D-Glutamic acid
D-Glutamic Acid
CAS: 6893-26-1;138-16-9
Molecular Formula: C5H9NO4
D-Glutamic acid - Names and Identifiers
| Name | D-Glutamic Acid |
| Synonyms | NSC 77686 H-D-Glu-OH D-Glutamic Acid D-Glutaminic acid D(-)-Glutamic acid (2R)-GlutaMic Acid D-(-)-Glutamic acid D-α-AMinoglutaric acid D-2-Aminoglutaric acid (2R)-2-Aminoglutaric acid (2R)-2-ammoniopentanedioate D-1-AMinopropane-1,3-dicarboxylic acid |
| CAS | 6893-26-1 138-16-9 |
| EINECS | 230-000-8 |
| InChI | InChI=1/C5H9NO4/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H,7,8)(H,9,10)/p-1/t3-/m1/s1 |
| InChIKey | WHUUTDBJXJRKMK-GSVOUGTGSA-N |
D-Glutamic acid - Physico-chemical Properties
| Molecular Formula | C5H9NO4 |
| Molar Mass | 147.13 |
| Density | 1.5380 |
| Melting Point | 200-202°C (subl.)(lit.) |
| Boling Point | 267.21°C (rough estimate) |
| Specific Rotation(α) | -31.3 º (c=10, 2 N HCl) |
| Flash Point | 155.7°C |
| Water Solubility | 7 g/L (20 ºC) |
| Solubility | Water (Slightly) |
| Vapor Presure | 2.55E-05mmHg at 25°C |
| Appearance | White crystal |
| Color | White to off-white |
| Merck | 14,4469 |
| BRN | 1723800 |
| pKa | pK1:2.162(＋1);pK2:4.272(0);pK3:9.358(－1) (25°C) |
| Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
| Refractive Index | 1.4210 (estimate) |
| MDL | MFCD00063112 |
| Physical and Chemical Properties | White Crystal or crystalline powder; Soluble in water, slightly soluble in ethanol, insoluble in ether; Specific optical rotation [α]20D-30.5 °(0.5-2 mg/mL, 6mol/L HCl),LD50 (human, intravenous) 117 mg/kg. |
| Use | Amino acid drugs. |
| In vitro study | Various d-amino acids, such as D-serine, D-aspartic acid (D-Asp), and D-glutamic acid (D-Glu) are widely found in mammals including human beings and they are now thought to be the candidates of novel physiologically active substances and/or biomarkers. D-[Asp/Glu] (4 mg/mL) inhibits IgE binding (75%) to peanuts while D-Glu, D-Asp has no inhibitory effect. IgE is specific for D-[Asp/Glu] and may have the potential for removing IgE or reducing IgE binding to peanut allergens. |
| In vivo study | D-glutamic acid is currently paid attention as a modulator of neuronal transmission and hormonal secretion. It is metabolized only by D-aspartate oxidase in mammals. After intraperitoneal injection, L-glutamate is catabolized via a-ketoglutarate, whereas D-glutamate is converted to n-pyrrolidone carboxylic acid. Carbon 2 of both D- and L-glutamate is converted in the cecum to the methyl carbon of acetate. Both rat liver and kidney catalyze the conversion of D-glutamic acid to n-pyrrolidone carboxylic acid. |
D-Glutamic acid - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S24/25 - Avoid contact with skin and eyes. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| FLUKA BRAND F CODES | 10 |
| TSCA | Yes |
| HS Code | 29224200 |
D-Glutamic acid - Reference
| Reference Show more | 1. [IF=7.79] Ye Lu et al."Enhancing hydrogel-based long-lasting chemiluminescence by a platinum-metal organic framework and its application in array detection of pesticides and D-amino acids."Nanoscale. 2020 Feb;12(8):4959-4967 |
D-Glutamic acid - Study on the relationship between D-glutamic acid and the pathogenesis of Parkinson's model rats
from VIP Journal Professional Edition
Author:
Liu Chengwei , Lujie , Lu Xin , P. P. , Cai Yunling
Abstract:
objective: to observe the changes of D-glutamic acid in the midbrain of Parkinson's model rats, and to explore the damage effect of D-enantiomer of excitatory neurotransmitter on glutamatergic neurons and its correlation with the development of Parkinson's disease. Methods: adult C57BL male mice were randomly divided into control group and model group. In the model Group, 1-methyl-4-phenyl-1.2.3.6-tetrahydropyridine (MPTP) was intraperitoneally injected to prepare Parkinson's disease model mice. The content of D-glutamic acid in midbrain was detected by pre-column derivatization high performance liquid chromatography, and the changes of glutamatergic neurons in substantia nigra and caudate putamen were observed by immunohistochemical ABC method. Results: compared with the control group, the content of d-glutamic acid in the midbrain tissue of the model group was significantly increased after 1 D of MPTP injection, and gradually decreased after 3 d; The number of glutamatergic neurons was significantly decreased after 3 d. Conclusion: D-glutamate may have the same excitotoxicity as L-form enantiomer in mesencephalon, and may be involved in the pathogenesis of Parkinson's disease.
