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Key Documents

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

Quality Level

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 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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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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