37712-76-8

Basic information

• Product Name: (S)-1-acetylazetidine-2-carboxylic acid
• Synonyms: (S)-1-acetylazetidine-2-carboxylic acid
• CAS NO: 37712-76-8
• Molecular Weight: 143.142
• Mol File: 37712-76-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-1-acetylazetidine-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-acetylazetidine-2-carboxylic acid(37712-76-8)
• EPA Substance Registry System: (S)-1-acetylazetidine-2-carboxylic acid(37712-76-8)

Safety Data

• Hazardous Substances Data: 37712-76-8(Hazardous Substances Data)

Usage

General Description

(S)-1-acetylazetidine-2-carboxylic acid, also known as AzeU, is a synthetic amino acid derivative that has sparked interest in the pharmaceutical and chemical industries due to its potential medicinal properties. It is a chiral compound with a unique structure, consisting of a four-membered azetidine ring and an acetyl group. AzeU has been studied for its potential use in drug development, particularly in the treatment of neurological disorders and cancer. Its distinct chemical properties and potential therapeutic applications make it an intriguing subject of research for scientists and drug developers alike.

Upstream product

• 75-36-5 acetyl chloride 
• 2133-34-8 (2S)-azetidine-2-carboxylic acid 
• 108-24-7 acetic anhydride 
• 2517-04-6 Azetidine-2-carboxylic acid 

Relevant articles and documents

Energetic contribution to both acidity and conformational stability in peptide models

The acidity of N-acyl amino acids is dependent upon the rotameric state of the amide bond. In this work we systematically investigated the acidity difference of the rotamers (ΔpKa) in the frames of various acetylated amino acids. Our results indicated a mutual interaction of two carbonyl groups of an attractive type. We observed conservative ΔpKas for acyclic amino acids (2.2-3.0 kJ mol-1), whereas in the case of alicyclic amino acids, the experimental values revealed a strong dependency on the structural context (1.5-4.4 kJ mol-1). In homologous amino acids (α-, β-, γ-, etc.), the strength of the attraction decays in an exponential fashion. Furthermore, the interaction can accumulate through a chain of amide bonds in a cascade fashion, as demonstrated by an Ac-Pro-Pro dipeptide. As a result, we demonstrate that ΔpKa is an experimental parameter to estimate increments in the carbonyl-carbonyl alignment, as determined by the amino acid or peptidyl context. This parameter is also important in understanding the roles of amino acids in both protein folding and translation in biological systems as well as their evolutionary appearance in the genetic code.

Potent, small-molecule inhibitors of human mast cell tryptase. Antiasthmatic action of a dipeptide-based transition-state analogue containing a benzothiazole ketone

Inhibitors of human mast cell tryptase (EC 3.4.21.59) have therapeutic potential for treating allergic or inflammatory disorders. We have investigated transition-state mimetics possessing a heterocycle-activated ketone group and identified in particular benzothiazole ketone (2S)-6 (RWJ-56423) as a potent, reversible, low-molecular-weight tryptase inhibitor with a Ki value of 10 nM. A single-crystal X-ray analysis of the sulfate salt of (2S)-6 confirmed the stereochemistry. Analogues 12 and 15-17 are also potent tryptase inhibitors. Although RWJ-56423 potently inhibits trypsin (Ki = 8.1 nM), it is selective vs other serine proteases, such as kallikrein, plasmin, and thrombin. We obtained an X-ray structure of (2S)-6 complexed with bovine trypsin (1.9-? resolution), which depicts inter alia a hemiketal involving Ser-189, and hydrogen bonds with His-57 and Gln-192. Aerosol administration of 6 (2R,2S; RWJ-58643) to allergic sheep effectively antagonized antigen-induced asthmatic responses, with 70-75% blockade of the early response and complete ablation of the late response and airway hyperresponsiveness.