A0760
L-Azetidine-2-carboxylic acid
≥99%
Synonym(s):
(S)-Azetidine-2-carboxylic acid
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About This Item
Empirical Formula (Hill Notation):
C4H7NO2
CAS Number:
Molecular Weight:
101.10
UNSPSC Code:
12352209
NACRES:
NA.32
PubChem Substance ID:
EC Number:
218-362-5
Beilstein/REAXYS Number:
80680
MDL number:
Product Name
L-Azetidine-2-carboxylic acid, ≥99%
InChI
1S/C4H7NO2/c6-4(7)3-1-2-5-3/h3,5H,1-2H2,(H,6,7)/t3-/m0/s1
SMILES string
OC(=O)[C@@H]1CCN1
InChI key
IADUEWIQBXOCDZ-VKHMYHEASA-N
assay
≥99%
form
powder
Quality Level
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Application
L-Azetidine-2-carboxylic acid has been used as a:
- collagen synthesis inhibitor
- protein folding antagonist
- as a standard in liquid chromatography-mass spectrometry
Biochem/physiol Actions
Azetidine-2-carboxylic acid (AZC) triggers protein aggregation or upregulates the expression of an aggregation-prone mutant protein, upon interference with nascent protein folding.
L-Azetidine-2-carboxylic acid is an inhibitor of collagen synthesis that is anti-angiogenic.
L-Azetidine-2-carboxylic acid is an inhibitor of collagen synthesis that is anti-angiogenic. It is a four-membered ring analog of L-proline that causes protein misconstruction when incorporated instead of proline.
General description
L-Azetidine-2-carboxylic acid is a non-protein amino acid and teratogenic agent. It is toxic in nature.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Kate Samardzic et al.
Amino acids, 51(8), 1221-1232 (2019-07-16)
In addition to the 20 protein amino acids that are vital to human health, hundreds of naturally occurring amino acids, known as non-proteinogenic amino acids (NPAAs), exist and can enter the human food chain. Some NPAAs are toxic through their
Asmita Ghosh et al.
Cellular and molecular life sciences : CMLS, 76(8), 1605-1621 (2019-01-27)
The proteostasis network (PN) comprises a plethora of proteins that are dedicated to aid in protein folding and maintenance; some with overlapping functions. Despite this, there are multiple pathophysiological states associated with depletion of chaperones. This is counter-intuitive, assuming cells
Azetidine-2-carboxylic acid in garden beets (Beta vulgaris)
Rubenstein E, et al.
Phytochemistry, 67(9), 898-903 (2006)
Nadinath B Nillegoda et al.
Molecular biology of the cell, 21(13), 2102-2116 (2010-05-14)
Quality control systems facilitate polypeptide folding and degradation to maintain protein homeostasis. Molecular chaperones promote folding, whereas the ubiquitin/proteasome system mediates degradation. We show here that Saccharomyces cerevisiae Ubr1 and Ubr2 ubiquitin ligases promote degradation of unfolded or misfolded cytosolic
The anticancer drug AUY922 generates a proteomics fingerprint that is highly conserved among structurally diverse Hsp90 inhibitors
Voruganti S, et al.
Journal of Proteome Research, 12(8), 3697-3706 (2013)
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