expand
Key words:
Parkinson's disease D-glutamic acid high performance liquid chromatography mouse
DOI:
10.3969/j.issn.1001-1633.2007.02.004
cited:
year:
2007
Last Update：2024-01-02 23:10:35
D-Glutamic acid - A new method for the preparation of D-glutamic acid from L-glutamic acid
from VIP Journal Professional Edition
Author:
Jiang Lijian , zhuyang , Wang Yuting
Abstract:
D-glutamic acid was prepared from L-glutamic acid by esterification, racemization, chemical resolution and hydrolysis. L-2, 3-dibenzoyltartaric acid (L-DBTA) is reacted with DL-glutamic acid-& gamma;-ethyl ester in aqueous solution at 65-70 °c to form a diastereomeric salt, cooled to 0-5 °c, D-glutamic acid · L-DBTA salt was precipitated, filtered and hydrolyzed to obtain D-glutamic acid. The yield was 85% and the optical purity was over 99%.Key words:
DOI:
10.3969/j.issn.1671-3206.2006.04.023
cited:
year:
2006
Last Update：2024-01-02 23:10:35
D-Glutamic acid - Method for preparing D-glutamic acid
from Baidu Library
Application (patent) number:
CN201310549837.7
applicant (patent):
Yixing Qiancheng biology Co., Ltd.
inventor:
Abstract:
The invention discloses a method for preparing D-glutamic acid, which is prepared by esterification, racemization, resolution, hydrolysis and ion exchange using L-glutamic acid as raw material, comprises the following steps:(1)L-glutamic acid and methanol are reacted with hydrogen chloride as catalyst for 2-5H to obtain L-glutamic acid-& gamma;-methyl ester;(2)L-glutamic acid-& gamma;-methyl ester dissolved in butyric acid, add resolving agent D-tartaric acid, racemic catalyst salicylaldehyde, heated to 80~90 ℃, after 6-10 hours of reaction, D-glutamic acid ester-D-tartrate is obtained;(3)D-glutamic acid ester-D-tartrate is hydrolyzed by heating in an acidic aqueous solution, the hydrolysis solution was separated by cation exchange resin column, and finally D-glutamic acid was obtained. In the method for preparing D-glutamic acid of the present invention, the actual yield of D-glutamic acid can reach more than 80%, and the chiral purity can reach more than 99.5%; D-tartaric acid is used as a resolving agent, which is easy to obtain and can be reused, the cost has been greatly reduced.
Last Update：2024-01-02 23:10:35
D-Glutamic acid - Study on the effect of D-glutamic acid on the biofilm of Porphyromonas gingivalis
from hownet
Author:
Abstract:
Background: biofilm is an ecological environment formed on the surface of a certain medium by the extracellular matrix secreted by the microbial community. Clinically, more than 80% of bacterial infections, especially chronic diseases, are associated with biofilms. Dental plaque is a typical biofilm structure, which can accommodate the survival of a variety of bacteria in the oral ecological system. Bacteria in biofilms are different from planktonic bacteria in that they have strong resistance to antimicrobial agents and host defense mechanisms, and their metabolic activity and gene expression are also different. Peri-implant inflammation and peri-implant mucositis are closely related to the accumulation of dental plaque biofilm in the oral cavity. Dental plaque biofilm will destroy the host-microbial homeostasis balance at the interface between the implant and the mucosa, causing inflammatory lesions. Porphyromonas gingivalis plays a very important role in the occurrence and development of Peri-implant diseases. Therefore, to prevent or control the occurrence and development of Peri-implant inflammation, the key is to effectively destroy or prevent the implant surface formation of Porphyromonas gingivalis biofilm, however, the current commonly used clinical treatment of peri-implantitis methods can not guarantee the effective removal of biofilm on the implant surface without damaging the implant surface or surrounding tissues. The inhibitory effect of D-amino acid on the formation of biofilm and the dispersing effect on the formed biofilm have been confirmed. It can inhibit the growth of biofilm matrix and the expression of related genes and proteins, or during the synthesis of peptidoglycan, some exogenous D-amino acids are integrated into the peptide side chain of peptidoglycan to affect the strength of peptidoglycan and the flexibility of peptidoglycan, thus inhibiting the formation of bacterial biofilm. Studies have shown that different D-amino acids have different effects on biofilm of different strains. At present, the effect of D-amino acid on biofilm is mainly focused on Pseudomonas aeruginosa, Bacillus subtilis and Staphylococcus