.ALPHA.-AMINOISOBUTYRIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C4H9NO2
Molecular Weight	103.1198
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of .ALPHA.-AMINOISOBUTYRIC ACID

Structure Search

SMILES

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

InChI

InChIKey=FUOOLUPWFVMBKG-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C4H9NO2
Molecular Weight	103.1198
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Effects of acute hyperosmolality on blood-brain barrier function in ovine fetuses and lambs.	2006-10	16690764
Effects of multiple courses of antenatal corticosteroids on blood-brain barrier permeability in the ovine fetus.	2006-05	16697940
In vitro and in vivo effect of parathyroid hormone analogue (1-14) containing -amino-iso-butyric acid residue (Aib)1,3.	2006-04-30	16642551
[Synergistic effects of biotic and abiotic elicitors on the production of tanshinones in Salvia miltiorrhiza hairy root culture].	2006-02	16572993
Gold nanoclusters protected by conformationally constrained peptides.	2006-01-11	16390162
Effects of VEGF and nitric oxide synthase inhibition on blood-brain barrier disruption in the ischemic and non-ischemic cerebral cortex.	2005-12	16354548
Pharmacological actions of Cordyceps, a prized folk medicine.	2005-12	16354395
Improved solid-phase synthesis of alpha,alpha-dialkylated amino acid-rich peptides with antimicrobial activity.	2005-12	16316449
Analysis of the lipophilic peptaibol alamethicin by nonaqueous capillary electrophoresis-electrospray ionization-mass spectrometry.	2005-11	16287177
Theoretical prediction of gas-phase infrared spectra of imidazo[1,2-a]pyrazinediones and imidazo[1,2-a]imidazo[1,2-d]pyrazinediones derived from glycine.	2005-09	16043049
Acceleration of short helical peptide conformational dynamics by trifluoroethanol in an organic solvent.	2005-07	15937985
Helix-helix interconversion rates of short 13C-labeled helical peptides as measured by dynamic NMR spectroscopy.	2005-06-05	15657893
Effects of tumor necrosis factor-alpha on insulin stimulated amino acid transport in cultured rat hepatocytes.	2005-06	16117322
Fungal biosynthesis of non-ribosomal peptide antibiotics and alpha, alpha-dialkylated amino acid constituents.	2005-06	15635654
Preferred conformations of peptides containing tert-leucine, a sterically demanding, lipophilic alpha-amino acid with a quaternary side-chain Cbeta atom.	2005-04-08	15669065
Effects of 17beta-estradiol on blood-brain barrier disruption in focal ischemia during GABA(A) receptor inhibition.	2005-04	15952079
Chromium(V) peptide complexes: synthesis and spectroscopic characterization.	2005-02-21	15859285
Beta-turn mimic in tripeptide with Phe(1)-Aib(2) as corner residues and beta-strand structure in an isomeric tripeptide: an X-ray diffraction study.	2005-02-21	15703804
A new 2 methylalanine-PVC ESR dosimeter.	2005-02	15607463
Evidence against the hopping mechanism as an important electron transfer pathway for conformationally constrained oligopeptides.	2005-01-19	15643851
Bioactive N-terminal undecapeptides derived from parathyroid hormone: the role of alpha-helicity.	2005-01	15686531
Cicadapeptins I and II: new Aib-containing peptides from the entomopathogenic fungus Cordyceps heteropoda.	2005-01	15679316
Amino-terminal parathyroid hormone fragment analogs containing alpha,alpha-di-alkyl amino acids at positions 1 and 3.	2004-12	15537452
Ethylene synthesis and auxin augmentation in pistil tissues are important for egg cell differentiation after pollination in maize.	2004-10	15564523
Inhibition of amyloid fibril formation by peptide analogues modified with alpha-aminoisobutyric acid.	2004-08-06	15300690
Synthesis and characterization of a series of homooligopeptide peroxyesters.	2004-08-05	15281761
