(S)-(-)-2-azetidine carboxylic acid

azetidine-2-carboxylic acid, L-

CAS: 2133-34-8 C4 H7 N O2 MW: 101.10519000

Identification

Name(S)-(-)-2-azetidine carboxylic acid
CAS Number2133-34-8
EINECS218-362-5
FDA UNII5GZ3E0L9ZU
Molecular FormulaC4 H7 N O2
Molecular Weight101.10519000
MDL NumberMFCD00005166
Nikkaji NumberJ35.234I
Beilstein080680
XlogP3-2.90 (est)

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Soluble in water, 2.631e+005 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for (S)-(-)-2-azetidine carboxylic acid usage levels up tonot for fragrance use.
Recommendation for (S)-(-)-2-azetidine carboxylic acid flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

beet root convallaria majalis root

Synonyms

(2S)- azetidine-2-carboxylic acid L- azetidine-2-carboxylic acid azetidine-2-carboxylic acid, L- (S)-(-)-2- azetidinecarboxylic acid PubMed: Chemical-Genetic Interactions with the Proline Analog L-Azetidine-2-Carboxylic Acid in Saccharomyces cerevisiae PubMed: The ER Stress Inducer l-Azetidine-2-Carboxylic Acid Elevates the Levels of Phospho-eIF2à and of LC3-II in a Ca(2+)-Dependent Manner PubMed: Incorporation of L-azetidine-2-carboxylic acid into hemoglobin in rabbit reticulocytes in vitro PubMed: Cell death and mitochondrial dysfunction induced by the dietary non-proteinogenic amino acid L-azetidine-2-carboxylic acid (Aze) PubMed: Effect of L-azetidine 2-carboxylic acid on growth and proline metabolism in Escherichia coli PubMed: Incorporation of L-azetidine-2-carboxylic acid into hemoglobin S in sickle erythrocytes in vitro PubMed: Effect of L-azetidine-2-carboxylic acid on glycosylations of collagen in chick-embryo tendon cells PubMed: Synthesis and peptide bond orientation in tetrapeptides containing L-azetidine-2-carboxylic acid and L-proline PubMed: Stereospecificity of the enzymatic dehydrogenation in the biosynthesis of 3-ethylidene-L-azetidine-2-carboxylic acid from isoleucine by Streptomyces cacaoi PubMed: Azetidine-2-carboxylic acid contaminated dietary proline as a cause of urinary excretion of 4-amino-2-(S-cysteinyl)butyric acid in patients on oral treatment with a synthetic diet PubMed: Structural changes of hair after incorporation of the proline analogue L-azetidine-2-carboxylic acid. A model of hair disease by alteration of primary structure PubMed: Biosynthesis of the polyoxins, nucleoside peptide antibiotics: a new metabolic role for L-isoleucine as a precursor for 3-ethylidene-L-azetidine-2-carboxylic acid (polyoximic acid) PubMed: Metabolism of L-azetidine-2-carboxylic acid in the alga Cyanidium caldarium PubMed: L-ascorbic acid 2-phosphate, a phosphate derivative of L-ascorbic acid, enhances the growth of cultured rabbit keratocytes PubMed: The effect of the L-azetidine-2-carboxylic acid residue on protein conformation. III. Collagen-like poly(tripeptide)s PubMed: L-ascorbic acid 2-phosphate stimulates collagen accumulation, cell proliferation, and formation of a three-dimensional tissuelike substance by skin fibroblasts PubMed: Characterization of novel acetyltransferases found in budding and fission yeasts that detoxify a proline analogue, azetidine-2-carboxylic acid PubMed: A highly conserved mechanism for the detoxification and assimilation of the toxic phytoproduct L-azetidine-2-carboxylic acid in Aspergillus nidulans PubMed: The application of the yeast N-acetyltransferase MPR1 gene and the proline analogue L-azetidine-2-carboxylic acid as a selectable marker system for plant transformation PubMed: Heterologous expression of Saccharomyces cerevisiae MPR1 gene confers tolerance to ethanol and L: -azetidine-2-carboxylic acid in Hansenula polymorpha PubMed: Many amino acid substitutions in a hypoxia-inducible transcription factor (HIF)-1alpha-like peptide cause only minor changes in its hydroxylation by the HIF prolyl 4-hydroxylases: substitution of 3,4-dehydropro PubMed: Mutant cell lines resistant to