62-57-7

Basic information

• Product Name: 2-Aminoisobutyric Acid
• Synonyms: N-ME-ALANINE;N-ME-ALA-OH;RARECHEM EM WB 0051;DL-2-AMINO-ISO-BUTYRIC ACID;H-2-AMINOISOBUTYRIC ACID;H-ALA(ME)-OH;H-AIB-OH;H-ALPHA-METHYLALANINE
• CAS NO: 62-57-7
• Molecular Formula: C₄H₉NO₂
• Molecular Weight: 103.12
• EINECS: 200-544-0
• Product Categories: Pharmaceutical intermediate;Imidazoles ,Homopiperidines
• Mol File: 62-57-7.mol

Chemical Properties

• Melting Point: ≥300 °C
• Boiling Point: 193.35°C (rough estimate)
• Flash Point: 77.4 °C
• Appearance: White/Crystalline Powder
• Density: 1.1602 (rough estimate)
• Vapor Pressure: 0.108mmHg at 25°C
• Refractive Index: 1.4183 (estimate)
• Storage Temp.: Store at RT.
• Solubility: SOLUBLE
• PKA: 2.36(at 25℃)
• Water Solubility: SOLUBLE
• Merck: 14,445
• BRN: 506496
• CAS DataBase Reference: 2-Aminoisobutyric Acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Aminoisobutyric Acid(62-57-7)
• EPA Substance Registry System: 2-Aminoisobutyric Acid(62-57-7)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: AY7000000
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 62-57-7(Hazardous Substances Data)

Usage

Uses

Used in Diagnostics:
2-Aminoisobutyric acid is used as a diagnostic tool for predicting type II diabetes. The level of alanine aminotransferases, which are regulated by the alanine cycle and include 2-methylalanine as a derivative, can be used to predict the likelihood of developing this condition.
Used in Bioassays:
Due to its non-metabolizable nature in most organisms, except for a few bacteria, 2-Aminoisobutyric acid is utilized in bioassays for various applications.
Used in Pharmaceutical Industry:
2-Aminoisobutyric acid is a non-protein amino acid found in some antibiotics, where it acts as a strong helix inducer in peptides, contributing to the development and effectiveness of these medications.
Used in Research and Development:
As a component of the alanine cycle and a derivative of alanine, 2-Aminoisobutyric acid plays a role in research and development related to amino acid metabolism, protein synthesis, and the understanding of various biological processes.

source

2-aminoisobutyric acid is a rare, non-protein amino acid and end-product of pyrimidine metabolism, excreted in urine and found in some antibiotics of fungal origin. With the exception of a few bacteria, it is non-metabolisable, and therefore used in bioassays. It derives from a propionic acid and an isobutyric acid.

Synthesis Reference(s)

The Journal of Organic Chemistry, 29, p. 1148, 1964 DOI: 10.1021/jo01028a036

Purification Methods

Crystallise the acid from aqueous EtOH and dry it at 110o. [Zelinski & Stadnikoff Chem Ber 39 1726 1906, Beilstein

InChI:InChI=1/C4H9NO2/c1-4(2,5)3(6)7/h5H2,1-2H3,(H,6,7)

Upstream product

• 594-58-1 2-chloro-2-methylpropanoic acid 
• 13922-03-7 2,2'-iminobis(2-methylpropionitrile) 
• 57224-51-8 N-benzoyl-2-methylalanine 
• 77-71-4 5,5-dimethyl-imidazolidine-2,4-dione 
• 151-50-8 potassium cyanide 
• 124-68-5 2-Amino-2-methyl-1-propanol 
• 98140-95-5 2-azido-2-methylpropanoic acid ethyl ester 
• 603-35-0 triphenylphosphine 
• 74-90-8 hydrogen cyanide 
• 67-64-1 acetone 
• 71680-52-9 ammonium cyanide 
• 19355-69-2 2-amino-2-cyanopropane 
• 16252-90-7 2-amino-2-methylpropanamide 
• 76600-38-9 P₁₆₈ 

