2133-34-8
Chemical Structure
L-Azetidine-2-carboxylic acid
- CAS No.: 2133-34-8
- Formula:C4H7NO2
- Molecular Weight:101.10
IUPAC Name: (S)-azetidine-2-carboxylic acid
InChIKey: IADUEWIQBXOCDZ-VKHMYHEASA-N
SMILES: O=C([C@H]1NCC1)O
Biological Activity: 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].
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L-Azetidine-2-carboxylic acid | 99.97% | 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. | ||||||||||||||||||||
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L-Azetidine-2-carboxylic acid (Standard) | ≥98% | 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. | ||||||||||||||||||||
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References
- [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. [Content Brief]
- [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. [Content Brief]
- [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. [Content Brief]
- [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. [Content Brief]
- [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. [Content Brief]
- [6]. Joneja MG. Teratogenic effects of proline analogue L-azetidine-2-carboxylic acid in hamster fetuses. Teratology. 1981 Jun;23(3):365-72. [Content Brief]
- [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. [Content Brief]
