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A0760

Sigma-Aldrich

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
Beilstein/REAXYS Number:
80680
EC Number:
MDL number:
UNSPSC Code:
12352209
PubChem Substance ID:
NACRES:
NA.32

assay

≥99%

form

powder

SMILES string

OC(=O)[C@@H]1CCN1

InChI

1S/C4H7NO2/c6-4(7)3-1-2-5-3/h3,5H,1-2H2,(H,6,7)/t3-/m0/s1

InChI key

IADUEWIQBXOCDZ-VKHMYHEASA-N

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General description

L-Azetidine-2-carboxylic acid is a non-protein amino acid and teratogenic agent. It is toxic in nature.

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. It is a four-membered ring analog of L-proline that causes protein misconstruction when incorporated instead of proline.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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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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
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
Azetidine-2-carboxylic acid in garden beets (Beta vulgaris)
Rubenstein E, et al.
Phytochemistry, 67(9), 898-903 (2006)
Essential function of Mec1, the budding yeast ATM/ATR checkpoint-response kinase, in protein homeostasis
Corcoles-Saez I, et al.
Developmental Cell, 46(4), 495-503 (2018)
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

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