(2R)-2-ammonio-3-methylbutanoate

Base Information

• Chemical Name: (2R)-2-ammonio-3-methylbutanoate
• CAS No.: 640-68-6
• Molecular Formula: C5H11NO2
• Molecular Weight: 117.148
• Hs Code.: 2922.49
• Mol file: 640-68-6.mol

Synonyms:(2R)-2-ammonio-3-methylbutanoate;(2R)-2-azaniumyl-3-methyl-butanoate;D-valine zwitterion;D-2-amino-3-methylbutyric acid;CHEBI:74338;2-Amino-3-methylbutanoic acid(D);A828684;A834630

Chemical Property of (2R)-2-ammonio-3-methylbutanoate

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 0.0633mmHg at 25°C
• Melting Point: >295 °C (subl.)(lit.)
• Refractive Index: -27 ° (C=8, 6mol/L HCl)
• Boiling Point: 213.6 °C at 760 mmHg
• PKA: 2.37±0.10(Predicted)
• Flash Point: 83 °C
• PSA: 63.32000
• Density: 1.063 g/cm³
• LogP: 0.75460
• Storage Temp.: Store at RT.
• Solubility.: 56 g/L (20°C)
• Water Solubility.: 56 g/L (20 ºC)
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 117.078978594
• Heavy Atom Count: 8
• Complexity: 84.9

Purity/Quality:

99.4% ^*data from raw suppliers

D-Valine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(=O)[O-])[NH3+]
• Isomeric SMILES: CC(C)[C@H](C(=O)[O-])[NH3+]
• 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.
• Uses: 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. 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. 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.

Technology Process of (2R)-2-ammonio-3-methylbutanoate

There total 127 articles about (2R)-2-ammonio-3-methylbutanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

4-<(2R,5S)-2,5-Dihydro-2-isopropyl-3,6-dimethoxy-5-pyrazinyl>butylamine (129243-87-4) → D-Val-OH (640-68-6,25609-85-2,7004-03-7,921-10-8) + L-Lysine hydrochloride (657-27-2,10098-89-2,26124-78-7)

Guidance literature:

With hydrogenchloride; at 70 ℃;

Reference yield:

itralamide B (1187486-25-4) → N-methylalanine (3913-67-5) + D-Val-OH (640-68-6,25609-85-2,7004-03-7,921-10-8) + (2S,3R)-3-hydroxy-2-(methylamino)butanoic acid (2812-28-4) + N-methylalanylvaline + N-methylphenylalanylvaline + N-methyl-D-phenylalanine (56564-52-4)

Guidance literature:

With hydrogenchloride; water; at 110 ℃; for 18.5h;

DOI:10.1021/np900173d

Reference yield:

(4aS,10aR,13S,19aR,21aS,26bR,27aS,30R)-24-chloro-2,3,4,4a,8,9,10,10a,12,13,17,18,19,19a,22,26b,27,27a,29,30-icosahydro-25,26b-dihydroxy-12,13-dimethyl-30-(propan-2-yl)-7H,21aH-tripyridazino[1’’,6’’:10’,11’;1’’’,6’’’:16’,17’;1’’’’,6’’’’:7’,8’] [1,4,7,10,13,16]hexaazacyclooctadecino[1’,2’:1,5]pyrrolo[2,3-b]indole-5,11,14,20,28,31(1H,16H)-hexone (1400276-81-4) → N-methyl-D-alanine (29475-64-7) + D-Val-OH (640-68-6,25609-85-2,7004-03-7,921-10-8) + (2S,3aR,8aR)-6-chloro-1,2,3,3a,8,8a-hexahydro-3a,5-dihydroxypyrrolo-[2,3-b]indole-2-carboxylic acid + (3S)-hexahydropyridazine-3-carboxylic acid

Guidance literature:

With hydrogenchloride; water; at 110 ℃; for 24h;

DOI:10.1002/cbdv.201100364

upstream raw materials:

D,L-valine

N-formylvaline

N-chloroacetyl-D-valine

2-iodo-propane

Downstream raw materials:

(R)-N-phthaloylvaline

N-(N-benzoyl-D-valyl)-D-valine

N-(N-benzoyl-L-valyl)-D-valine

(R)-2-Hydroxy-3-methylbutyric acid

Refernces

• 1、 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. "Single-Cell-Based Screening and Engineering of d -Amino Acid Amidohydrolases Using Artificial Amidophenol Substrates and Microbial Biosensors". . p. 1203 - 1211. Retrieved 2022/01/27.
• 2、 Chao, Rong,Hou, Xue-Mei,Xu, Wei-Feng,Hai, Yang,Wei, Mei-Yan,Wang, Chang-Yun,Gu, Yu-Cheng,Shao, Chang-Lun. "Targeted Isolation of Asperheptatides from a Coral-Derived Fungus Using LC-MS/MS-Based Molecular Networking and Antitubercular Activities of Modified Cinnamate Derivatives". . p. 11 - 19. Retrieved 2021/01/14.