Downstream Products

• 67-64-1 acetone 
• 4512-46-3 3,3,6,6-tetramethyl-2,5-dioxopiperazine 
• 14463-79-7 2-methyl-2-phthalimidopropanoic acid 
• 5362-00-5 N-acetyl-α,α-dimethylglycine 
• 120880-54-8 5,5-dimethyl-2-thioxo-3-p-tolyl-imidazolidin-4-one 
• 57224-51-8 N-benzoyl-2-methylalanine 
• 21083-30-7 5,5-dimethyl-3-phenyl-2-thioxo-imidazolidin-4-one 
• 95038-11-2 N_α-monochloroacetyl-α-aminoisobutyric acid 
• 13257-67-5 2-amino-2-methylpropionic acid methyl ester 
• 15028-41-8 methyl 2-aminoisobutyrate hydrochloride 
• 5839-88-3 4,4-dimethyloxazolidine-2,5-dione 
• 220022-94-6 2-(dimethylamino)-2-methylpropanoic acid 
• 17288-15-2 ethyl 2-aminoisobutyrate hydrochloride 
• 38605-63-9 N-carbamoyl-α-aminoisobutyric acid 

Relevant articles and documents

Preparation method of 2-methylalanine

The invention specifically discloses a preparation method of 2-methylalanine, belonging to the technical field of organic synthesis. The method comprises the following steps: condensing 2,2-dimethoxypropane serving as a raw material with tert-butyl sulfinamide or tert-butyl carbamate to generate Schiff base, then carrying out nucleophilic addition on the Schiff base and sodium cyanide or potassium cyanide under the action of phase transfer catalysis and ammonium chloride, and then adding acid to hydrolyze cyano groups so as to obtain 2-methylalanine. According to the invention, the used raw materials are easily to obtain and low in price; process flow is simple and convenient; reaction conditions are mild; requirements on equipment are low; total yield is as high as 80-83%; and the purity of the prepared 2-methylalanine is more than 99.6%.

Aziridine Formation by a FeII/α-Ketoglutarate Dependent Oxygenase and 2-Aminoisobutyrate Biosynthesis in Fungi

Aziridine is a characteristically reactive molecule with increased bioactivity due to its strained ring structure. Here, we investigated the biosynthesis of 2-aminoisobutyric acid (AIB) in Penicillium, and successfully reconstituted the three-step biosynthesis from L-Val to AIB in vitro. This previously unknown aziridine formation pathway proceeded with the non-heme iron and α-ketoglutarate-dependent (FeII/αKG) oxygenase TqaL, followed by aziridine ring opening by the haloalkanoic acid dehalogenase (HAD)-type hydrolase TqaF, and subsequent oxidative decarboxylation by the NovR/CloR-like non-heme iron oxygenase TqaM. Furthermore, the X-ray crystal structure of the C?N bond forming FeII/αKG oxygenase TqaL was solved at 2.0 ? resolution. This work presents the first molecular basis for aziridine biogenesis, thereby expanding the catalytic repertoire of the FeII/αKG oxygenases. We also report the unique aziridine ring opening by a HAD-type hydrolase and the remarkable oxidative decarboxylation by a non-heme iron oxygenase to produce AIB.

General Synthesis of Amino Acid Salts from Amino Alcohols and Basic Water Liberating H2

An atom-economical and environmentally friendly method to transform amino alcohols to amino acid salts using just basic water, without the need of pre-protection or added oxidant, catalyzed by a ruthenium pincer complex, is developed. Water is the solvent, the source of the oxygen atom of the carboxylic acid group, and the actual oxidant, with liberation of dihydrogen. Many important and useful natural and unnatural amino acid salts can be produced in excellent yields by applying this new method.