azetidine-2-carboxylic acid: alterations in the synthesis of proline from glutamic acid PubMed: Collagen synthesis in human skin fibroblasts is stimulated by a stable form of ascorbate, 2-O-alpha-D-glucopyranosyl-L-ascorbic acid PubMed: A 9 bp cis-element in the promoters of class I small heat shock protein genes on chromosome 3 in rice mediates L-azetidine-2-carboxylic acid and heat shock responses PubMed: L-azetidine-2-carboxylic acid retards lung growth and surfactant synthesis in fetal rats PubMed: [Action of L-azetidine-2 carboxylic acid on the development of the secondary palate in the mouse] PubMed: Isolation and Identification of Two l-Azetidine-2-carboxylic Acid-Degrading Soil Microorganisms, Enterobacter agglomerans and Enterobacter amnigenus PubMed: Effects of L-azetidine-2-carboxylic acid on matrix secretion and Golgi structure in fibroblasts and osteoblasts of the mouse PubMed: The effect of the l-azetidine-2-carboxylic acid residue on protein conformation. IV. Local substitutions in the collagen triple helix PubMed: An assessment of the importance of error-prone repair and point mutations to forward mutation to L-azetidine-2-carboxylic acid resistance in Escherichia coli PubMed: 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 PubMed: The effect of the L-azetidine-2-carboxylic acid residue on protein conformation. II. Homopolymers and copolymers PubMed: [The effect of an L-proline analogue, L-azetidine-2-carboxylic acid, on the phenotypic differentiation of the somite mesenchyme of chick embryos] PubMed: Teratogenic effects of proline analogue L-azetidine-2-carboxylic acid in hamster fetuses PubMed: Properties, metabolisms, and applications of (L)-proline analogues PubMed: The effect of the proline analogue l-azetidine-2-carboxylic acid (LACA) on epidermal and dermal wound repair PubMed: A novel acetyltransferase found in Saccharomyces cerevisiae Sigma1278b that detoxifies a proline analogue, azetidine-2-carboxylic acid PubMed: Effect of L-azetidine 2-carboxilic acid on the activity of the general amino-acid permease from Saccharomyces cerevisiae var. ellipsoideus PubMed: Biosynthesis of abnormal collagens with amino acid analogues. I. Incorporation of L-azetidine-2-carboxylic acid and cis-4-fluoro-L-proline into protocollagen and collagen PubMed: [Incorporation of L-azetidine-2-carboxylic acid into collagen of the skin. Structural changes] PubMed: The crystal and molecular structure of L-azetidine-2-carboxylic acid. A naturally occurring homolog of proline PubMed: The effect of the L-azetidine-2-carboxylic acid residue on protein conformation. I. Conformations of the residue and of dipeptides PubMed: [Effects of L-azetidine-2-carboxylic acid on tooth morphogenesis and cytodifferentiation in mice] PubMed: Inhibition of liver fibrosis by 1-azetidine-2-carboxylic acid in rats treated with carbon tetrachloride PubMed: Inhibition of Distinct Proline- or N-Acetylglucosamine-Induced Hyphal Formation Pathways by Proline Analogs in Candida albicans PubMed: Asymmetric synthesis of L-azetidine-2-carboxylic acid and 3-substituted congeners--conformationally constrained analogs of phenylalanine, naphthylalanine, and leucine PubMed: Biosynthesis of abnormal collagens with amino acid analogues. II. Inability of cartilage cells to extrude collagen polypeptides containing L-azetidine-2-carboxylic acid or cis-4-fluoro-L-proline PubMed: Development of mouse limb buds in organ culture: chondrogenesis in the presence of a proline analog, L-azetidine-2-carboxylic acid PubMed: Corneal development. IV. Interruption of collagen excretion into the primary stroma of the cornea with L-azetidine-2-carboxylic acid PubMed: Regio- and stereoselective oxygenation of proline derivatives by using microbial 2-oxoglutarate-dependent dioxygenases PubMed: [Effect of an analog of proline (L-azetidine-2-carboxylic acid) on in vitro differentiation of the rat fetal testis] PubMed: The proline