465-58-7

Basic information

• Product Name: 2-AMINO-2-METHYLBUTYRIC ACID
• Synonyms: 2-AMINO-2-METHYL-BUTYRIC ACID, RAC;2-AMINO-2-METHYLBUTYRIC ACID;ISOVALINE
• CAS NO: 465-58-7
• Molecular Formula: C5H11NO2
• Molecular Weight: 117.15
• Product Categories: Amino Acids
• Mol File: 465-58-7.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 213.6°Cat760mmHg
• Flash Point: 83°C
• Appearance: /
• Density: 1.07g/cm³
• CAS DataBase Reference: 2-AMINO-2-METHYLBUTYRIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-2-METHYLBUTYRIC ACID(465-58-7)
• EPA Substance Registry System: 2-AMINO-2-METHYLBUTYRIC ACID(465-58-7)

Safety Data

• Hazardous Substances Data: 465-58-7(Hazardous Substances Data)

Usage

Uses

a-Me-Gly(Ethyl)-OH is used in preparation of peptide compound comprising highly sterically hindered amino acid via reaction of electron-withdrawing group-protected N-unsubstituted-α,α-disubstituted amino acid with peptide followed by N-alkylation.

Upstream product

• 59209-90-4 (RS)-2-amino-2-methylbutanamide 
• 7647-01-0 hydrogenchloride 
• 5394-36-5 5-ethyl-5-methylimidazolidine-2,4-dione 
• 54086-29-2 benzyl 2-hydroxy-2-methylbutanoate 
• 86960-59-0 N-chloroacetyl-D-isovaline 
• 2576-61-6 4-ethyl-4-methyl-2-phenyl-4H-oxazol-5-one 
• 74-96-4 ethyl bromide 
• 10065-72-2 L-Alanine methyl ester 
• 420-37-1 trimethoxonium tetrafluoroborate 
• 52812-57-4 (Z)-1-iodo-2-methyl-1-butene 
• 29588-10-1 (+/-)-2-formylamino-2-methyl-butyric acid 
• 58279-59-7 N-chloroacetyl-DL-isovaline 
• 123463-75-2 (1R,3R,4S)-8-phenyl-p-menthan-3-yl hydrogen ethyl(methyl)malonate 
• 595-39-1 DL-isovaline 

Downstream Products

• 10196-30-2 (R)-2-amino-2-methylbutan-1-ol 
• 92760-72-0 L-isovalin methyl ester hydrochloride 
• 73473-40-2 (2R)-2-amino-2-methylbutanoic acid hydrochloride 
• 123254-58-0 (R)-2-((tert-butoxycarbonyl)amino)-2-methylbutanoic acid 
• 16820-12-5 (5R)-5-ethyl-5-methylimidazolidine-2,4-dione 
• 160171-18-6 (+)-S-zoxamide 
• 118725-00-1 methyl (R)-2-amino-2-methyl-butyrate hydrochloride 
• 160171-18-6 (-)-R-zoxamide 
• 56247-82-6 α-ethylalanine ethyl ester 

Relevant articles and documents

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.

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.

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.