N-Methyl-D-glutamine
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| Category | Others |
| Catalog number | BBF-05235 |
| CAS | 862504-01-6 |
| Molecular Weight | 160.17 |
| Molecular Formula | C6H12N2O3 |
| Purity | ≥95% by HPLC |
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Specification
| Related CAS | 300560-56-9 (L-configuration) |
| Synonyms | N-Me-D-Gln-OH; N2-Methyl-D-glutamine; methyl-D-glutamine; Nalpha-Methyl-D-glutamine |
| Storage | Store at -20°C |
| IUPAC Name | (2R)-5-amino-2-(methylamino)-5-oxopentanoic acid |
| Canonical SMILES | CNC(CCC(=O)N)C(=O)O |
| InChI | InChI=1S/C6H12N2O3/c1-8-4(6(10)11)2-3-5(7)9/h4,8H,2-3H2,1H3,(H2,7,9)(H,10,11)/t4-/m1/s1 |
| InChI Key | KSZFSNZOGAXEGH-SCSAIBSYSA-N |
Properties
| Boiling Point | 427.5±40.0°C at 760 mmHg |
| Density | 1.2±0.1 g/cm3 |
Reference Reading
1. Production of l-Theanine by Escherichia coli in the Absence of Supplemental Ethylamine
Ryota Hagihara, Shoto Ohno, Mikiro Hayashi, Kazuhiko Tabata, Hirofumi Endo Appl Environ Microbiol. 2021 May 11;87(11):e00031-21. doi: 10.1128/AEM.00031-21. Print 2021 May 11.
l-Theanine is a nonproteinogenic amino acid present almost exclusively in tea plants and is beneficial for human health. For industrial production, l-theanine is enzymatically or chemically synthesized from glutamine/glutamate (or a glutamine/glutamate derivative) and ethylamine. Ethylamine is extremely flammable and toxic, which complicates and increases the cost of operational procedures. To solve these problems, we developed an artificial biosynthetic pathway to produce l-theanine in the absence of supplemental ethylamine. For this purpose, we identified and selected a novel transaminase (NCBI:protein accession number AAN70747) from Pseudomonas putida KT2440, which catalyzes the transamination of acetaldehyde to produce ethylamine, as well as γ-glutamylmethylamide synthetase (NCBI:protein accession number AAY37316) from Pseudomonas syringae pv. syringae B728a, which catalyzes the condensation of l-glutamate and ethylamine to produce l-theanine. Expressing these genes in Escherichia coli W3110S3GK and enhancing the production capacity of acetaldehyde and l-alanine achieved successful production of l-theanine without ethylamine supplementation. Furthermore, the deletion of ggt, which encodes γ-glutamyltranspeptidase (EC 2.3.2.2), achieved large-scale production of l-theanine by attenuating its decomposition. We show that an alanine decarboxylase-utilizing pathway represents a promising route for the fermentative production of l-theanine. Our study reports efficient methods to produce l-theanine in the absence of supplemental ethylamine.IMPORTANCE l-Theanine is widely used in food additives and dietary supplements. Industrial production of l-theanine uses the toxic and highly flammable precursor ethylamine, raising production costs. In this study, we used Escherichia coli to engineer two biosynthetic pathways that produce l-theanine from glucose and ammonia in the absence of supplemental ethylamine. This study establishes a foundation for safely and economically producing l-theanine.
2. Efficient fermentative production of L-theanine by Corynebacterium glutamicum
Hongkun Ma, Xiaoguang Fan, Ningyun Cai, Dezhi Zhang, Guihong Zhao, Ting Wang, Rui Su, Meng Yuan, Qian Ma, Chenglin Zhang, Qingyang Xu, Xixian Xie, Ning Chen, Yanjun Li Appl Microbiol Biotechnol. 2020 Jan;104(1):119-130. doi: 10.1007/s00253-019-10255-w. Epub 2019 Nov 27.
L-Theanine is a unique non-protein amino acid found in tea plants that has been shown to possess numerous functional properties relevant to food science and human nutrition. L-Theanine has been commercially developed as a valuable additive for use in food and beverages, and its market is expected to expand substantially if the production cost can be lowered. Although the enzymatic approach holds considerable potential for use in L-theanine production, demand exists for developing more tractable methods (than those currently available) that can be implemented under mild conditions and will reduce operational procedures and cost. Here, we sought to engineer fermentative production of L-theanine in Corynebacterium glutamicum, an industrially safe host. For L-theanine synthesis, we used γ-glutamylmethylamide synthetase (GMAS), which catalyzes the ATP-dependent ligation of L-glutamate and ethylamine. First, distinct GMASs were expressed in C. glutamicum wild-type ATCC 13032 strain and GDK-9, an L-glutamate overproducing strain, to produce L-theanine upon ethylamine addition to the hosts. Second, the L-glutamate exporter in host cells was disrupted, which markedly increased the L-theanine titer in GDK-9 cells and almost eliminated the accumulation of L-glutamate in the culture medium. Third, a chromosomally gmasMm-integrated L-alanine producer was constructed and used, attempting to synthesize ethylamine endogenously by expressing plant-derived L-serine/L-alanine decarboxylases; however, these enzymes showed no L-alanine decarboxylase activity under our experimental conditions. The optimal engineered strain that we ultimately created produced ~ 42 g/L L-theanine, with a yield of 19.6%, in a 5-L fermentor. This is the first report of fermentative production of L-theanine achieved using ethylamine supplementation.
3. Multicomponent Crystal of Mefenamic Acid and N-Methyl-d-Glucamine: Crystal Structures and Dissolution Study
Erizal Zaini, Lili Fitriani, Risda Yulia Sari, Henni Rosaini, Ayano Horikawa, Hidehiro Uekusa J Pharm Sci. 2019 Jul;108(7):2341-2348. doi: 10.1016/j.xphs.2019.02.003. Epub 2019 Feb 16.
A novel multicomponent crystal (MC) of mefenamic acid (MA) and N-methyl-d-glucamine (MG) had been prepared to improve the physicochemical properties of poorly soluble drugs, and was characterized for its physicochemical properties by powder X-ray diffraction analysis, differential scanning calorimetry thermal analysis, FT-IR spectroscopy, in vitro dissolution rate, and physical stability. In addition, the crystal structure was determined by single-crystal X-ray diffraction analysis. The differential scanning calorimetry thermogram of the MA-MG binary system exhibits a single and sharp endothermic peak at 151.20°C, which was attributed to the melting point of a MC of MA-MG. FT-IR spectroscopy analysis showed the occurrence of solid-state interaction by involving proton transfer between MA and MG. The crystal structure analysis confirmed that MA-MG formed 1:1 ratio salt type MC. The formation of a MC of MA with MG significantly improved the dissolution rate of MA in compared to intact MA, and also the crystal demonstrated a good stability under a high relative humidity. These good properties would be attributed to the layer structure of MA and MG in the crystal.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
