2133-34-8O=C(O)[C@@H]1CCN1IADUEWIQBXOCDZ-VKHMYHEASA-N(S)-azetidine-2-carboxylic acid is the (S)-enantiomer of azetidine-2-carboxylic acid. It is an enantiomer of a (R)-azetidine-2-carboxylic acid. It is a tautomer of a (S)-azetidine-2-carboxylate zwitterion.
2133-34-8Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.
Warning
H315 (66.7%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
THE CHRONIC ADMINISTRATION OF CARBON TETRACHLORIDE TO RATS INDUCED CIRRHOSIS AND INCREASED ALBUMIN SYNTHESIS, BUT SIMULTANEOUS ADMIN OF CARBON TETRACHLORIDE WITH L-AZETIDINE-2-CARBOXYLIC ACID DECR ALBUMIN SYNTHESIS AND ELICITED A RETURN OF SERUM ALBUMIN LEVELS TO NORMAL VALUES.
L-AZETIDINE-2-CARBOXYLIC ACID SEVERELY INHIBITED THE INDUCTION OF NITRATE REDUCTASE BY NITRATE IN RADISH AND CAULIFLOWER LEAF TISSUES WITH A LOW L-PROLINE CONTENT. INHIBITION WAS REVERSED BY SIMULTANEOUS INFILTRATION OF L-PROLINE.
ALLYLGLYCINE (0.1 MMOL) INHIBITED THE UPTAKE OF 0.1 UMOL 4,5-(3)H-LABELED L-LEUCINE (1 CURIE/MMOLE) AND U-(3)H-LABELED L-PROLINE (266 MCI/MMOLE) BY RAT BRAIN SLICES. LEUCINE UPTAKE WAS NOT LINEAR WITH TIME; PROLINE UPTAKE WAS ALSO INHIBITED BY L-AZETIDINE-2-CARBOXYLIC ACID.
L-AZETIDINE-2-CARBOXYLIC ACID WAS POTENT IN CAUSING AMNESIA OF 1-TRIAL AVOIDANCE CONDITIONING OF THE 2-DAY-OLD CHICK AND IN PREVENTING MECHANICALLY INDUCED SPREADING DEPRESSION IN THE RETINA ISOLATED FROM 2-3 WK-OLD CHICKS. L-AZETIDINE-2-CARBOXYLIC ACID IS INCORPORATED INTO PROTEIN IN PLACE OF L-PROLINE IN SEVERAL PROTEIN-SYNTHESIZING SYSTEMS.
THE ADDITION OF L-AZETIDINE-2-CARBOXYLIC ACID TO THE INCUBATION MEDIUM OF FETAL RAT CALVARIA DECREASED THE INTRACELLULAR FREE PROLINE AND THE RATES OF PROLINE INCORPORATION INTO PROTEIN AND COLLAGEN BY 40-70%. THE ALTERATIONS IN INTRACELLULAR PROLINE CONCN PRODUCED EITHER BY VARYING EXTRACELLULAR PROLINE CONCN OR BY INHIBITING THE UPTAKE OF PROLINE INTO THE INTRACELLULAR POOL MAY CONTRIBUTE TO THE REGULATION OF COLLAGEN SYNTHESIS.
PROLINE PERMEASE FROM PSEUDOMONAS AERUGINOSA OBEYED SATURATION KINETICS & WAS SPECIFIC FOR L-PROLINE. L-AZETIDINE-2-CARBOXYLIC ACID COMPETITIVELY INHIBITED PROLINE UPTAKE. IT WAS ALSO ABLE TO EXCHANGE WITH A PRE-ESTABLISHED LABELED PROLINE INTRACELLULAR POOL.
SIXTEEN-DAY-OLD MOUSE EMBRYONIC ODONTOBLASTS, TREATED FOR 4 DAYS WITH L-2-AZETIDINECARBOXYLIC ACID (50, 100, & 200 GAMMA) WERE POST-MITOTIC, BUT NONPOLARIZED AND DID NOT SECRETE PICROFUCHSIN-POSITIVE SUBSTANCES (COLLAGEN). 18-DAY-OLD EMBRYONIC ODONTOBLASTS TREATED WITH L-2-AZETIDINECARBOXYLIC CONTAINED NO PICROFUCHSIN-POSITIVE SUBSTANCES AND NO COLLAGEN FIBERS OF STRIATION; PREADAMANTOBLASTS WERE POST-MITOTIC BUT NONPOLARIZED.
