640-68-6 Usage
Description
D-valine is the D-form of valine, being the non-proteinogenic isomer of valine. It can be supplemented into the cell culture for selectively inhibition of cell proliferation through inhibiting cells that are deficient in the enzyme D-amino acid oxidase. It has also been used to inhibit fibroblast growth while allowing the selective growth of epithelial cells.
Valine
Valine is one kinds of the essential amino acids for human being with the requirement of adult males being 10mg/(kg ? d) (FAO/WHO1973). Being lack of this product can cause neurological disorders, reduction of developmental ability as well as anemia.
Valine is one of the 20 amino acids that form protein with its chemical name being 2-amino-3-methyl-butyric acid. It belongs to branched chain amino acids and is one of the eight kinds of essential amino acids and carbohydrate-producing amino acids of human body. It works together with the other two high-concentration amino acids (leucine and isoleucine) to promote the normal growth of body, tissue repair, regulate blood sugar, and provide the energy needed. When participating in intense physical activity, valine can provide extra energy to the muscles for producing glucose in order to prevent of muscle weakness. It also helps remove excess nitrogen (potentially toxic) from the liver, and transport nitrogen to all of the rest parts of the body.
Valine is an essential amino acid, which means that the human body itself cannot synthesize themselves so that it must be replenished through dietary sources. Its natural food sources include cereals, dairy products, mushrooms, mushrooms, peanuts, soy protein and meat. D-Valine is also found in some actinomyces (such as valeriana). While most people can get sufficient quantities of D-valine from the diet, however, there are still many cases about valine deficiency. Upon being lack of sufficient valine, rats get limb tremors due to disorder of the central nervous system as well as ataxia. Through dissecting slices of brain tissue, it was found about the phenomenon of the red nucleus cell degeneration. Owing to the liver function damage of patients with advanced cirrhosis of the liver, hyperinsulinemia is easy to occur, resulting in the reduction of branched chain amino acids in the blood. The ratio of branched-chain amino acids over aromatic amino acids decreases from 3.0-3.5 (normal body) to 1.0-1.5. It is common for using injection of branched chain amino acids such as valine in the treatment of liver failure, and the damage of alcoholism and drug abuse on these organs.
Uses
Different sources of media describe the Uses of 640-68-6 differently. You can refer to the following data:
1. 1. D-valine can be used for the synthesis of newly efficient pesticide: pyrethroids permethrin and chlorofluorocarbons amyl because of its own biochemical characteristics. The produced valine insecticide permethrin is a broad-spectrum and promising insecticide acaricide which can have effects of touch-killing and stomach poisoning through inhibiting the activity of related enzyme systems of insects. In this way, it can be used for effectively controlling of major pests including Lepidoptera and Diptera in corps such as cotton, fruit trees, and vegetables. D-valine is also widely used in biomedical research.
For example, it can be used to inhibit the growth of fibroblasts, and be applied to the studies on its influence on the morphology and function of pulmonary artery endothelial cells. D-valine are also important raw materials as chiral drugs for example it may be used for the synthesis of antineoplastic drugs, anti-diabetes and its complications drugs. With the expansion of the applications fields as well as market demanding of D-valine, the preparation of D-valine will become a hot research field on amino acid.
2. D-Valine is an important organic chiral source which is mainly used in fields such as chiral pharmaceuticals, chiral additive, and chiral auxiliary and other areas. It can also be used as the chiral source of chiral synthesis in the pharmaceutical industry. As an optically active organic acid, it plays an irreplaceable role in the asymmetric synthesis of certain chiral compounds. It is currently mainly used for the production of new broad-spectrum antibiotic, D-valinol, and valine protective agent during the process of peptide synthesis.
3. D-valine is the intermediates for fluvalinate.
4. It is used as a pharmaceutical raw materials and pharmaceutical intermediates, and can also be used for synthetic sweeteners Alatan.
5. It can also be used for biochemical research.
The above information is edited by the lookchem of Dai Xiongfeng.
2. D-Valine is an isomer of the essential amino acid L-Valine. D-Valine has been used as a selective agent in epithelial cells in culture since it inhibits cells that lack the enzyme D-amino acid oxidase
. D-Valine has also been shown to inhibit proliferation of contaminating fibroblasts in smooth muscle cells from human myometrium. D-Valine solution showed tumor growth inhibition and improvements of
the nutritional status in AH109A hepatoma-bearing rats.
3. D-Valine is an isomer of the essential amino acid L-Valine. D-Valine has been used as a selective agent in epithelial cells in culture since it inhibits cells that lack the enzyme D-amino acid oxidase. D-Valine has also been shown to inhibit proliferation of contaminating fibroblasts in smooth muscle cells from human myometrium. D-Valine solution showed tumor growth inhibition and improvements of the nutritional status in AH109A hepatoma-bearing rats.
Chemical Properties
Different sources of media describe the Chemical Properties of 640-68-6 differently. You can refer to the following data:
1. White crystal, m.p.> 295 °C (sublimation), [α] 25 = 27.35°; it is soluble in water and very slightly soluble in ethanol.
2. white to off-white crystalline powder
Production methods
1. DL-Acetyl-methionine is used as the raw material. It undergoes acylase splitting, and further hydrochloric acid acidification to have D-valine crystals precipitated; refined product is finally obtained through recrystallization.
