5959-95-5
D(-)-Glutamine
CAS: 5959-95-5
Molecular Formula: C5 H10 N2 O3
5959-95-5 - Names and Identifiers
| Name | D(-)-Glutamine |
| Synonyms | H-D-Gln-OH D-Glutamine D-GLUTAMINE D(-)-GLUTAMINE D(-)-Glutamine D-GLUTAMINE extrapure D-GLUTAMIC ACID 5-AMIDE D-GLUTAMINIC ACID 5-AMIDE D(-)-GLUTAMIC ACID-5-AMIDE D(-)-Glutamic acid-5-amide Citric Acid, Monohydrate, Crystal, Reagent D-2-Aminoglutaramic acid, D-Glutamic acid 5-amide |
| CAS | 5959-95-5 |
| EINECS | 673-968-0 |
| InChI | InChI=1/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m1/s1 |
| InChIKey | ZDXPYRJPNDTMRX-GSVOUGTGSA-N |
5959-95-5 - Physico-chemical Properties
| Molecular Formula | C5 H10 N2 O3 |
| Molar Mass | 146.14 |
| Density | 1.3394 (rough estimate) |
| Melting Point | 184-185 °C |
| Boling Point | 265.74°C (rough estimate) |
| Specific Rotation(α) | -32 º (589nm, c=10, N HCl) |
| Water Solubility | 42.53g/L(temperature not stated) |
| Solubility | Soluble in water (9 mg/ml at 25 °C), DMSO (<1 mg/ml at 25 °C), and ethanol (<1 mg/m |
| Appearance | White crystalline powder |
| Color | White |
| BRN | 1723796 |
| pKa | 2.27±0.10(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
| Refractive Index | -33 ° (C=5, 5mol/L H |
| MDL | MFCD00065607 |
| Physical and Chemical Properties | Melting Point: 185 |
| In vitro study | Glutamine is a key amino acid in the central nervous system (CNS), playing an important role in the glutamate/GABA-Glutamine cycle (GGC). In the GGC,Glutamine is transferred from astrocytes to neurons, where it will replenish the inhibitory and excitatory neurotransmitter pools. D-Glutamine has been used to study its role in conferring protection against acetaldehyde-induced disruption of barrier function in Caco-2 cell monolayer. Role of L-Glutamine in the protection of intestinal epithelium from acetaldehyde-induced disruption of barrier function is evaluated in Caco-2 cell monolayer. L-Glutamine reduced the acetaldehyde-induced decrease in transepithelilal electrical resistance and increase in permeability to inulin and lipopolysaccharide in a time- and dose-dependent manner; D-Glutamine, L-aspargine, L-arginine, L-lysine, or L-alanine produced no significant protection. D-Glutamine also fails to influence the acetaldehyde-induced decrease in TER and increase in inulin flux. D-Glutamine or glutaminase inhibitor by themselves did not influence TER or inulin flux in control or acetaldehyde-treated cell monolayers. Lack of effect of D-Glutamine in protection from acetaldehyde indicates that the L-Glutamine-mediated protection is stereospecific. |
5959-95-5 - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S27 - Take off immediately all contaminated clothing. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| HS Code | 29241900 |
5959-95-5 - Study on preparation of D-glutamine by biotransformation
from VIP Journal Professional Edition
Author:
qianshaosong , Wu Xiaoyan , Liu Yi , Chen ran , Li Jiayou , jiao Qingcai
Abstract:
A new method for the preparation of D-glutamine is reported, which uses L-glutamine decarboxylase of E. Coli AS1.505 to stereoselectively convert D, the L-form enantiomer in L-glutamine was degraded into 4-amino-butanamide, and D-glutamine was isolated. At the same time, the effects of temperature, pH and other factors on the activity of L-glutamine decarboxylase were investigated. The experimental results show that the optimum conditions are: temperature 37 ℃, transformation system pH = 4.8, cell mass concentration 5g/L, tween-80 mass concentration 0.15g/L, cell age 14 h, L-glutamine decarboxylase with substrate concentration of 40g/L.L-glutamine decarboxylase can achieve 4200U specific enzyme activity under the optimum conversion conditions, the yield of D-glutamine reached 92% of the theoretical yield.
