465-58-7

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-2-METHYLBUTYRIC ACID is used as a building block for the synthesis of peptide compounds in the pharmaceutical industry. Its steric hindrance allows for the creation of highly specific and stable peptide structures, which can be tailored for targeted drug delivery and therapeutic applications.
Used in Peptide Synthesis:
2-AMINO-2-METHYLBUTYRIC ACID is used as a key component in the preparation of peptide compounds that comprise highly sterically hindered amino acids. It is synthesized through the reaction of an electron-withdrawing group-protected N-unsubstituted-α,α-disubstituted amino acid with a peptide, followed by N-alkylation. This process enables the development of innovative and effective peptide-based drugs with improved pharmacokinetic properties and therapeutic potential.

Upstream product

• 56247-82-6 α-ethylalanine ethyl ester 
• 74-90-8 hydrogen cyanide 
• 78-93-3 butanone 
• 71680-52-9 ammonium cyanide 
• 151-50-8 potassium cyanide 
• 60307-41-7 2-Methyl-2-{[1-phenyl-meth-(E)-ylidene]-amino}-butyronitrile 
• 5394-36-5 5-ethyl-5-methylimidazolidine-2,4-dione 
• 59209-90-4 (RS)-2-amino-2-methylbutanamide 
• 7647-01-0 hydrogenchloride 
• 50846-37-2 2-amino-2-methylbutyronitrile hydrochloride 
• 139937-98-7 N-(tert-butoxycarbonyl)-2-amino-2-methylbutanoic acid 
• 86960-59-0 N-chloroacetyl-D-isovaline 
• 595-39-1 DL-isovaline 
• 2576-61-6 4-ethyl-4-methyl-2-phenyl-4H-oxazol-5-one 

Downstream Products

• 10196-30-2 (R)-2-amino-2-methylbutan-1-ol 
• 73473-40-2 (2R)-2-amino-2-methylbutanoic acid hydrochloride 
• 123254-58-0 (R)-2-((tert-butoxycarbonyl)amino)-2-methylbutanoic acid 
• 13893-46-4 ethyl (R)-2-amino-2-methylbutyrate 
• 92760-72-0 L-isovalin methyl ester hydrochloride 
• 857478-30-9 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-isovaline 

Relevant academic research and scientific papers

Synthesis of isotope-labeled aminoacids contained in servamycin antibiotic

Approach was developed to a preparative synthesis of isotope-labeled aminoacids contained in servamycin IIB antibiotic. Glutamines labeled with 15N, 13C, and 2H were prepared in 70-80% yield starting with the corresponding labeled glutamic acids under catalysis with the glutamine synthetase enzyme. 15N-2-aminoisohutanoic acid and 15N-isovaline were obtained by Strecker method in 65 and 31% yields respectively. All compounds synthesized were identified and characterized by NMR spectroscopy.

Amino Acid-Derived trans-N-Chloroformylimidazolidinones: Scalable, Stereoselective Synthesis, Structure, and Utility

N-acyl imidazolidinones, which are key intermediates in the stereoselective synthesis of amino acids by "self-regeneration of stereochemistry" methods, are classically made by only moderately diastereoselective methods. We now report that cyclization of pivaldimino-amides with phosgene in the presence of pyridine may be made fully diastereoselective for the trans-N-chloroformylimidazolidinones, and we detail the conformational features of the products. We show that despite the presence of the electrophilic carbamoyl chloride function the products show remarkable stability and may be deprotonated to form enolates with useful reactivity for the synthesis of amino acid derivatives.

Leveraging Peptaibol Biosynthetic Promiscuity for Next-Generation Antiplasmodial Therapeutics

Malaria remains a worldwide threat, afflicting over 200 million people each year. The emergence of drug resistance against existing therapeutics threatens to destabilize global efforts aimed at controlling Plasmodium spp. parasites, which is expected to leave vast portions of humanity unprotected against the disease. To address this need, systematic testing of a fungal natural product extract library assembled through the University of Oklahoma Citizen Science Soil Collection Program has generated an initial set of bioactive extracts that exhibit potent antiplasmodial activity (EC50 25 μM, selectivity index > 250). The unique chemodiversity afforded by these fungal isolates serves to unlock new opportunities for translating peptaibols into a bioactive scaffold worthy of further development.

High-chirality method for selectively synthesizing alpha-disubstituted alpha-amino acid

The invention discloses a high-chirality method for selectively synthesizing alpha-disubstituted alpha-amino acid. The high-chirality method for selectively synthesizing alpha-disubstituted alpha-amino acid is characterized by comprising the following steps: step one, reacting S-tert-butanesulfinyl amide or R-tert-butanesulfinyl amide, R-beta substituted ethyl pyruvate and tetraethyl titanate in atetrahydrofuran solvent to obtain a compound C; step two, reacting the compound C with alkyl substituted magnesium bromide under the catalyzing effect of zinc dimethyl in tetrahydrofuran to obtain acompound E; step three, reacting the compound E under the effect of ammonium chloride and anhydrous hydrogen chloride to obtain a compound F; and step four, hydrolyzing the compound F in an ethanol aqueous solution of sodium hydroxide to obtain hydrochloride of a compound G, and carrying out ion exchange to obtain the compound G. The chiral selective reaction is greatly improved, and the method issimple in process, uses cheap and easily obtained raw materials, is simple and convenient to operate, is quite suitable for industrial mass production, and has quite extensive industrial applicationprospect and market value.

