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Details

Stereochemistry RACEMIC
Molecular Formula C4H7NO2
Molecular Weight 101.1039
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2-AZETIDINECARBOXYLIC ACID

SMILES

OC(=O)C1CCN1

InChI

InChIKey=IADUEWIQBXOCDZ-UHFFFAOYSA-N
InChI=1S/C4H7NO2/c6-4(7)3-1-2-5-3/h3,5H,1-2H2,(H,6,7)

HIDE SMILES / InChI

Approval Year

PubMed

PubMed

TitleDatePubMed
The application of the yeast N-acetyltransferase MPR1 gene and the proline analogue L-azetidine-2-carboxylic acid as a selectable marker system for plant transformation.
2010-06
Heterologous expression of Saccharomyces cerevisiae MPR1 gene confers tolerance to ethanol and L: -azetidine-2-carboxylic acid in Hansenula polymorpha.
2010-02
Synthesis and evaluation of new endomorphin analogues modified at the Pro(2) residue.
2009-08-01
Engineering of the yeast antioxidant enzyme Mpr1 for enhanced activity and stability.
2009-06-01
Engineering of the yeast ubiquitin ligase Rsp5: isolation of a new variant that induces constitutive inactivation of the general amino acid permease Gap1.
2009-02
Azetidine-2-carboxylic acid in the food chain.
2009-01
The discovery of BMAA, and examples of biomagnification and protein incorporation involving other non-protein amino acids.
2009
Actions of a proline analogue, L-thiazolidine-4-carboxylic acid (T4C), on Trypanosoma cruzi.
2009
Misincorporation of the proline analog azetidine-2-carboxylic acid in the pathogenesis of multiple sclerosis: a hypothesis.
2008-11
Identification of amino acid residues essential for the yeast N-acetyltransferase Mpr1 activity by site-directed mutagenesis.
2008-06
A yeast three-hybrid system that reconstitutes mammalian hypoxia inducible factor regulatory machinery.
2008-04-10
Azetidine-derived amino acids versus proline derivatives. alternative trends in reverse turn induction.
2008-03-07
Azetidine-2-carboxylic acid in garden beets (Beta vulgaris).
2006-05
The special five-membered ring of proline: An experimental and theoretical investigation of alkali metal cation interactions with proline and its four- and six-membered ring analogues.
2006-03-23
Distinct yet linked: chaperone networks in the eukaryotic cytosol.
2006
Practical asymmetric preparation of azetidine-2-carboxylic acid.
2005-10-28
Efficient route to (S)-azetidine-2-carboxylic acid.
2005-10
Substrate specificity and functional characterisation of the H+/amino acid transporter rat PAT2 (Slc36a2).
2005-01
Many amino acid substitutions in a hypoxia-inducible transcription factor (HIF)-1alpha-like peptide cause only minor changes in its hydroxylation by the HIF prolyl 4-hydroxylases: substitution of 3,4-dehydroproline or azetidine-2-carboxylic acid for the proline leads to a high rate of uncoupled 2-oxoglutarate decarboxylation.
2004-12-31
Azetidine-induced accumulation of class I small heat shock proteins in the soluble fraction provides thermotolerance in soybean seedlings.
2004-12
Protein-tyrosine phosphatase 1B potentiates IRE1 signaling during endoplasmic reticulum stress.
2004-11-26
Characterization of the genomic structures and selective expression profiles of nine class I small heat shock protein genes clustered on two chromosomes in rice (Oryza sativa L.).
2004-11
Expression of a novel yeast gene that detoxifies the proline analog azetidine-2-carboxylate confers resistance during tobacco seed germination, callus and shoot formation.
2004-03
Four permeases import proline and the toxic proline analogue azetidine-2-carboxylate into yeast.
2004-02
Characterization of novel acetyltransferases found in budding and fission yeasts that detoxify a proline analogue, azetidine-2-carboxylic acid.
2003-01
Structure-activity relationships of dynorphin analogs substituted in positions 2 and 3.
2003
Misfolded proteins are competent to mediate a subset of the responses to heat shock in Saccharomyces cerevisiae.
2002-11-22
Proline residues at the C terminus of nascent chains induce SsrA tagging during translation termination.
2002-09-13
Differential expression of two stress-inducible hsp70 genes by various stressors.
2002-05-31
A novel acetyltransferase found in Saccharomyces cerevisiae Sigma1278b that detoxifies a proline analogue, azetidine-2-carboxylic acid.
2001-11-09
Coinduction of two low-molecular-weight stress proteins, alpha B crystallin and HSP28, by heat or arsenite stress in human glioma cells.
1993-11
Name Type Language
2-AZETIDINECARBOXYLIC ACID
MI  
Systematic Name English
2-AZETIDINECARBOXYLIC ACID [MI]
Preferred Name English
DL-2-AZETIDINECARBOXYLIC ACID
Common Name English
(±)-2-AZETIDINECARBOXYLIC ACID
Systematic Name English
2-AZETIDINECARBOXYLIC ACID, (RS)-
Common Name English
2-AZETIDINECARBOXYLIC ACID, (±)-
Common Name English
Code System Code Type Description
FDA UNII
775261TI36
Created by admin on Mon Mar 31 23:05:13 GMT 2025 , Edited by admin on Mon Mar 31 23:05:13 GMT 2025
PRIMARY
EPA CompTox
DTXSID80859699
Created by admin on Mon Mar 31 23:05:13 GMT 2025 , Edited by admin on Mon Mar 31 23:05:13 GMT 2025
PRIMARY
ECHA (EC/EINECS)
219-740-2
Created by admin on Mon Mar 31 23:05:13 GMT 2025 , Edited by admin on Mon Mar 31 23:05:13 GMT 2025
PRIMARY
CAS
2517-04-6
Created by admin on Mon Mar 31 23:05:13 GMT 2025 , Edited by admin on Mon Mar 31 23:05:13 GMT 2025
PRIMARY
MERCK INDEX
m2171
Created by admin on Mon Mar 31 23:05:13 GMT 2025 , Edited by admin on Mon Mar 31 23:05:13 GMT 2025
PRIMARY Merck Index
PUBCHEM
17288
Created by admin on Mon Mar 31 23:05:13 GMT 2025 , Edited by admin on Mon Mar 31 23:05:13 GMT 2025
PRIMARY