Key words:
L-glutamine decarboxylase enzymatic conversion D-glutamine
DOI:
10.3321/j.issn:0253-4320.2005.09.012
cited:
year:
2005
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Last Update：2024-01-02 23:10:35
5959-95-5 - Establishment and validation of high performance liquid chromatographic method for determination of glycyl-D-glutamine
from VIP Journal Professional Edition
Author:
Yang Wanyun, xiao Hairong, Sun Guolin, Pan Xiao
Abstract:
objective: to detect glycyl-D-glutamine by high performance liquid chromatography and verify the method. Methods: glycyl-L-glutamine and glycyl-D-glutamine were derivatized and separated by HPLC, system suitability, linearity, sensitivity, precision, accuracy, solution stability and durability. Results: the linear correlation coefficient was 0.999 1 and the linear range was 0.450~6.750 μg/mL. The limit of detection was 101 ng/mL and the limit of quantitation was 435 ng/mL; the relative standard deviation of repeatability was 1.85%, the relative standard deviation of intermediate precision was 2.51%, the average recovery was 94.9%, and the relative standard deviation was 3.14%; the stability of the test solution and the control solution was at least 19 hours; The column temperature and the mobile phase flow rate were fine-tuned, and the durability was good. Conclusion: HPLC can be used for the determination of glycyl-D-glutamine, and the method is simple and convenient.
Key words:
HPLC, glycyl-D-glutamine, methodology validation
year:
2020
Last Update：2024-01-02 23:10:35
5959-95-5 - Method for preparing D-glutamine by chemical enzymatic method
from Palm Bridge research
Application (patent) number:
CN201911112311.6
application date:
2019-11-14
Public/Announcement Number:
CN110643670A
Public/announcement date:
2020.01.03
applicant (patent):
Hubei Xinyuan Biological Engineering Co., Ltd.
inventor:
Chen Cheng , Wu Cong , Cheng Wenying , Gan Fei , Du Qinglin , Liu Junzhong , jiao Qingcai
National and provincial code:
CN421022
Abstract:
The present invention provides a method for preparing D-glutamine by chemo-enzymatic method. The method is carried out according to the following steps: 1. Preparing N-phthaloyl DL glutamic acid; 2. Preparing N-phthaloyl DL glutamic anhydride; 3. Preparing N-phthaloyl DL glutamine; 4, preparation of DL glutamine; 5, culture preparation of aminopeptidase; 6, aminopeptidase split DL glutamine. In the invention, DL glutamine is prepared by using DL glutamic acid with low cost as raw material through four steps of simple chemical reaction, and the process parameters are optimized, the yield of DL glutamine is increased from 57% to 67%; L-glutamic acid and D-glutamine were obtained by separation of DL-glutamine with aminopeptidase. The yield of D-glutamine reached 95% of the theoretical value. The invention has the advantages of low raw material cost, simple process route, environmental protection, and is conducive to industrial implementation.
Last Update：2024-01-02 23:10:35
5959-95-5 - Preparation of D-glutamine
from VIP Journal Professional Edition
Abstract:
Preparation of optically pure D-glutamine by chemical synthesis and biotransformation is reported. DL-glutamine was first chemically synthesized on a pilot scale. That is, with cheap DL-glutamic acid as raw material, using phthaloyl as protective group to protect the α-amino group of L-glutamic acid, acetic anhydride refluxed for 15min, its intramolecular dehydration to produce N-phthaloyl-DL-glutamic anhydride, at room temperature, the intermediate N-phthaloyl-DL-glutamine was formed by the reaction with 2mol/L ammonia solution, and the protective group was removed by the reaction of the intermediate product with 0.5mol/L hydrazine hydrate for 48h at room temperature, DL-glutamine was obtained in 57% overall yield. E. Coli (E.coli.AS1.505) the L-form enantiomer of DL-glutamine at a substrate concentration of 30g/L was completely converted into 4-aminobutyramide within 8h by decarboxylase, and D-glutamine was isolated.Key words:
D-glutamine; DL-glutamic acid; decarboxylase
DOI:
CNKI:SUN:YJHU.0.2006-04-016
year:
2006
Last Update：2024-01-02 23:10:35
5959-95-5 - Introduction
The unnatural isomer of glutamine is actually insoluble in methanol, ethanol, ether and benzene.
Last Update：2022-10-16 17:26:48
5959-95-5 - Use
is a medicinal amino acid, used in the treatment of gastric and duodenal ulcers and mental retardation in young children and other diseases, but also the treatment of leukemia drug intermediates.
Last Update：2024-04-09 15:16:15
5959-95-5 - Reference Information
| biological activity | D-Glutamine is the D-stereoisomer of cell-permeable Glutamine. |
| Use | is a medicinal amino acid used to treat gastric and duodenal ulcers and mental retardation in young children, it is also an intermediate of drugs for the treatment of leukemia. |
Last Update：2024-04-09 20:45:29
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Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052
Wechat: 15671228036
Spot supply
Product Name: D-Glutamine Visit Supplier Webpage Request for quotationCAS: 5959-95-5
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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