149572-97-4

Usage

Uses

Used in Pharmaceutical Synthesis:
(R)-3-Amino-2-oxetanone p-toluenesulfonic acid salt is used as a chiral building block for the production of various pharmaceuticals. Its unique structure and reactivity allow for the creation of complex organic compounds with specific biological activities.
Used in Organic Chemistry Research:
In the field of organic chemistry, (R)-3-Amino-2-oxetanone p-toluenesulfonic acid salt is used as a reagent in chemical reactions to introduce the (R)-3-Amino-2-oxetanone moiety into molecules. This allows for the synthesis of new compounds with potential applications in various industries.
Used in Chemical Reactions:
(R)-3-Amino-2-oxetanone p-toluenesulfonic acid salt is used as a reagent in various chemical reactions to facilitate the introduction of the (R)-3-Amino-2-oxetanone group into target molecules. This enhances the synthesis of complex organic compounds with specific properties and potential applications.
Used in Improving Stability and Solubility:
The p-toluenesulfonic acid salt form of (R)-3-Amino-2-oxetanone improves its stability and solubility, making it easier to handle and use in various applications. This is particularly important in the pharmaceutical industry, where the compound's properties can affect the synthesis process and the final product's quality.
Overall, (R)-3-Amino-2-oxetanone p-toluenesulfonic acid salt is a versatile compound with applications in pharmaceutical synthesis, organic chemistry research, and chemical reactions. Its unique properties and reactivity make it a valuable tool for creating new compounds with potential applications in various industries.

Upstream product

• 98541-64-1 N-(tert-butyloxycarbonyl)-D-serine β-lactone 
• 104-15-4 toluene-4-sulfonic acid 
• 88109-06-2 3(S)-<(triphenylmethyl)amino>-2-oxetanone 
• 98541-64-1 (S)-3-(tert-butoxycarbonylamino)-oxetan-2-one 
• 3262-72-4 (S)-N-(tert-butoxycarbonyl)serine 

Downstream Products

• 105661-40-3 L-azidoalanine hydrochloride 

Relevant academic research and scientific papers

Compositions and methods of inhibiting N-acylethanolamine-hydrolyzing acid amidase

Compounds and pharmaceutical compositions are contemplated that inhibit N-acyl-ethanolamine-hydrolyzing acid amidase (NAAA) to so increase the concentration of the substrate of NAAA, palmitoylethanolamide (PEA). NAAA inhibition is contemplated to be effec

N -(2-Oxo-3-oxetanyl)carbamic acid esters as N-acylethanolamine acid amidase inhibitors: Synthesis and structure-activity and structure-property relationships

The β-lactone ring of N-(2-oxo-3-oxetanyl)amides, a class of N-acylethanolamine acid amidase (NAAA) inhibitors endowed with anti-inflammatory properties, is responsible for both NAAA inhibition and low compound stability. Here, we investigate the structure-activity and structure-property relationships for a set of known and new β-lactone derivatives, focusing on the new class of N-(2-oxo-3-oxetanyl)carbamates. Replacement of the amide group with a carbamate one led to different stereoselectivity for NAAA inhibition and higher intrinsic stability, because of the reduced level of intramolecular attack at the lactone ring. The introduction of a syn methyl at the β-position of the lactone further improved chemical stability. A tert-butyl substituent in the side chain reduced the reactivity with bovine serum albumin. (2S,3R)-2-Methyl-4-oxo-3-oxetanylcarbamic acid 5-phenylpentyl ester (27, URB913/ARN077) inhibited NAAA with good in vitro potency (IC50 = 127 nM) and showed improved stability. It is rapidly cleaved in plasma, which supports its use for topical applications.

Synthesis and structure - Activity relationships of N -(2-Oxo-3-oxetanyl) amides as N -acylethanolamine-hydrolyzing acid amidase inhibitors

The fatty acid ethanolamides (FAEs) are a family of bioactive lipid mediators that include the endogenous agonist of peroxisome proliferator- activated receptor-α, palmitoylethanolamide (PEA). FAEs are hydrolyzed intracellularly by either fatty acid amide hydrolase or N-acylethanolamine- hydrolyzing acid amidase (NAAA). Selective inhibition of NAAA by (S)-N-(2-oxo-3-oxetanyl)-3-phenylpropionamide [(S)-OOPP, 7a] prevents PEA degradation in mouse leukocytes and attenuates responses to proinflammatory stimuli. Starting from the structure of 7a, a series of β-lactones was prepared and tested on recombinant rat NAAA to explore structure-activity relationships (SARs) for this class of inhibitors and improve their in vitro potency. Following the hypothesis that these compounds inhibit NAAA by acylation of the catalytic cysteine, we identified several requirements for recognition at the active site and obtained new potent inhibitors. In particular, (S)-N-(2-oxo-3-oxetanyl)biphenyl-4-carboxamide (7h) was more potent than 7a at inhibiting recombinant rat NAAA activity (7a, IC50 = 420 nM; 7h, IC50 = 115 nM) in vitro and at reducing carrageenan-induced leukocyte infiltration in vivo.

PEPTIDE NUCLEIC ACID CONJUGATES

A novel class of peptide nucleic acids are described which include a conjugate attached thereto. The peptide nucleic acids generally comprise ligands such as naturally occurring DNA bases attached to a peptide backbone through a suitable linker.

Synthesis of chiral 1-(2'-amino-2'-carboxyethyl)-1,4-dihydro-6,7- quinoxaline-2,3-diones: α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionate receptor agonists and antagonists

Recently discovered 6,7-disubstituted quinoxaline-2,3-diones, 1, have been found to antagonize specific binding and functional responses to both α-amino-3-hydroxy-5-methyl-4-isoxazolepropionate (AMPA) and kainic acid. Although a variety of studies have an

Reaction of N-trityl amino acids with BOP: Efficient synthesis of t-butyl esters as well as N-trityl serine- and threonine-β-lactones

Upon exposure to methoxymethylamine and BOP, the stable hydroxybenzotriazolyl amide of TrPheOH was isolated instead of the expected Weinreb amide. This amide behaves as an active amide similar to the Weinreb amide and could be used, among others, for the

Syntheses of optically pure α-amino acids from 3-amino-2-oxetanone salts

A process for the preparation of optically pure α-amino acids comprising the nucleophilic ring-opening of 3-amino-2-oxetanone salts. N-Protected serine β-lactones are deprotected to form heretofore unknown 3-amino-2-oxetanone and its corresponding salts. In turn these previously unknown 3-amino-2-oxetanone salts may be used in the synthesis of other novel or rare stereochemically-pure free amino acids.