FUNCTIONALIZED FLUORINE CONTAINING PHTHALOCYANINE MOLECULES

Functionalized fluorine containing phthalocyanine molecules, methods of making, and methods of use in diagnostic applications and disease treatment are disclosed herein. In some embodiments, the fluorine containing phthalocyanine molecules are functionalized with a reactive functional group or at least one cancer-targeting ligand (CTL). The CTL can facilitate more efficient binding and/or internalization to a cancer cell than to a healthy cell. The CTL can inhibit expression of oncoprotein in some embodiments. The pthalocyanine moiety can be used in diagnostic applications, such as fluorescence labeling of a cancer cell, and/or treatment applications, such as catalyzing formation of a reactive oxygen species (ROS) which can contribute to cell death of a cancer cell.

Meteorites as catalysts for prebiotic chemistry

From outer space: Twelve meteorite specimens, representative of their major classes, catalyse the synthesis of nucleobases, carboxylic acids, aminoacids and low-molecular-weight compounds from formamide (see figure). Different chemical pathways are identified, the yields are high for a prebiotic process and the products come in rich and composite panels.

Trichoderins, novel aminolipopeptides from a marine sponge-derived Trichoderma sp., are active against dormant mycobacteria

Three new aminolipopeptides, designated trichoderins A (1), A1 (2), and B (3), were isolated from a culture of marine sponge-derived fungus of Trichoderma sp. as anti-mycobacterial substances with activity against active and dormant bacilli. The chemical structures of trichoderins were determined on the basis of spectroscopic study. Trichoderins showed potent anti-mycobacterial activity against Mycobacterium smegmatis, Mycobacterium bovis BCG, and Mycobacterium tuberculosis H37Rv under standard aerobic growth conditions as well as dormancy-inducing hypoxic conditions, with MIC values in the range of 0.02-2.0 μg/mL.

Asperelines A-F, peptaibols from the marine-derived fungus Trichoderma asperellum

Fermentation of the marine-derived fungus Trichoderma asperellum, collected from the sediment of the Antarctic Penguin Island, resulted in the isolation of six new peptaibols named asperelines A-F (1-6), which are characterized by an acetylated N-terminus and a C-terminus containing an uncommon prolinol residue. Structures were determined by extensive 1D and 2D NMR (1H- 1H COSY, HMQC, HMBC, NOESY) spectroscopic data analysis combined with ESIMS/MS fragmentation. The absolute configurations of the amino acid residues possessing a chiral R-carbon and of the prolinol residue were determined to be L and S, respectively, using a new method of 1H NMR spectroscopic comparison of complexes formed between the chiral reagent Ru(D 4-Por*)CO and amino acids derived from the peptaibols with those formed with reference standards.

Versatile synthesis of free and N-benzyloxycarbonyl-protected 2,2-disubstituted taurines

An effective and versatile method was developed to synthesize N-benzyloxycarbonyl-protected and free 2,2-disubstituted taurines. Several novel 2,2-disubstituted taurines, including aliphatic/aromatic and cyclic/acyclic derivatives, were obtained, which demonstrates the generality of this method. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Growth Hormone Secretagogue Receptor 1A Ligands

The present invention relates to new growth hormone secretagogue receptor 1A (GHS-R 1A) ligands, and pharmaceutical compositions comprising any of the new GHS-R1 A ligands. The ligands are suitable for a wide range of applications, and thus the present invention also relates to use of the GHS-R1 A ligands according to the present invention in the manufacture of a medicament for the treatment of an individual in need thereof. In another aspect, the present invention relates to a method of treatment of an individual in need thereof, comprising administering to said individual one or more of the GHS-R1A ligands disclosed herein, such as e.g. for treatment of cancer cachexia.

Influence of solvent viscosity on the rate of hydrolysis of dipeptides by carboxypeptidase Y

The influence of solvent viscosity on the rate of enzymatic hydrolysis of a series of dipeptides (Z-Phe-Gly, Z-Phe-Sar, Z-Phe-Ala, Z-Phe-NMeAla, Z-Phe-Aib and Z-Phe-Pro) by carboxypeptidase Y was investigated. The effect of solvent viscosity on the enzymatic hydrolysis revealed that whereas all Kcat values decreased with viscosity, those of the N-alkyl peptides decreased more than those of the N-H peptides. The kinetic behaviour implies the involvement of conformational changes of the enzyme in terms of the 'induced-fit' process. Copyright