2. The preparation method is to use 2-isopropyl-acetyl ethyl to react with benzene diazonium to get corresponding hydrazine compound, and then further reduce it to valine in zinc-ethanol solution and finally go through chemical or biological split.
References
http://www.sigmaaldrich.com/catalog/product/sigma/v1255?lang=en®ion=US
Gilbert, S. F., and B. R. Migeon. "D-valine as a selective agent for normal human and rodent epithelial cells in culture." Cell 5.1(1975):11.
Hongpaisan, J. "Inhibition of proliferation of contaminating fibroblasts by D-valine in cultures of smooth muscle cells from human myometrium. " Cell Biology International 24.1(2000):1.
Definition
ChEBI: The D-enantiomer of valine.
General Description
L-Valine is an essential non-polar amino acid. D-Valine is the non-proteinogenic isomer of valine.
Biochem/physiol Actions
D-valine is used in cell culture as a selective inhibitor of cell proliferation, wherein it inhibits cells that lack the enzyme D-amino acid oxidase. Historically D-valine has been used to inhibit fibroblast growth while allowing selective growth of epithelial cells.
Check Digit Verification of cas no
The CAS Registry Mumber 640-68-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,4 and 0 respectively; the second part has 2 digits, 6 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 640-68:
(5*6)+(4*4)+(3*0)+(2*6)+(1*8)=66
66 % 10 = 6
So 640-68-6 is a valid CAS Registry Number.
InChI:InChI=1/C5H11NO2/c1-3(2)4(6)5(7)8/h3-4H,6H2,1-2H3,(H,7,8)/t4-/m1/s1
640-68-6Relevant articles and documents
Single-Cell-Based Screening and Engineering of d -Amino Acid Amidohydrolases Using Artificial Amidophenol Substrates and Microbial Biosensors
An, Jung-Ung,Kim, Haseong,Kwon, Kil Koang,Lee, Dae-Hee,Lee, Hyewon,Lee, Jin-Young,Lee, Seung-Goo,Park, Sung Hyun,Rha, Eugene,Yeom, Soo-Jin
, p. 1203 - 1211 (2022/01/27)
Enantiomerically pure d-amino acids are important intermediates as chiral building blocks for peptidomimetics and semisynthetic antibiotics. Here, a transcriptional factor-based screening strategy was used for the rapid screening of d-stereospecific amino acid amidase via an enzyme-specific amidophenol substrate. We used a d-threonine amidophenyl derivative to produce 2-aminophenol that serves as a putative enzyme indicator in the presence of d-threonine amidases. Comparative analyses of known bacterial species indicated that several Bacillus strains produce amidase and form putative indicators in culture media. The estimated amidase was cloned and subjected to rapid directed evolution through biosensor cells. Consequently, we characterized the F119A mutation that significantly improved the catalytic activity toward d-alanine, d-threonine, and d-glutamate. Its beneficial effects were confirmed by higher conversions and recurrent applications of the mutant enzyme, compared to the wild-type. This study showed that rapid directed evolution with biosensors coupled to designed substrates is useful to develop biocatalytic processes.
Inherently chiral dialkyloxy-calix[4]arene acetic acids as enantiodiscriminating additives for high-performance liquid chromatography separation of d,l-amino acids
Kalchenko, Olga I.,Trybrat, Oleksandr O.,Yesypenko, Oleksandr A.,Dyakonenko, Viktoriya V.,Shishkina, Svitlana V.,Kalchenko, Vitali I.
, p. 722 - 730 (2021/08/26)
Inherently chiral dialkyloxy-calix[4]arene acetic acids with asymmetric placement of substituents on the lower rim of the macrocycle were first studied as enantiodiscriminating additives to the mobile phase MeCN/H2O/HCOOH (75/25/0.02 by volume) in the high-performance liquid chromatography (HPLC) separation of d,l-alanine and d,l-valine on the achiral stationary phase ZORBAX Original CN. The dependence of enantio-binding properties on the position of alkyl groups is demonstrated. The highest resolution (1.65) and enantioselectivity (1.80) were obtained for the 1,2-dipropyloxy-calix[4]arene acetic acid.
A new amide from the marine sponge Haliclona baeri
Cui, Le-Zhi,Lei, Yu,Liao, Xiao-Jian,Wang, Can-Bin,Xiao, Yan-Fang,Xu, Jia-Yi,Xu, Shi-Hai,Zhao, Bing-Xin
supporting information, (2021/07/06)
A new amide, baeriamide (1), along with nine known diketopiperazines (2-10), was isolated from the marine sponge Haliclona baeri. Their structures were identified by the means of UV, IR, MS and NMR. The absolute configuration of 1 was established by Marfey’s method and comparing the specific optical rotation with the known compound HCO-Val-Gly methyl ester. Compound 1 was derived from dehydration of formylated L-valine with γ-amino-butanoic acid methyl ester. Compounds 2-10 were isolated from the genus of Haliclona for the first time. The absolute confirmation of 7 was confirmed first by the means of single-crystal X-ray diffraction. The cytotoxic, antibacterial, antiviral and antifouling activities of these compounds were also tested. However, none of them exhibited significant bioactivities.