aureus biofilm. Porphyromonas gingivalis is a common bacterium in the oral cavity, which plays an important role in the occurrence and development of periodontal diseases and peri-implant diseases, however, there are few studies on the use of D-Amino Acids against P. Gingivalis biofilm. As an important component of cell wall peptidoglycan, whether D-glutamic acid has the effect of anti-Porphyromonas gingivalis biofilm has not been reported. Therefore, this experiment will explore the effect of different concentration gradients of D-glutamic acid on the biofilm of P. Gingivalis, in order to provide theoretical support for the clinical treatment of D-glutamic acid in the future. Methods: The concentration of preparation were 0.05 mM,0.5 mM,5 mM,10 mM,25 mM,35 mM,45 mM D-glutamic acid solution and to detect its effect on Porphyromonas gingivalis ATCC 33277 planktonic bacteria and biofilm. The cultured suspension of Porphyromonas gingivalis was inoculated in 24-well/96-well plates and incubated for 72 h, the effect of D-glutamic acid on Porphyromonas gingivalis biofilm was observed by scanning electron microscopy and live bacterial staining. Results: 1,0.05 mM,0.5 mM,5 mM,10 mM,25 mM,35 mM D-glutamic acid had no significant effect on the growth curve of P. Gingivalis. The concentration of 45mm D-glutamic acid decreased the number of planktonic bacteria and prolonged the lag phase. 2, when D-glutamic acid is used to prevent the formation of P. Gingivalis biofilm, 5 mM,10 mM,25 mM,35 mM, D-glutamate at a concentration of 45 mM led to a decrease in the biofilm biomass of P. Gingivalis, 10 mM,25 mM,35 mM, D-glutamate at a concentration of 45 mM decreased the metabolic capacity of P. Gingivalis biofilm, 0.05 mM,0.5 mM,5 mM,10 mM,25 mM,35 mM, the production of exopolysaccharides was reduced by 45 mM D-glutamate. When the concentration of 5 mM,10 mM,25 mM,35 mM,45 mM D-glutamic acid was added, the number of biofilm bacteria decreased, the proportion of living bacteria decreased, and the proportion of dead bacteria increased. 3, when used to destroy the biofilm of P. Gingivalis, 0.5 mM,5 mM,10 mM,25 mM,35 mM, D-glutamic acid at a concentration of 45 mM led to a decrease in the biomass of P. Gingivalis biofilm, and D-glutamic acid at a concentration of 35 mM,45 mM led to a decrease in the metabolic capacity of P. Gingivalis biofilm, 0.05 mM,0.5 mM,5 mM,10 mM,25 mM,35 mM,45 mM D-glutamic acid reduced the production of extracellular polysaccharide. After adding D-glutamic acid at concentrations of 5 mM,10 mM,25 mM,35 mM,45 mM, the number of biofilm bacteria decreased, and the individual bacteria became long rod-like, at this time, the proportion of living dead bacteria did not change significantly. Conclusion: 1,0.05 mM-35 mM D-glutamic acid has no significant effect on the growth of Porphyromonas gingivalis. D-glutamic acid at a concentration of 45 mM inhibited the growth of planktonic bacteria of Porphyromonas gingivalis. 2,D-glutamic acid concentration of 10 mM or more can effectively inhibit the formation of biofilm, the biofilm biomass of Porphyromonas gingivalis, the activity of bacteria in the biofilm and the production of extracellular polysaccharide are reduced. 3, used to destroy the mature biofilm of Porphyromonas gingivalis, D-glutamic acid concentration is greater than or equal to 35 mM can destroy the formed biofilm, at this time, the biofilm biomass of Porphyromonas gingivalis, the activity of bacteria in the biofilm and the production of extracellular polysaccharide were reduced.
degree level:
MSc
degree year:
2019
Last Update：2024-01-02 23:10:35
D-Glutamic acid - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| biological activity | D-glutamic acid is the enantiomer of L-glutamic acid and is widely used in drugs and foods. |
| Use | for biochemical studies. amino acid drugs. |
| production method | with acetyl-DL-glutamic acid as raw material, after acylase treatment, L-form was removed, refined, the product was dried. |
Last Update：2024-04-10 22:40:09
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View History
D-Glutamic acid
吡唑-1-甲脒单盐酸盐
2-(2,5-二甲基苯磺酰胺基)-4-(甲基硫烷基)丁酸
4,5-二甲氧基-2-硝基苯甲酸乙酯
异噻唑啉酮 标准品
Poly(Vinyl Acetate-CO-Butyl Maleate-CO-Isobornyl Acrylate)
tetrabutylazanium:fluoride:hydrate
补骨脂色烯查耳酮
5-Chloro-2-formylphenylboronic acid
2-苯基苯丁酮
吡唑-1-甲脒单盐酸盐
2-(2,5-二甲基苯磺酰胺基)-4-(甲基硫烷基)丁酸
4,5-二甲氧基-2-硝基苯甲酸乙酯
异噻唑啉酮 标准品
Poly(Vinyl Acetate-CO-Butyl Maleate-CO-Isobornyl Acrylate)
tetrabutylazanium:fluoride:hydrate
补骨脂色烯查耳酮
5-Chloro-2-formylphenylboronic acid
2-苯基苯丁酮