DL-Glutamic acid
(Synonyms: DL-谷氨酸) 目录号 : GC61703DL-谷氨酸是作为基本代谢产物的谷氨酸的共轭酸。与多晶型物α和βL-谷氨酸的第二相相比,DL-谷氨酸具有更好的稳定性。
Cas No.:617-65-2
Sample solution is provided at 25 µL, 10mM.
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DL-Glutamic acid is the conjugate acid of Glutamic acid, which acts as a fundamental metabolite. Comparing with the second phase of polymorphs α and β L-Glutamic acid, DL-Glutamic acid presents better stability[1].
[1]. F M S Victor, et al. Pressure-induced phase transitions in DL-glutamic acid monohydrate crystal. Spectrochim Acta A Mol Biomol Spectrosc. 2020 Apr 5;230:118059.
Cas No. | 617-65-2 | SDF | |
别名 | DL-谷氨酸 | ||
Canonical SMILES | NC(CCC(O)=O)C(O)=O | ||
分子式 | C5H9NO4 | 分子量 | 147.13 |
溶解度 | 储存条件 | Store at -20°C | |
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1 mg | 5 mg | 10 mg | |
1 mM | 6.7967 mL | 33.9836 mL | 67.9671 mL |
5 mM | 1.3593 mL | 6.7967 mL | 13.5934 mL |
10 mM | 0.6797 mL | 3.3984 mL | 6.7967 mL |
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Pressure-induced phase transitions in DL-Glutamic acid monohydrate crystal
Spectrochim Acta A Mol Biomol Spectrosc 2020 Apr 5;230:118059.PMID:32000059DOI:10.1016/j.saa.2020.118059.
DL-Glutamic acid monohydrate crystal was synthesized from an aqueous solution by slow evaporation technique. The crystal was submitted to high-pressure (1 atm-14.3 GPa) to investigate its vibrational behavior and the occurrence of phase transitions. We performed Raman spectroscopy as probe and through the analysis of the spectra we discovered three structural phase transitions. The first one occurs around 0.9 GPa. In this phase transition, glutamic acid molecules suffer modifications in their conformations while water molecules are less affected. The second phase transition at 4.8 GPa involves conformational changes related to CO2-, NH3+ units and the water molecules, while the third one, between 10.9 and 12.4 GPa, involves motions of several parts of the glutamic acid as well as the water molecules. Considering the dynamic of high pressure, the second phase of DL-Glutamic acid monohydrate crystal presented a better stability compared with the second phase of its polymorphs α and β L-glutamic acid. In addition, water molecules seem to play important role on this structural stability. All changes are reversible.
Effects of D-, DL-and L-glutamic acid on chicks
J Nutr 1975 Aug;105(8):1012-9.PMID:1142007DOI:10.1093/jn/105.8.1012.
Studies were conducted to investigate the effects of D-, DL-, or L-glutamic acid on the chick. Supplementation of levels of L-glutamic acid to an amino acid mixture containing adequate levels of all the indispensable amino acids plus cystine and tyrosine resulted in increased growth up to 10% L-glutamic acid in the diet. Chicks tolerated as much as 15% L-glutamic acid with no growth retardation. Supplementation of D-glutamic acid at levels of 3.75 or 5% resulted in growth depressions of 18 and 38%, respectively, at the end of a 2-week experiment. Significant growth-depressing effects of these levels of D-glutamic acid and 7.5% of DL-Glutamic acid were also observed with an amino acid diet as well as an isolated soybean protein diet. The growth-depressing effect was most severe during week 2 of the experiment. Additional vitamins and amino acid supplements failed to reverse the growth-depressing effect. Plasma glutamic acid concentration was not altered by the inclusion of D-glutamic acid in the diet, but generally, plasma free amino acid concentrations were increased. This was especially true of arginine. Free glutamic acid increased in the kidney and was lowered in the liver. Free ammonia was increased in both the liver and kidney when the D form was included in the diet. Implications of these findings are discussed.