2-Azetidinecarboxylic acid: Found in the flowering Lily-of-the-valley and Solomon's seal; Has growth-inhibitory activity on E. coli cultures and germinating seeds; Also a proline analog that produces abnormal proteins with impaired biological activity; [Merck Index]
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DTXSID0044020CHEMBL1165239CHEBI:6198INCUBATION OF HUMAN SKIN FIBROBLASTS IN CULTURE WITH L-AZETIDINE-2-CARBOXYLIC ACID (LACA) REDUCED THE RATE OF FIBROBLAST PROLIFERATION AND LOWERED THE PLATING EFFICIENCY. FIBROBLASTS SYNTHESIZED PROCOLLAGEN POLYPEPTIDES WHICH WERE NOT IN A TRIPLE-HELICAL CONFORMATION. THE PROLINE ANALOGS THUS APPEAR TO INHIBIT THE PRODUCTION OF PROCOLLAGEN ON THE POST-TRANSLATIONAL LEVEL BY PREVENTING THE POLYPEPTIDES FROM FOLDING INTO A STABLE TRIPLE-HELICAL CONFORMATION. INHIBITION OF PROCOLLAGEN WAS NOTED IN SCLERODERMA CELLS AS WITH CONTROL FIBROBLAST CULTURES. PROLINE ANALOGS MAY BE USEFUL IN LIMITING EXCESSIVE COLLAGEN DEPOSITION IN SCLERODERMA AND OTHER FORMS OF DERMAL FIBROSIS.
SHOWS GROWTH-INHIBITORY ACTIVITY ON CULTURES OF ESCHERICHIA COLI & ON GERMINATING SEEDS OF DIFFERENT SPECIES IN WHICH IT DOES NOT NORMALLY OCCUR...
...THIS PROLINE ANALOGUE WHICH INHIBITS COLLAGEN ACCUMULATION IN THE CHICK EMBRYO PRODUCES A DECR IN LUNG EPITHELIAL BUDDING. /OTHER INVESTIGATORS/...PRODUCED FUSIONS OF THE VERTEBRAL BODIES OF RAT FETUSES WHOSE MOTHERS WERE GIVEN 300 MG/KG IP ON DAY 8 /OF GESTATION/. THE USE OF 100 MG/DAY FOR 3 DAY PERIODS DURING ORGANOGENESIS CAUSED NO ILL EFFECTS IN THE FETUSES.
L-AZETIDINE-2-CARBOXYLIC ACID WAS EFFECTIVE IN INDUCING POLYTAIL TUBES ABERRATIONS OF THE T-EVEN BACTERIOPHAGE HEAD IN INFECTED ESCHERICHIA COLI B CULTURES.
L-AZETIDINE-2-CARBOXYLIC ACID WAS INJECTED INTO EMBRYONIC EGGS OF THE COMMON FOWL GALLUS DOMESTICUS AT DAILY DOSES OF 350 MUG/EGG ON 1 OR SEVERAL DAYS BETWEEN 8-12 DAYS OF INCUBATION. TREATMENT AT 9 DAYS OF INCUBATION RETARDED EMBRYONIC GROWTH TO THE 12TH DAY, BUT RECOVERY OF GROWTH RATE OCCURRED BY 15 DAYS OF INCUBATION. ADDITION OF L-AZETIDINE-2-CARBOXYLIC ACID TO THE MEDIUM IN WHICH ALREADY DETERMINED STEM CELLS FROM THE QUADRATOJUGAL WERE CULTURED PREVENTED EXPRESSION OF THE CHONDROGENIC PHENOTYPE.
For more Non-Human Toxicity Excerpts (Complete) data for (L)-AZETIDINE-2-CARBOXYLIC ACID (11 total), please visit the HSDB record page.
UsesSpecific proline antagonist. Used in synthesis of abnormally high molecular weight polypeptides.
UsesL-Azetidine-2-carboxylic acid has been used as a:collagen synthesis inhibitorprotein folding antagonistas a standard in liquid chromatography-mass spectrometry
Uses(S)-(-)-2-Azetidinecarboxylic acid is a four-membered ring analog of L-Proline, It is a useful intermediate in the synthesis of polypeptides,Used in synthesis of abnormally high molecular weight polypeptides.
General DescriptionL-Azetidine-2-carboxylic acid is a non-protein amino acid and teratogenic agent. It is toxic in nature.
DefinitionChEBI: The (S)-enantiomer of azetidine-2-carboxylic acid.