analog L-azetidine-2-carboxylic acid modifies the neovascularization pattern by inhibiting branching or tortuosity and stimulating spatial expansion in the rat mesentery PubMed: Transport of pharmacologically active proline derivatives by the human proton-coupled amino acid transporter hPAT1 PubMed: Proline uptake in Candida albicans PubMed: The Unfolded Protein Response PubMed: Role of ascorbic acid in the regulation of proliferation in osteoblast-like MC3T3-E1 cells PubMed: Incorporation of L-azetidine-2-carboxylic acid into hemoglobin in rabbit reticulocytes PubMed: Substrate specificity of the amino acid transporter PAT1 PubMed: Effects of l-azetidine-2-carboxylic acid, a proline analogue, on the in vitro development of mouse tooth germs PubMed: Involvement of the stress-responsive transcription factor gene MSN2 in the control of amino acid uptake in Saccharomyces cerevisiae PubMed: Biochemical characterization of azetidine carboxylic acid-resistant Chinese hamster cells PubMed: Amnestic potency of proline analogs correlates with anti-spreading depression potency PubMed: The effects of L-azetidine-2-carboxylic acid (analogue of proline) on dental cytodifferentiations in vitro PubMed: The sodium/proline transporter PutP of Helicobacter pylori PubMed: Comparative radioautographic study of the effects of L-azetidine-2-carboxylic acid on matrix secretion and Golgi of the mouse incisor PubMed: L-Proline and related compounds: correlation of structure, amnesic potency and anti-spreading depression potency PubMed: L-Proline transport in Saccharomyces cerevisiae PubMed: Variant Chinese hamster cells resistant to the proline analog L-azetidine 2-carboxylic acid PubMed: Effect of the administration of L-azetidine-2-carboxylic acid on albumin and transferrin biosynthesis by liver slices of rats treated with carbon tetrachloride PubMed: Two potentially angiostatic factors, a steroid and L-azetidine-2-carboxylic acid, antagonize one another PubMed: Ascorbic acid stimulates barrier function of cultured endothelial cell monolayer PubMed: Saccharomyces cerevisiae sigma 1278b has novel genes of the N-acetyltransferase gene superfamily required for L-proline analogue resistance PubMed: Growth inhibition of japanese encephalitis virus by l-azetidine-2-carboxylic acid PubMed: s-Cis...and s-trans isomerism in acylproline analogs. Models for conformationally locked proline peptides PubMed: Influence of a proton gradient on the transport kinetics of the H+/amino acid cotransporter PAT1 in Caco-2 cells PubMed: The Aspergillus nidulans proline permease as a model for understanding the factors determining substrate binding and specificity of fungal amino acid transporters PubMed: Conformational preferences of proline analogues with different ring size PubMed: Polymorphism of the MPR1 gene required for toxic proline analogue resistance in the Saccharomyces cerevisiae complex species PubMed: Metabolic inhibitors and intermediate filament organization in human fibroblasts PubMed: MPR1 as a novel selection marker in Saccharomyces cerevisiae PubMed: Proline analogues inhibit human skin fibroblast growth and collagen production in culture PubMed: A nonconserved Ala401 in the yeast Rsp5 ubiquitin ligase is involved in degradation of Gap1 permease and stress-induced abnormal proteins PubMed: Crystallization and preliminary crystallographic analysis of N-acetyltransferase Mpr1 from Saccharomyces cerevisiae PubMed: Novel function of ascorbic acid as an angiostatic factor PubMed: Hydroxyproline in the major capsid protein VP1 of polyomavirus PubMed: Antimutagenic unusual amino acids from plants PubMed: The THERMOSENSITIVE MALE STERILE 1 Interacts with the BiPs via DnaJ Domain and Stimulates Their ATPase Enzyme Activities in Arabidopsis PubMed: Effects of L-proline and some of its analogs on retinal spreading of depression PubMed: Hsp70-GlcNAc-binding activity is released by stress, proteasome