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

Supplier Sponsors

CAS Number: 2133-34-8Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:218-362-5
FDA UNII: 5GZ3E0L9ZU
Nikkaji Web:J35.234I
Beilstein Number:080680
MDL:MFCD00005166
XlogP3:-2.90 (est)
Molecular Weight:101.10519000
Formula:C4 H7 N O2
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in:
 water, 2.631e+005 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
(S)-(-)-Azetidine-2-carboxylic acid >95%
Santa Cruz Biotechnology
For experimental / research use only.
L-Azetidine Carboxylic Acid ≥98%
Sigma-Aldrich: Sigma
For experimental / research use only.
L-Azetidine Carboxylic Acid ≥99%
TCI AMERICA
For experimental / research use only.
L-Azetidine-2-carboxylic Acid [Antagonist of L-Proline] >98.0%(T)
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for (S)-(-)-2-azetidine carboxylic acid usage levels up to:
 not for fragrance use.
 
Recommendation for (S)-(-)-2-azetidine carboxylic acid flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :16486
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(2S)-azetidine-2-carboxylic acid
Chemidplus:0002133348
RTECS:CM4310500 for cas# 2133-34-8
 
References:
 (2S)-azetidine-2-carboxylic acid
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):16486
Pubchem (cas):2133-34-8
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEBI:View
CHEMBL:View
KEGG (GenomeNet):C08267
HMDB (The Human Metabolome Database):HMDB29615
FooDB:FDB000783
Export Tariff Code:2922.49.4950
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 beet root
Search Trop Picture
 convallaria majalis root
Search Trop Picture
 
Synonyms:
(2S)-azetidine-2-carboxylic acid
L-azetidine-2-carboxylic acid
 azetidine-2-carboxylic acid, L-
(S)-(-)-2-azetidinecarboxylic acid
 

Articles:

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
 
Notes:
Present in roots and leaves of Convallaria majalis (lily-of-the-valley). Convallaria majalis is banned by the FDA from food use in the USA
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