20063-89-2

Usage

Uses

Used in Pharmaceutical Industry:
DL-Azetidine-2-carboxylic acid is used as a key intermediate for the synthesis of various polypeptides. Its application is crucial in the development of novel drugs and therapeutic agents, particularly in the areas of protein engineering and peptide-based drug design.
Used in Organic Chemistry:
In the field of organic chemistry, DL-Azetidine-2-carboxylic acid is utilized as a building block for the creation of complex organic molecules and structures. Its unique four-membered ring configuration allows for the exploration of new chemical reactions and the synthesis of innovative compounds with potential applications in various industries.
Used in Research and Development:
DL-Azetidine-2-carboxylic acid is also employed in research and development settings, where it is used to study the properties and behavior of four-membered ring compounds. This knowledge can be applied to the design of new materials, catalysts, and other advanced chemical systems.

Upstream product

• 69994-45-2 (2S)-1-benzoylazetidine-2-carboxylic acid 
• 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 
• 485-80-3 S-adenosyl-L-methionine 
• 1758-80-1 L-2,4-diaminobutyrate 
• 25654-51-7 (2R,2S)-1-benzyloxycarbonylazetidine-2-carboxylic acid 
• 186096-46-8 methyl (2R,αR)-N-α-methylbenzylazetidine-2-carboxylate 
• 56-12-2 4-amino-n-butyric acid 
• 22742-42-3 DL-N-diphenylmethylazetidine-2-carboxylic acid benzyl ester 
• 39897-13-7 1-(p-tolylsulfonyl)azetidine-2-carboxylic acid 
• 869800-26-0 (R)-1-((S)-1-Phenyl-ethyl)-azetidine-2-carboxylic acid; hydrochloride 

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 
• 51077-14-6 (S)-1-(t-butoxycarbonyl)azetidine-2-carboxylic acid 
• 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 
• 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 
• 37712-76-8 (S)-1-acetylazetidine-2-carboxylic acid 
• 69994-45-2 (2S)-1-benzoylazetidine-2-carboxylic acid 
• 369596-63-4 (S)-azethidine-2-carboxylic acid N-carboxyamino acid anhydride 
• 369596-63-4 azethidine-2-carboxylic acid N-carboxyamino acid anhydride 

Relevant academic research and scientific papers

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.

Multigram-scale and column chromatography-free synthesis of L-azetidine-2-carboxylic acid for the synthesis of nicotianamine and its derivatives

Multigram-scale synthesis of L-azetidine-2-carboxylic acid from L-aspartic acid was achieved in 13 conventional synthetic steps, without the need for purification by silica-gel column chromatography and expensive reagents. Nicotianamine and its fluorescence-labeled derivatives could be obtained from this synthetic strategy.

Synthesis of 2-carboxylated aza-ring derivatives through α-monohalogenation/ring-contraction of N-sulfonyl lactams

2-Carboxylated aza-rings have been synthesized in two steps through a highly selective monohalogenation of N-sulfonylated lactams of various ring sizes (from 5- to 8-membered rings) followed by a ring contraction reaction. The selective monohalogenation of N-sulfonyl lactams has been achieved in modest to excellent yields (9 examples, 39–96%) using N-halogenosuccinimides via the in situ generation of trimethylsilyl ketene aminal derivatives. The so-obtained α-halogeno N-sulfonyl lactams were engaged in a ring opening/ring closing reaction in the presence of various alcohols or anilines under basic conditions affording 2-carboxylated aza-rings, such as azetidine, pyrrolidine or piperidine derivatives in high yields (24 examples, 61–99%).

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.

Efficient route to (S)-azetidine-2-carboxylic acid

A new and efficient route to (S)-azetidine-2-carboxylic acid (>99.9% ee) in five steps and total yield of 48% via malonic ester intermediates was established. As the key step, efficient four-membered ring formation (99%) was achieved from dimethyl (S)-(1′-methyl)benzylaminomalonate by treating with 1,2-dibromoethane (1.5 eq) and cesium carbonate (2 eq) in DMF. Krapcho dealkoxycarbonylation of dimethyl (1′S)-1-(1′-methyl) benzylazetidine-2,2-dicarboxylate, the product of this cyclization procedure, proceeded with preferential formation (2.7:1, 78% total yield) of the desired (2S,1′S)-monoester, with the help of a chiral auxiliary which was introduced on the nitrogen atom. The undesired (2R,1′S)-isomer could be converted to that with proper stereochemistry, by a deprotonation and subsequent reprotonation step. Finally, lipase-catalyzed preferential hydrolysis of the (2S,1′S)-monoester and subsequent deprotection provided enantiomerically pure (S)-azetidine-2-carboxylic acid in a 91% yield from the mixture of (2S,1′S)- and (2R,1′S)-isomers.

PROCESS FOR PRODUCING OPTICALLY ACTIVE AZETIDINE-2-CARBOXYLIC ACID

The present invention provides an efficient, simple, and commercially advantageous process for producing optically active azetidine-2-carboxylic acid, which is an important material for medicines. The process includes the steps of halogenating an optically active N-protected 4-amino-2-hydroxybutyric acid following inversion of the configuration to produce an optically active N-protected 4-amino-2-halobutyryl halide; hydrolyzing the halide; deprotecting the amino group of the hydrolyzed product to produce an optically active 4-amino-2-halobutyric acid; cyclizing the product in an alkaline aqueous solution; and then protecting the amino group of the cyclized product to produce an optically active N-protected azetidine-2-carboxylic acid. The present invention also provides an optically active N-protected 4-amino-2-halobutyryl halide represented by general formula (2): (wherein P represents a protective group for the primary amino group; * indicates that the carbon atom is asymmetric; and each of X and Y independently represents a halogen atom), which is useful for producing the optically active azetidine-2-carboxylic acid.

Solid-Liquid Biphasic Hydroformylation of Olefins Catalyzed by Rhodium Carhonyl Complexes

Some polymer-anchored alkenes have been hydroformylated by carrying out the reaction in a high-pressure reactor equipped with a suitably designed vial. The solid substrates are converted to the corresponding oxo-aldehydes in high yields. In all cases the regioselectivity was strongly shifted towards the linear aldehyde when the rhodium carbonyl complex was modified with xantphos (3:1 or 4:1 P/Rh molar ratio). Treatment with 5% of trifluoroacetine acid in dichloromethane at room temperature removed quantitatively the oxo-product from the polymer support, which can be purified and reused.

Anti-heparin peptides

The invention concerns a compound exhibiting an anti-heparin activity, of formula Z Bm ! (AXA)x Bn ! (AXA)y Bo (AXA)z Bp, the diagnostic reagents comprising it and the use of said compound in an in vitro diagnostic test of a medicine for anti-heparin activity.