2133-34-8

Basic information

• Product Name: (S)-(-)-2-Azetidinecarboxylic acid
• Synonyms: (S)-(-)-2-AZETIDINECARBOXYLIC ACID;(S)-2-AZETIDINE CARBOXYLIC ACID;(S)-(-)-AZETIDINE-2-CARBOXYLIC ACID;(S)-AZETIDINE-2-CARBOXYLIC ACID;(S)-L-2-AZETIDINE CARBOXYLIC ACID;(2S)-(-)-AZETIDINE-2-CARBOXYLIC ACID;L-TRIMETHYLENEIMINE-2-CARBOXYLIC ACID;L-AZETIDINE-2-CARBOXYLIC ACID
• CAS NO: 2133-34-8
• Molecular Formula: C₄H₇NO₂
• Molecular Weight: 101.1
• EINECS: 218-362-5
• Product Categories: Pharmaceutical Raw Materials;Nitrogen cyclic compounds;Miscellaneous;pharmacetical;chiral;API;Amino Acids 13C, 2H, 15N;Carboxylic Acids (Chiral);Azetidines;Chiral Building Blocks;Simple 4-Membered Ring Compounds;Synthetic Organic Chemistry;Amino Acids & Derivatives
• Mol File: 2133-34-8.mol
• Article Data: 13

Chemical Properties

• Melting Point: ~215 °C (dec.)
• Boiling Point: 189.47°C (rough estimate)
• Flash Point: 100.1 °C
• Appearance: White to light beige/Crystalline Powder or Crystals
• Density: 1.2245 (rough estimate)
• Vapor Pressure: 0.0116mmHg at 25°C
• Refractive Index: -122 ° (C=4, H2O)
• Storage Temp.: 2-8°C
• Solubility: Aqueous Base (Slightly), Methanol (Slightly), Water (Slightly)
• PKA: 2.35±0.20(Predicted)
• Water Solubility: 5 g/100 mL
• Merck: 14,908
• BRN: 80678
• CAS DataBase Reference: (S)-(-)-2-Azetidinecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-2-Azetidinecarboxylic acid(2133-34-8)
• EPA Substance Registry System: (S)-(-)-2-Azetidinecarboxylic acid(2133-34-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• RTECS: CM4310500
• Hazardous Substances Data: 2133-34-8(Hazardous Substances Data)

Usage

Description

(S)-(-)-2-Azetidinecarboxylic acid, also known as L-Azetidine-2-carboxylic acid, is a non-protein amino acid and teratogenic agent. It is the (S)-enantiomer of azetidine-2-carboxylic acid and features a four-membered ring structure, making it a unique analog of L-Proline. This white to light yellow crystal powder is toxic in nature and has specific applications in various fields due to its chemical properties.

Uses

Used in Pharmaceutical Industry:
(S)-(-)-2-Azetidinecarboxylic acid is used as a specific proline antagonist for the synthesis of abnormally high molecular weight polypeptides. It serves as a useful intermediate in the creation of these polypeptides, which can have significant implications in drug development and therapeutic applications.
Used in Research and Development:
In the field of research and development, (S)-(-)-2-Azetidinecarboxylic acid is utilized as a collagen synthesis inhibitor and a protein folding antagonist. These properties make it a valuable tool for studying the mechanisms of protein synthesis and folding, which can contribute to the understanding and treatment of various diseases related to protein misfolding.
Used in Analytical Chemistry:
(S)-(-)-2-Azetidinecarboxylic acid is employed as a standard in liquid chromatography-mass spectrometry (LC-MS). Its use as a standard aids in the accurate analysis and identification of other compounds in complex mixtures, ensuring precise and reliable results in various analytical applications.

Biochem/physiol Actions

Azetidine-2-carboxylic acid (AZC) triggers protein aggregation or upregulates the expression of an aggregation-prone mutant protein, upon interference with nascent protein folding.

Safety Profile

Moderately toxic by subcutaneousroute. An experimental teratogen. Other experimentalreproductive effects. When heated to decomposition itemits toxic fumes of NOx.

