L-Azetidine-2-carboxylic acid

L-Azetidine-2-carboxylic acid is a proline analog. L-Azetidine-2-carboxylic acid upregulates the lipid autophagy marker LC3-II via activation of the PERK pathway. L-Azetidine-2-carboxylic acid increases pro-apoptotic BAX protein. L-Azetidine-2-carboxylic acid induces ATF6 cleavage and upregulates phosphorylated eIF2α levels. L-Azetidine-2-carboxylic acid induces ER stress, inducing protein misfolding and aggregation. L-Azetidine-2-carboxylic acid shows teratogenic, pro-inflammatory and pro-apoptotic effects[1][2][3][4][5][6][7][8][9].

Product Specifications

CAS Number

[2133-34-8]

UNSPSC

12352005

Hazard Statement

H302, H315, H319, H335

Target

Apoptosis; ATF6; Atg8/LC3; Autophagy; Bcl-2 Family; Endogenous Metabolite; Eukaryotic Initiation Factor (eIF) ; PERK

Type

Natural Products

Related Pathways

Apoptosis; Autophagy; Cell Cycle/DNA Damage; Metabolic Enzyme/Protease

Applications

Metabolism-sugar/lipid metabolism

Field of Research

Cancer; Endocrinology; Metabolic Disease; Neurological Disease; Cardiovascular Disease

Assay Protocol

https://www.medchemexpress.com/l-azetidine-2-carboxylic-acid.html

Purity

99.85

Solubility

DMSO : < 1 mg/mL (ultrasonic) |H2O : 100 mg/mL (ultrasonic)

Smiles

O=C([C@H]1NCC1)O

Molecular Formula

C4H7NO2

Molecular Weight

101.10

Precautions

H302, H315, H319, H335

References & Citations

[1]Oikarinen A, et al. Effect of L-azetidine-2-carboxylic acid on glycosylations of collagen in chick-embryo tendon cells. Biochem J. 1976 Dec 15;160 (3) :639-45.|[2]Roest G, et al. The ER Stress Inducer l-Azetidine-2-Carboxylic Acid Elevates the Levels of Phospho-eIF2α and of LC3-II in a Ca2+-Dependent Manner. Cells. 2018 Nov 30;7 (12) :239.|[3]Baum BJ, et al. Incorporation of L-azetidine-2-carboxylic acid into hemoglobin in rabbit reticulocytes in vitro. J Biol Chem. 1975 Feb 25;250 (4) :1464-71.|[4]Hall BK. Use of the L-proline analog, L-azetidine-2-carboxylic acid (LACA) to analyse embryonic growth and determination and expression of the chondrogenic phenotype in vivo and in vitro. Anat Rec. 1978 Feb;190 (2) :243-55.|[5]Piper JA, et al. Pro-Inflammatory and Pro-Apoptotic Effects of the Non-Protein Amino Acid L-Azetidine-2-Carboxylic Acid in BV2 Microglial Cells. Curr Issues Mol Biol. 2022 Sep 28;44 (10) :4500-4516.|[6]Joneja MG. Teratogenic effects of proline analogue L-azetidine-2-carboxylic acid in hamster fetuses. Teratology. 1981 Jun;23 (3) :365-72.|[7]NAGAI H, et al. Teratogenic Effect of Proline Analogue L-azetidine-2-carboxylic acid on the Skeletal System in Rats. official journal of Congeital Anomalies Research Association of Japan, 1978, 18 (1) : 19-23.|[8]NAGAI H, et al. Disturbance of Dentine Formation in Rats and Mice after Administration of L-azetidine-2-carboxylic acid. official journal of Congeital Anomalies Research Association of Japan, 1978, 18 (1) : 25-31.|[9]Adamson IY, et al. L-azetidine-2-carboxylic acid retards lung growth and surfactant synthesis in fetal rats. Lab Invest.