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

Chemical Properties

white to light yellow crystal powder

Uses

Different sources of media describe the Uses of 2133-34-8 differently. You can refer to the following data:
1. Specific proline antagonist. Used in synthesis of abnormally high molecular weight polypeptides.
2. (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.
3. L-Azetidine-2-carboxylic acid has been used as a:collagen synthesis inhibitorprotein folding antagonistas a standard in liquid chromatography-mass spectrometry

Definition

ChEBI: The (S)-enantiomer of azetidine-2-carboxylic acid.

General Description

L-Azetidine-2-carboxylic acid is a non-protein amino acid and teratogenic agent. It is toxic in nature.

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

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

Downstream Products

• 195607-02-4 (S)-1-(4-Benzyloxy-5-methoxy-2-nitro-benzoyl)-azetidine-2-carboxylic acid 
• 128120-94-5 (S)-Azetidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-(2-oxo-2-phenyl-ethyl) ester 
• 161511-85-9 2-(S)-hydroxymethyl-azetidine-1-carboxylic acid tert-butyl ester 
• 69994-45-2 (2S)-1-benzoylazetidine-2-carboxylic acid 
• 958350-50-0 C₂₀H₂₈N₂O₇ 
• 90599-96-5 C₁₃H₂₂N₂O₆ 
• 104587-62-4 (S)-azetidine-2-methanol 
• 47165-63-9 (S)-1-(2-Benzyloxycarbonylamino-acetyl)-azetidine-2-carboxylic acid 
• 69684-70-4 methyl (2S)-azetidine-2-carboxylate 
• 30248-47-6 N-nitrosoazetidine-2-carboxylic acid 
• 55033-06-2 2(S),3'(S)-N-(3-amino-3-carboxypropyl)-azetidine-2-carboxylic acid 
• 34441-14-0 (2S:3'S:3''S)-N-[N-(3-amino-3-carboxypropyl)-3-amino-3-carboxypropyl]-azetidine-2-carboxylic acid 
• 77856-45-2 (S)-azetidine-2-carboxylic acid benzyl ester 
• 25654-52-8 (2S)-1-(benzyloxycarbonyl)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.