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850993

Sigma-Aldrich

2-Aminoisobutyric acid

98%, for peptide synthesis

Synonym(s):

α-Aminoisobutyric acid, 2-Methylalanine, Aib

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About This Item

Linear Formula:
(CH3)2C(NH2)COOH
CAS Number:
62-57-7
Molecular Weight:
103.12
Beilstein:
506496
EC Number:
200-544-0
MDL number:
MFCD00008049
UNSPSC Code:
12352106
PubChem Substance ID:
24888304
NACRES:
NA.22

product name

2-Aminoisobutyric acid, 98%

Assay

98%

form

solid

reaction suitability

reaction type: solution phase peptide synthesis

mp

≥300 °C

application(s)

peptide synthesis

SMILES string

CC(C)(N)C(O)=O

InChI

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

InChI key

FUOOLUPWFVMBKG-UHFFFAOYSA-N

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General description

2-Aminoisobutyric acid also known as α-aminobutyric acid, is an amino acid used in solution-phase peptide synthesis. It is a desirable building block for peptides because of its strong tendency to cause the peptide to form a helical shape.

Application

2-Aminoisobutyric acid can be used to synthesize self-assembled polypeptide nanoparticles. Incorporation of this compound into the peptide chain can prevent undesired reactions since it is di-α-substituted, and inert to C−H abstraction.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

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Photochemical methods for peptide macrocyclisation
Chemistry?A European Journal , 27, 69-88 (2021)
Amphiphilic polypeptides with prolonged enzymatic stability for the preparation of self-assembled nanobiomaterials
Royal Society of Chemistry Advances, 8, 34603-34613 (2018)
C Lucarelli et al.
Journal of chromatography, 541(1-2), 285-296 (1991-03-22)
A procedure is described for the determination of alpha-methyldopa (MD) [L-3-(3,4-dihydroxyphenyl)-2-methylalanine], its metabolite and catecholamines in the urine and plasma of patients undergoing MD therapy, by high-performance liquid chromatography with dual working electrode coulometric detection. An efficient sample preparation procedure
Øyvind Jacobsen et al.
The Journal of organic chemistry, 76(5), 1228-1238 (2011-02-01)
Short peptides are important as lead compounds and molecular probes in drug discovery and chemical biology, but their well-known drawbacks, such as high conformational flexibility, protease lability, poor bioavailability and short half-lives in vivo, have prevented their potential from being
Jamie E Elsila et al.
Astrobiology, 11(2), 123-133 (2011-03-23)
The presence of nonprotein α-dialkyl-amino acids such as α-aminoisobutyric acid (α-AIB) and isovaline (Iva), which are considered to be relatively rare in the terrestrial biosphere, has long been used as an indication of the indigeneity of meteoritic amino acids. However
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