Streptomyces roseoverticillatus produces two different poly(amino acid)s: lariat-shaped gamma-poly(L-glutamic acid) and epsilon-poly(L-lysine)
Microbiology (Reading) 2009 Sep;155(Pt 9):2988-2993.PMID:19542003DOI:10.1099/mic.0.029694-0.
The poly(amino acid)s gamma-poly(DL-Glutamic acid) (gPGA) and epsilon-poly(l-lysine) (ePL) are known to be natural linear poly(amino acid)s secreted by Bacillus spp. and Streptomyces spp., respectively. In this study, a Streptomyces strain producing both ePL and gPGA was identified. Mass spectrometry and other analyses revealed that the gPGA is a mixture of oligomers consisting of 10-13 l-glutamic acid residues linked by isopeptide bonds. In contrast to the known Bacillus gPGA, the glutamic acid oligomers have a cyclodehydrated structure in each molecule. We previously reported that the ePL molecules secreted by the same Streptomyces strain disperse only slightly in an agar culture plate, as though they were larger molecules. This phenomenon is explicable by the observed polyion complex formation between the glutamic acid oligomers and ePLs. The glutamic acid oligomers control the ePL's dispersion, which would also affect the spatial distribution of the ePL's antimicrobial activity. Therefore, gene clustering or common use of the gene was presumed for biosynthesis of the two poly(amino acid)s. However, no gene for biosynthesis of the glutamic acid oligomer was found in the neighbouring region of that for ePL biosynthesis, and the glutamic acid oligomer was produced by a mutant in which the ePL biosynthetic gene was inactivated by gene disruption.
History of glutamate production
Am J Clin Nutr 2009 Sep;90(3):728S-732S.PMID:19640955DOI:10.3945/ajcn.2009.27462F.
In 1907 Kikunae Ikeda, a professor at the Tokyo Imperial University, began his research to identify the umami component in kelp. Within a year, he had succeeded in isolating, purifying, and identifying the principal component of umami and quickly obtained a production patent. In 1909 Saburosuke Suzuki, an entrepreneur, and Ikeda began the industrial production of monosodium l-glutamate (MSG). The first industrial production process was an extraction method in which vegetable proteins were treated with hydrochloric acid to disrupt peptide bonds. l-Glutamic acid hydrochloride was then isolated from this material and purified as MSG. Initial production of MSG was limited because of the technical drawbacks of this method. Better methods did not emerge until the 1950s. One of these was direct chemical synthesis, which was used from 1962 to 1973. In this procedure, acrylonitrile was the starting material, and optical resolution of DL-Glutamic acid was achieved by preferential crystallization. In 1956 a direct fermentation method to produce glutamate was introduced. The advantages of the fermentation method (eg, reduction of production costs and environmental load) were large enough to cause all glutamate manufacturers to shift to fermentation. Today, total world production of MSG by fermentation is estimated to be 2 million tons/y (2 billion kg/y). However, future production growth will likely require further innovation.
The existence region and composition of a polymer-induced liquid precursor phase for DL-Glutamic acid crystals
Phys Chem Chem Phys 2012 Jan 14;14(2):914-9.PMID:22121508DOI:10.1039/c1cp21862j.
The existence region of a polymer-induced liquid precursor (PILP) phase for crystals of an organic compound (DL-Glutamic acid, Glu) was determined for the first time in the phase diagram of the Glu-polyethyleneimine-water-ethanol system. The existence region and the amount of PILP phase relative to the thermodynamically stable crystal phase were very small. Other phases detected in the phase diagram were coacervates, homogenous mixtures, and crystals obtained via a clear solution. The PILP phase is rich in the polymeric additive, which helps to explain the long induction period of PILP before crystallization occurs. Volume measurements indicated that its amount is <<1 vol%, showing that this precursor phase is only a minor component.