inhibition, and protein misfolding PubMed: Calnexin phosphorylation attenuates the release of partially misfolded alpha1-antitrypsin to the secretory pathway PubMed: Up-regulation of the clusterin gene after proteotoxic stress: implication of HSF1-HSF2 heterocomplexes PubMed: Mutagenicity of antibiotics in microbial assays. Problems of evaluation PubMed: Precardiac mesoderm differentiation in vitro. Actin-isotype synthetic transitions, myofibrillogenesis, initiation of heartbeat, and the possible involvement of collagen PubMed: Heterogeneity in ornithine cytotoxicity of bovine retinal pigment epithelial cells in primary culture PubMed: An experimental analysis of somite segmentation in the chick embryo PubMed: Cellular and biochemical events in mammalian cells during and after recovery from physiological stress PubMed: Effects of antifibrotic substances on pancreatic fibrosis following acute necrotizing pancreatitis PubMed: The sarco/endoplasmic reticulum calcium-ATPase 2b is an endoplasmic reticulum stress-inducible protein PubMed: Mutations in the listerial proB gene leading to proline overproduction: effects on salt tolerance and murine infection PubMed: Induction of novel Grp75 isoforms by 2-deoxyglucose in human and murine fibroblasts PubMed: Smad3 promotes alkaline phosphatase activity and mineralization of osteoblastic MC3T3-E1 cells PubMed: Ascorbate affects proliferation of guinea-pig vascular smooth muscle cells by direct and extracellular matrix-mediated effects PubMed: Effects of ring contraction on the conformational preferences of à-substituted proline analogs PubMed: Involvement of collagen formation in the hormonally induced functional differentiation of mouse mammary gland in organ culture PubMed: Two collagen-binding proteins, osteonectin and HSP47, are coordinately induced in transformed keratinocytes by heat and other stresses PubMed: Collagen-production inhibitors evaluated as antitumor agents PubMed: Methylation of atypical protein aspartyl residues during the stress response of HeLa cells PubMed: Liver collagen synthesis in murine schistosomiasis PubMed: Effect of colchicine on collagen, albumin and transferrin synthesis by cirrhotic rat liver slices PubMed: Enhanced phosphorylation of a 65 kDa protein is associated with rapid induction of stress proteins in 9L rat brain tumor cells PubMed: Role of the pyrrolidine ring of proline in determining the substrate specificity of cdc2 kinase or cdk5 PubMed: Upregulation of cytosolic chaperonin CCT subunits during recovery from chemical stress that causes accumulation of unfolded proteins PubMed: Activation of heat shock gene transcription by heat shock factor 1 involves oligomerization, acquisition of DNA-binding activity, and nuclear localization and can occur in the absence of stress PubMed: Inhibition of tumor-cell attachment to extracellular matrix as a method for preventing tumor recurrence in a surgical wound PubMed: Synthesis of collagen: chemical regulation of post-translational events PubMed: Suppression of thermotolerance development through cycloheximide-induced negative control of stress protein gene expression PubMed: 70 kDa heat shock cognate protein is a transformation-associated antigen and a possible target for the host's anti-tumor immunity PubMed: Effect of novel compound, 1-methyl-1-piperidino methane sulfonate (MPMS), on the osmoprotectant activity of glycine betaine, choline and L-proline in Escherichia coli PubMed: Characterization of the thermotolerant cell. I. Effects on protein synthesis activity and the regulation of heat-shock protein 70 expression PubMed: Expression of a novel yeast gene that detoxifies the proline analog azetidine-2-carboxylate confers resistance during tobacco seed germination, callus and shoot formation PubMed: Effect of proline analogs on oxygen toxicity-induced pulmonary fibrosis in the rat PubMed: Differential expression of two stress-inducible hsp70 