InChI:InChI=1/C4H7NO2/c6-4(7)3-1-2-5-3/h3,5H,1-2H2,(H,6,7)/t3-/m0/s1

Upstream product

• 69994-45-2 (2S)-1-benzoylazetidine-2-carboxylic acid 
• 247051-66-7 benzyl [1(1S,2S)]-1-(1-phenyl-ethyl)-azetidine-2-carboxylate 
• 869800-26-0 (S)-1-((S)-1-Phenyl-ethyl)-azetidine-2-carboxylic acid; hydrochloride 
• 249734-39-2 methyl (2S,αR)-N-α-methylbenzylazetidine-2-carboxylate 
• 204274-33-9 (2S,1'S)-1-(1'-methyl)benzylazetidine-2-carboxylic acid 
• 921600-20-6 dimethyl (1'S)-1-(1'-methyl)benzylazetidine-2,2-dicarboxylate 
• 307316-14-9 (R)-4-amino-2-chlorobutyric acid 
• 87-69-4 L-Tartaric acid 
• 129740-14-3 tert-butyl (2S)-azetidine-2-carboxylate 
• 485-80-3 S-adenosyl-L-methionine 

Downstream Products

• 96287-28-4 (S)-2-Azetidincarbonsaeure-ethylester-hydrochlorid 
• 34441-14-0 (2S:3'S:3''S)-N-[N-(3-amino-3-carboxypropyl)-3-amino-3-carboxypropyl]-azetidine-2-carboxylic acid 
• 80900-94-3 L-1-<3-(acetylthio)-1-oxopropyl>-2-azetidinecarboxylic acid 
• 51077-14-6 (S)-1-(t-butoxycarbonyl)azetidine-2-carboxylic acid 
• 25654-52-8 (2S)-1-(benzyloxycarbonyl)azetidine-2-carboxylic acid 
• 77856-45-2 (S)-azetidine-2-carboxylic acid benzyl ester 
• 55033-06-2 2(S),3'(S)-N-(3-amino-3-carboxypropyl)-azetidine-2-carboxylic acid 
• 30248-47-6 N-nitrosoazetidine-2-carboxylic acid 
• 69684-70-4 methyl (2S)-azetidine-2-carboxylate 
• 47165-63-9 (S)-1-(2-Benzyloxycarbonylamino-acetyl)-azetidine-2-carboxylic acid 
• 195607-02-4 (S)-1-(4-Benzyloxy-5-methoxy-2-nitro-benzoyl)-azetidine-2-carboxylic acid 
• 104587-62-4 (S)-azetidine-2-methanol 
• 201466-06-0 1-(4-tert-butylbenzenesulfonyl)azetidine-(2S)-carboxylic acid 
• 39897-13-7 (S)-N-(p-toluenesulfonyl)azetidine-2-carboxylic acid 

Relevant articles and documents

Azetidine-Containing Alkaloids Produced by a Quorum-Sensing Regulated Nonribosomal Peptide Synthetase Pathway in Pseudomonas aeruginosa

Pseudomonas aeruginosa displays an impressive metabolic versatility, which ensures its survival in diverse environments. Reported herein is the identification of rare azetidine-containing alkaloids from P. aeruginosa PAO1, termed azetidomonamides, which are derived from a conserved, quorum-sensing regulated nonribosomal peptide synthetase (NRPS) pathway. Biosynthesis of the azetidine motif has been elucidated by gene inactivation, feeding experiments, and biochemical characterization in vitro, which involves a new S-adenosylmethionine-dependent enzyme to produce azetidine 2-carboxylic acid as an unusual building block of NRPS. The mutants of P. aeruginosa unable to produce azetidomonamides had an advantage in growth at high cell density in vitro and displayed rapid virulence in Galleria mellonella model, inferring functional roles of azetidomonamides in the host adaptation. This work opens the avenue to study the biological functions of azetidomonamides and related compounds in pathogenic and environmental bacteria.

Preparation of enantiopure 2-acylazetidines and their reactions with chloroformates

Enantiopure 1-phenylethylazetidine-2-carboxylates and 2-acylazetidines were prepared and reacted with chloroformates to yield α-chloro-γ-amino butyric acid esters and ketones from ring opening reaction of azetidinium ion intermediate in a completely regio- and stereoselective manner.

Practical asymmetric preparation of azetidine-2-carboxylic acid

Facile and straightforward syntheses of both enantiomers of azetidine-2-carboxylic acid are described. The syntheses depart from inexpensive chemicals and allow for the production, in five to six steps, of practical quantities of each enantiomer. Synthetic highlights include the construction of the azetidine ring using an intramolecular alkylation and the use of optically active α-methylbenzylamine as chiral auxiliary.