(2S)-2-aminopentanedioic acid

• ChemBase编号: 28
• 分子式: C5H9NO4
• 平均质量: 147.12926
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: (2S)-2-aminopentanedioic acid
• IUPAC传统名: L-glutamic acid
• 商标名: Aciglut; Glusate; Glutacid; Glutamicol; Glutamidex; Glutaminol; Glutaton
• 别名: (S)-2-氨基戊二酸; L-谷氨酸; 谷氨酸; 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

登记号

• CAS号: 56-86-0; 617-65-2
• EC号: 200-293-7
• MDL号: MFCD00002634
• Beilstein号: 1723801
• 默克索引号: 144469
• PubChem SID: 24901609; 160963491; 24846358; 24895340; 46505816; 24895052; 24895223; 24872908
• PubChem CID: 33032
• FEMA编号: 3285
• E编码: E620

理论计算性质

JChem

• Acid pKa: 1.8777773
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): -4.4458017
• LogD (pH = 7.4): -6.180975
• Log P: -3.241447
• 摩尔折射率: 31.2877 cm^3
• 极化性: 12.69048 Å^3
• 极化表面积: 100.62 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -3.54
• LOG S: -0.26
• 溶解度: 8.06e+01 g/l

分子性质

理化性质

• 溶解度: 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
• 外观: powder; White Solid
• 熔点: 189-192°C dec.; 199-201°C; 205 °C (dec.)(lit.); 224-225°C
• 密度: 1.525; 1.538 g/ml @ 20°C
• 比旋光度: [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)
• 紫外吸收波长: λ: 260 nm Amax: 0.1; λ: 280 nm Amax: 0.1
• 疏水性(logP): -3.3

安全信息

• 保存条件: Refrigerator; Room Temperature (15-30°C)
• RTECS编号: LZ9700000
• 德国WGK号: 1
• TSCA收录: 是
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 20-25°C
• Regulation Compliance: FCC; FDA 21 CFR (172.320); FDA 21 CFR (182.1045)

药理学性质

• 相关基因信息: 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)

产品相关信息

• 纯度: ≥98.5%; ≥99% (TLC); ≥99.0%; ≥99.0% (NT); ≥99.5% (NT); 97%; 98%; 98.5-100.5%; 99%; 99+%; 99-100%
• 级别: certified reference material; EP; JIS special grade; Kosher; NI; Ph Eur; PharmaGrade; ReagentPlus®; TraceCERT®
• 适用性: meets EP testing specifications; suitable for cell culture; suitable for manufacturing use
• 燃烧残渣: ≤0.05% (as SO4); ≤0.1% (as SO4)
• 杂质: ≤0.5% foreign amino acids; endotoxin, tested; insoluble matter, passes filter test
• 痕量阳离子: 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
• 痕量阴离子: chloride (Cl-): ≤100 mg/kg; sulfate (SO42-): ≤150 mg/kg; sulfate (SO42-): ≤200 mg/kg
• 生物来源: from non-animal source
• 干燥失重: ≤0.05% loss on drying, 20 °C (HV); ≤0.1% loss on drying, 110 °C
• 产品质量级别: GMP-COMPENDIA
• λ: 1 M in 1 M HCl
• 药典: testing & handling conforms to Pharmacopeia
• 产品线: BioUltra
• 线性分子式: HO2CCH2CH2CH(NH2)CO2H

详细说明

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
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
根据 cGMP 制造和包装

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
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。
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
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 g in poly bottle

Sigma Aldrich - W328502

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
1 sample in glass bottle
5, 10, 25 kg in fiber drum

Sigma Aldrich - 95436

Analysis Note
该有证标准物质 (CRM) 根据 ISO/IEC 17025 和 ISO 指南 34 生产和认证。该有证标准物质可溯源到 NIST 标准参考物质。
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。
General description
证书上给出了含不确定度的认证含量（定量 NMR 法测定）和有效期。 证书下载：http://www.sigma-aldrich.com。
法律信息
TraceCERT 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 09581

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。

Sigma Aldrich - 49450

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。

Sigma Aldrich - 12-0880

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。

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.

参考文献

• 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).