genes by various stressors PubMed: Implication of a small GTPase Rac1 in the activation of c-Jun N-terminal kinase and heat shock factor in response to heat shock PubMed: Interference with thyroid histogenesis by inhibitors of collagen synthesis PubMed: Fine structure of extracellular matrix and basal laminae in two types of abnormal collagen production: L-proline analog-treated otocyst cultures and disproportionate micromelia (Dmm/Dmm) mutants PubMed: Introduction of Pro and its analogues in the conserved P1' position of trypsin inhibitor SFTI-1 retains its inhibitory activity PubMed: Induction of 32- and 34-kDa stress proteins by sodium arsenite, heavy metals, and thiol-reactive agents PubMed: [Transfer of bacterial genes for proline synthesis in plants and their expression by various plant promotors] PubMed: Effects of glycoprotein and basement membrane synthesis inhibitors on the growth of cultured renal collecting duct epithelium PubMed: Proteasome inhibition enhances resistance to DNA damage via upregulation of Rpn4-dependent DNA repair genes PubMed: Extracellular matrix synthesis is required for the movement of sclerotome and neural crest cells on collagen PubMed: Prolyl hydroxylase inhibitor and lysyl hydroxylase inhibitor inhibit spreading of corneal epithelium PubMed: Basal lamina inhibition suppresses synthesis of calcium-dependent proteins associated with mammary epithelial cell spreading PubMed: Expression of heat stress proteins by human periodontal ligament cells PubMed: Contribution of heat shock proteins to cell protection from complement-mediated lysis PubMed: Evidence for positive regulation of the proline utilization pathway in Saccharomyces cerevisiae PubMed: Amino acid analogs while inducing heat shock proteins sensitize CHO cells to thermal damage PubMed: Induced structural defects in T-even bacteriophage PubMed: The proton affinity of proline analogs using the kinetic method with full entropy analysis PubMed: Selection and characterization of chlorella mutants deficient in amino Acid transport : further evidence for three independent systems PubMed: Synthesis and biological activities of angiotensin II, Sarilesin, and Sarmesin analogues containing Aze or Pip at position 7 PubMed: Induction of the 72-kD heat shock protein in organ-cultured normal human skin PubMed: Role of glycosaminoglycans and collagen in the development of a fibronectin-rich extracellular matrix in cultured embryonic corneal epithelial cells PubMed: Collagen type II in the otic extracellular matrix. Effect on inner ear development PubMed: Analysis of intracellular feline leukemia virus proteins II. Generation of feline leukemia virus structural proteins from precursor polypeptides PubMed: Changes in k, rb, and na transport to shoots after anoxia PubMed: In vitro utilization of exogenous procollagen by embryonic tooth germs PubMed: Collagen metabolism and spicule formation in sea urchin micromeres PubMed: Proline accumulation in a barley mutant resistant to trans-4-hydroxy-L-proline PubMed: Isolation and characterisation of a cDNA encoding rat mitochondrial GrpE, a stress-inducible nucleotide-exchange factor of ubiquitous appearance in mammalian organs PubMed: Nitrogen Enhancement of Phosphate Transport in Roots of Zea mays L: II. Kinetic and Inhibitor Studies PubMed: Cotransport of proline and Li+ in Escherichia coli PubMed: Experimental control of the differentiation of Leydig cells in the rat fetal testis PubMed: Biochemical and ultrastructural study of the effects of proline analogues on collagen synthesis in 3T6 fibroblasts PubMed: Dysmorphogenesis of the inner ear: disruption of extracellular matrix (ECM) formation by an L-proline analog in otic explants PubMed: Pharmacological inhibition of excessive collagen deposition in fibrotic diseases PubMed: Age-dependent disruption of basal lamina and extracellular matrix formation in L-proline analog treated otic explants