A practical chemoenzymatic synthesis of (R)-isovaline based on the asymmetric hydrolysis of 2-ethyl-2-methyl-malonamide

(R)-Isovaline has potential applications in drug development, and therefore the development of an efficient method for the production of (R)-isovaline is desired. Herein we have investigated the asymmetric hydrolysis of 2-ethyl-2-methyl-malonamide into (S)-2-ethyl-2-methyl-malonamic acid, a useful synthetic intermediate in the production of (R)-isovaline, using CsAM, which is a recombinant amidase originally derived from Cupriavidus sp. KNK-J915. The produced (S)-2-ethyl-2-methyl-malonamic acid (98.6% ee) could be easily converted into (R)-isovaline by the Hofmann rearrangement. Starting from diethyl 2-methylmalonate, we obtained (R)-isovaline (99.1% ee) in 58.6% yield over eight steps, including the CsAM-catalyzed asymmetric hydrolysis of 2-ethyl-2-methyl-malonamide.

SN2 displacement at the quaternary carbon center: A novel entry to the synthesis of α,α-disubstituted α-amino acids This Letter is dedicated to the late Professor Harry Wasserman, a great chemist as well as a splendid artist

A novel method for the SN2 reaction on quaternary carbon atoms using bis(p-nitrophenyl)phosphorazidate has been developed. Chiral tertiary alcohols were directly converted into the corresponding chiral tertiary azides with complete inversion of configuration. Several α,α-disubstituted α-amino esters or amino acids were prepared through the conversion of azides to the corresponding amines by catalytic hydrogenation.

PROCESS FOR PRODUCING SOLID AMINO ACID

The problem to be solved by the present invention is to ea lily and efficiently produce an amino acid having 2 to 7 carbon atoms as a high-purity solid without complicated operation, which is useful as a synthetic intermediate for medicines or agrochemicals. The present invention is characterized in comprising a step of precipitating solid amino acid with high purity. In the present invention, the by-produced salt composed of the sulfonic acid and the amine was removed to the mother liquor by reacting an amine with a sulfonic acid salt of amino acid in an aprotic polar solvent, or by reacting a sulfonic acid with an amine salt of amino acid in an aprotic polar solvent. The sulfonic acid salt of amino acid, for example, may be produced by reacting a N-(tert-butoxycarbonyl) amino acid with a sulfonic acid, or by reacting an amino acid tert-butyl ester with a sulfonic acid.

Synthesis and conformational analysis of efrapeptins

The efrapeptin family of peptide antibiotics produced by the fungus Tolypocladium niveum, and the neo-efrapeptins from the fungus Geotrichum candidumare inhibitors of F1-ATPase with promising antitumor, antimalaria, and insecticidal activity. They are rich in Cα- dialkyl amino acids (Aib, Iva, Acc) and contain one β-alanine and several pipecolic acid residues. The C-terminus bears an unusual heterocyclic cationic cap. The efrapeptins C-G and three analogues of efrapeptin C were synthesized using α-azido carboxylic acids as masked amino acid derivatives. All compounds display inhibitory activity toward F1-ATPase. The conformation in solution of the peptides was investigated with electronic CD spectroscopy, FT-IR spectroscopy, and VCD spectroscopy. All efrapeptins and most efrapeptin analogues were shown to adopt helical conformations in solution. In the case of efrapeptin C, VCD spectra proved that a 310-helix prevails. In addition, efrapeptin C was conformationally studied in detail with NMR and molecular modeling. Besides NOE distance restraints, residual dipolar couplings (RDC) observed upon partial alignment with stretched PDMS gels were used for the conformational analysis and confirmed the 310-helical conformation. Copyright

Asymmetric synthesis of α-methyl-α-amino acids via diastereoselective alkylation of (1s)-(+)-3-carene derived tricyclic iminolactone

A novel carene-based alanine-equivalent tricyclic iminolactone 16 has been synthesized via stereoselective dihydroxylation of the double bond, IBX oxidation of the secondary alcohol, esterification of the tertiary alcohol, deprotection of the resulting ester, and subsequent cyclization from commercially available (1S)-(+)-3-carene in 79% overall yield. The iminolactone 16 demonstrated high reactivity toward alkylation with a wide range of electrophiles at room temperature under phasetransfer catalysis conditions. The alkylated products were produced with excellent diastereoselectivities (>98% de) in good isolated yields (86-94%). High yields (83-91%) of optically pure (S)-R-methyl-R-substituted-R-amino acids were obtained by basic hydrolysis of the dialkylated iminolactones with the recovery of the chiral auxiliary 15 (78-87%).

A new type of oxidation-reduction condensation by the combined use of phenyl diphenylphosphinite and oxidant

A new type of oxidation-reduction condensation of alcohols with sulfur, nitrogen, and oxygen nucleophiles by the combined use of phenyl diphenylphosphinite (PhOPPh2) and oxidants such as azides or diethyl azodicarboxylate (DEAD) are described. In these reactions, chiral secondary and tertiary alcohols are converted into the corresponding chiral sulfides, azides, esters and ethers under mild and neutral conditions with almost complete inversion of stereochemical configuration.