Conformational switching caused by biphenyl substitution at the Calpha position: ethyl 2-benzyl-2-(formylamino)-3-phenylpropionate and ethyl 3-(1,1'-biphenyl-4-yl)-2-(formylamino)-2-(4-phenylbenzyl)propionate.	2004-07	15237187
Functional and structural characteristics of NY-ESO-1-related HLA A2-restricted epitopes and the design of a novel immunogenic analogue.	2004-05-28	15004033
A novel 11-residual peptaibol-derived carrier peptide for in vitro oligodeoxynucleotide delivery into cell.	2004-05-17	15109652
Linkage of interactions in sickle hemoglobin fiber assembly: inhibitory effect emanating from mutations in the AB region of the alpha-chain is annulled by a mutation at its EF corner.	2004-05-07	14982923
Transcellular transport of radioiodinated 3-iodo-alpha-methyl-L-tyrosine across monolayers of kidney epithelial cell line LLC-PK1.	2004-05	15233284
Analysis of peptaibol sequence composition: implications for in vivo synthesis and channel formation.	2004-05	14534753
Metal ion-binding ability of tetrapeptides containing alpha-aminoisobutyric acid.	2004-03	15113087
New tools for the control of peptide conformation: the helicogenic Calpha-methyl, Calpha-cyclohexylglycine.	2004-02	15009538
Conformational changes in alamethicin associated with substitution of its alpha-methylalanines with leucines: a FTIR spectroscopic analysis and correlation with channel kinetics.	2004-01	14695266
Biosynthetic uniform 13C,15N-labelling of zervamicin IIB. Complete 13C and 15N NMR assignment.	2003-12-09	14658801
Trichogin: a paradigm for lipopeptaibols.	2003-12-09	14658789
Designed helical peptides inhibit an intramembrane protease.	2003-10-01	14505382
Effect of alpha,alpha-dialkyl amino acids on the protease resistance of peptides.	2003-10	14586119
Crystal structure of achiral nonapeptide Boc-(Aib-DeltaZPhe)4-Aib-OMe at atomic resolution: evidence for a 3(10)-helix.	2003-10	14579304
Sequence analysis and functional characterization of the dialkylglycine decarboxylase gene DGD1 from Mycosphaerella graminicola.	2003-08	12743737
Disruption of the beta-sheet structure of a protected pentapeptide, related to the beta-amyloid sequence 17-21, induced by a single, helicogenic C(alpha)-tetrasubstituted alpha-amino acid.	2003-07	12916643
Unique antitumour effects of L-2,4 diaminobutyric acid on cultured hepatoma cells.	2003-06-25	12820378
First crystallographic signature of an acyclic peptide nanorod: molecular mechanism of nanorod formation by a self-assembled tetrapeptide.	2003-06-21	12841264
Prevention of peptide fibril formation in an aqueous environment by mutation of a single residue to Aib.	2003-04-22	12693945
Functional and molecular characteristics of system L in human breast cancer cells.	2003-04-01	12659948
The effect of the cyclopropyl group on the conformation of chemotactic formyl tripeptides.	2003-04	12729567
Solution phase synthesis of the 14-residue peptaibol antibiotic trichovirin I.	2003-04	12707814
Ethyl 2-formamido-2-(4-iodobenzyl)-3-(4-iodophenyl)propionate and ethyl 2-(3-bromobenzyl)-3-(3-bromophenyl)-2-formamidopropionate.	2003-04	12682414
A MAPK pathway mediates ethylene signaling in plants.	2003-03-17	12628921

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:35:44 GMT 2025` Edited by `admin` on `Mon Mar 31 17:35:44 GMT 2025`
Record UNII	1E7ZW41IQU
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

.ALPHA.-AMINOISOBUTYRIC ACID

Systematic Name

English

NSC-16590

Preferred Name

English

2-METHYLALANINE

Systematic Name

English

.ALPHA.-AMINOISOBUTYRIC ACID [MI]

Common Name

English

AIB

Common Name

English

ALPHA-AMINOISOBUTYRIC ACID

Systematic Name

English

?-methyl-L-alanine

Common Name

English

2-AMINOISOBUTYRIC ACID

Systematic Name

English

2-AMINO-2-METHYLPROPANOIC ACID

Systematic Name

English

Code System Code Type Description

CHEBI

40599