640-68-6 Usage
Description
D-Valine, the D-form of valine, is a non-proteinogenic isomer of the essential amino acid L-Valine. It is a white crystal with a melting point of over 295°C (sublimation) and exhibits optical activity with a specific rotation of [α]25 = +27.35°. D-Valine is soluble in water and very slightly soluble in ethanol. It serves as an important organic chiral source and plays a significant role in various applications across different industries.
Uses
Used in Pesticide Synthesis:
D-Valine is used as a key component in the synthesis of efficient pesticides such as pyrethroids permethrin and chlorofluorocarbons amyl. The produced valine insecticide permethrin is a broad-spectrum and promising insecticide and acaricide, effective through touch-killing and stomach poisoning by inhibiting the activity of related enzyme systems in insects. This application aids in the effective control of major pests, including Lepidoptera and Diptera, in corps like cotton, fruit trees, and vegetables.
Used in Biochemical Research:
D-Valine is utilized in biochemical research for various purposes. It can inhibit the growth of fibroblasts and is applied in studies investigating its influence on the morphology and function of pulmonary artery endothelial cells. Additionally, it serves as an important raw material for chiral drugs, such as those used in the synthesis of antineoplastic, anti-diabetes, and anti-diabetes complications medications.
Used in Pharmaceutical Industry:
D-Valine is an essential chiral source in the pharmaceutical industry, playing an irreplaceable role in the asymmetric synthesis of certain chiral compounds. It is primarily used for the production of new broad-spectrum antibiotics, such as D-valinol, and as a valine protective agent during peptide synthesis processes.
Used in Chiral Synthesis:
As an optically active organic acid, D-Valine is used as a chiral source for chiral synthesis in the pharmaceutical industry, contributing to the development of chiral pharmaceuticals, chiral additives, and chiral auxiliaries.
Used in the Production of Fluvalinate:
D-Valine serves as an intermediate in the production of fluvalinate, an insecticide used in animal healthcare.
Used in the Synthesis of Synthetic Sweeteners:
D-Valine is also utilized in the synthesis of Alatan, a synthetic sweetener.
Used in Culture Media for Selective Growth:
D-Valine acts as a selective agent in epithelial cell cultures, as it inhibits cells that lack the enzyme D-amino acid oxidase. It has been shown to inhibit the proliferation of contaminating fibroblasts in smooth muscle cells from human myometrium, thus allowing selective growth of epithelial cells.
Used in Anticancer Research:
D-Valine solution has demonstrated tumor growth inhibition and improvements in the nutritional status of AH109A hepatoma-bearing rats, indicating its potential use in anticancer research and applications.
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.
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.
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.
Targeted Isolation of Asperheptatides from a Coral-Derived Fungus Using LC-MS/MS-Based Molecular Networking and Antitubercular Activities of Modified Cinnamate Derivatives
Chao, Rong,Hou, Xue-Mei,Xu, Wei-Feng,Hai, Yang,Wei, Mei-Yan,Wang, Chang-Yun,Gu, Yu-Cheng,Shao, Chang-Lun
, p. 11 - 19 (2021/01/14)
Under the guidance of MS/MS-based molecular networking, four new cycloheptapeptides, namely, asperheptatides A-D (1-4), were isolated together with three known analogues, asperversiamide A-C (5-7), from the coral-derived fungus Aspergillus versicolor. The planar structures of the two major compounds, asperheptatides A and B (1 and 2), were determined by comprehensive spectroscopic data analysis. The absolute configurations of the amino acid residues were determined by advanced Marfey's method. The two structurally related trace metabolites, asperheptatides C and D (3 and 4), were characterized by ESI-MS/MS fragmentation methods. A series of new derivatives (8-26) of asperversiamide A (5) were semisynthesized. The antitubercular activities of 1, 2, and 5-26 against Mycobacterium tuberculosis H37Ra were also evaluated. Compounds 9, 13, 23, and 24 showed moderate activities with MIC values of 12.5 μM, representing a potential new class of antitubercular agents.