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20063-89-2

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20063-89-2 Usage

Chemical Properties

White Crystalline Solid

Uses

DL-Azetidine-2-carboxylic acid is a four-membered ring analog of L-Proline,it is a useful intermediate in the synthesis of polypeptides.

Check Digit Verification of cas no

The CAS Registry Mumber 20063-89-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,0,0,6 and 3 respectively; the second part has 2 digits, 8 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 20063-89:
(7*2)+(6*0)+(5*0)+(4*6)+(3*3)+(2*8)+(1*9)=72
72 % 10 = 2
So 20063-89-2 is a valid CAS Registry Number.

20063-89-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name Azetidine-2-carboxylic acid

1.2 Other means of identification

Product number -
Other names D,L-AZETIDINE-2-CARBOXYLIC ACID

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:20063-89-2 SDS

20063-89-2Relevant articles and documents

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Leete

, p. 3162 (1964)

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

Hong, Zhilai,Bolard, Arnaud,Giraud, Caroline,Prévost, Sébastien,Genta-Jouve, Grégory,Deregnaucourt, Christiane,H?ussler, Susanne,Jeannot, Katy,Li, Yanyan

, p. 3178 - 3182 (2019)

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.

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

Sirindil, Fatih,Miaskiewicz, Solène,Kern, Nicolas,Lalaut, Arno,Felten, Anne-Sophie,Weibel, Jean-Marc,Pale, Patrick,Blanc, Aurélien

, p. 5096 - 5106 (2017/07/28)

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%).

Practical asymmetric preparation of azetidine-2-carboxylic acid

Couty, Francois,Evano, Gwilherm,Vargas-Sanchez, Monica,Bouzas, Gloria

, p. 9028 - 9031 (2007/10/03)

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.

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