoll B, Jahoor F: Intestinal glutamate metabolism. J Nutr. 2000 Apr;130(4S Suppl):978S-82S. [Pubmed] ; Corrie JE, DeSantis A, Katayama Y, Khodakhah K, Messenger JB, Ogden DC, Trentham DR: Postsynaptic activation at the squid giant synapse by photolytic release of L-glutamate from a 'caged' L-glutamate. J Physiol. 1993 Jun;465:1-8. [Pubmed] ; Augustin H, Grosjean Y, Chen K, Sheng Q, Featherstone DE: Nonvesicular release of glutamate by glial xCT transporters suppresses glutamate receptor clustering in vivo. J Neurosci. 2007 Jan 3;27(1):111-23. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - G5667

Biochem/physiol Actions
An excitatory amino acid neurotransmitter that is an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA).
Packaging
Manufactured and Packaged under cGMP

Sigma Aldrich - G1251

Biochem/physiol Actions
一种兴奋性氨基酸神经递质，为谷氨酸盐受体所有亚型(代谢型红藻氨酸、NMDA 和 AMPA)的激动剂。
包装
1 kg in poly bottle
100, 500 g in poly bottle
5 kg in poly drum
法律信息
ReagentPlus 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - G8415

Biochem/physiol Actions
Glutamic acid, or glutamate, the salt form of glutamic acid, functions as a neurotransmitter. Glutamic acid also plays a key role in many metabolic pathways. It is converted to α-ketoglutarate, a key component of the TCA cycle, and a precursor for the biosynthesis of nucleic acids and certain amino acids. In cells, glutamine is converted to glutamate by the enzyme glutaminase.
一种兴奋性氨基酸神经递质，为谷氨酸盐受体所有亚型(代谢型红藻氨酸、NMDA 和 AMPA)的激动剂。
包装
10 mg in autosmp vl

Sigma Aldrich - 49449

Biochem/physiol Actions
An excitatory amino acid neurotransmitter that is an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA).
Other Notes
Lesion-sparing agent, has excitotoxic properties1; May function as precipitating agent in protein crystallization2; Growth requirement of various microorganisms3

Sigma Aldrich - 128430

Biochem/physiol Actions
An excitatory amino acid neurotransmitter that is an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA).
Packaging
1 kg in poly bottle
100 g in poly bottle

Sigma Aldrich - W328502

Biochem/physiol Actions
An excitatory amino acid neurotransmitter that is an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA).
Packaging
1 kg in poly bottle
1 sample in glass bottle
5, 10, 25 kg in fiber drum

Sigma Aldrich - 95436

Analysis Note
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34. This CRM is traceable to NIST SRM.
Biochem/physiol Actions
An excitatory amino acid neurotransmitter that is an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA).
General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 09581

Biochem/physiol Actions
An excitatory amino acid neurotransmitter that is an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA).

Sigma Aldrich - 49450

Biochem/physiol Actions
An excitatory amino acid neurotransmitter that is an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA).

Sigma Aldrich - 12-0880

Biochem/physiol Actions
An excitatory amino acid neurotransmitter that is an agonist at all subtypes of glutamate receptors (metabotropic, kainate, NMDA, and AMPA).

Toronto Research Chemicals - G596960

A non-essential amino acid. Its salt form (glutamate) is an important neurotransmitter that plays a key role in long-term potentiation and is important for learning and memory. It is also a key molecule in cellular metabolism.

REFERENCES

• Smith QR: Transport of glutamate and other amino acids at the blood-brain barrier. J Nutr. 2000 Apr;130(4S Suppl):1016S-22S. Pubmed
• Okumoto S, Looger LL, Micheva KD, Reimer RJ, Smith SJ, Frommer WB: Detection of glutamate release from neurons by genetically encoded surface-displayed FRET nanosensors. Proc Natl Acad Sci U S A. 2005 Jun 14;102(24):8740-5. Epub 2005 Jun 6. Pubmed
• Reeds PJ, Burrin DG, Stoll B, Jahoor F: Intestinal glutamate metabolism. J Nutr. 2000 Apr;130(4S Suppl):978S-82S. Pubmed
• Corrie JE, DeSantis A, Katayama Y, Khodakhah K, Messenger JB, Ogden DC, Trentham DR: Postsynaptic activation at the squid giant synapse by photolytic release of L-glutamate from a 'caged' L-glutamate. J Physiol. 1993 Jun;465:1-8. Pubmed
• Augustin H, Grosjean Y, Chen K, Sheng Q, Featherstone DE: Nonvesicular release of glutamate by glial xCT transporters suppresses glutamate receptor clustering in vivo. J Neurosci. 2007 Jan 3;27(1):111-23. Pubmed
• McEntee, W., et al.: Psychopharmacology, 111, 391 (1993)
• Manev, H., et al.: Mol. Pharmacol., 36, 106 (1993)
• For use as a chiral building-block in the synthesis of the (S)-isomer of -butyrolactone-4-carboxylic acid, see: Org. Synth. Coll., 7, 99 (1990):
  
• For the differential protection of the ɑ-carboxyl group of N-protected glutamic acid by reaction with formaldehyde to form the cyclic 5-oxazolidinone, see: Synthesis, 542 (1989).