112839-95-9

Basic information

• Product Name: (S)-3-AMINO-2-OXETANONE P-TOLUENESULFONIC ACID SALT
• Synonyms: (S)-3-AMINO-2-OXETANONE P-TOLUENESULFONIC ACID SALT;(S)-3-aminooxetan-2-one 4-methylbenzenesulfonate;(3S)-3-AMino-2-oxetanone 4-Methylbenzenesulfonate;(S)-3-AMino-2-oxetanone 4-Methylbenzenesulfonate;L-Serine β-Lactone Tosylate;(4S)-4-aMinooxetan-2-one;L-Serine b-Lactone Tosylate;(3S)-3-Aminooxetan-2-one
• CAS NO: 112839-95-9
• Molecular Formula: C₃H₅NO₂*C₇H₈O₃S
• Molecular Weight: 259.28
• Mol File: 112839-95-9.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-3-AMINO-2-OXETANONE P-TOLUENESULFONIC ACID SALT(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-AMINO-2-OXETANONE P-TOLUENESULFONIC ACID SALT(112839-95-9)
• EPA Substance Registry System: (S)-3-AMINO-2-OXETANONE P-TOLUENESULFONIC ACID SALT(112839-95-9)

Safety Data

• Hazardous Substances Data: 112839-95-9(Hazardous Substances Data)

Usage

Description

(S)-3-Amino-2-oxetanone p-toluenesulfonic acid salt is a chiral compound that serves as a key intermediate in the synthesis of various pharmaceuticals and biologically active molecules. Its unique structure and properties make it a valuable building block in organic chemistry and drug discovery.

Uses

Used in Pharmaceutical Industry:
(S)-3-Amino-2-oxetanone p-toluenesulfonic acid salt is used as a chiral building block for the synthesis of enantiomerically pure drugs and pharmaceuticals. Its ability to selectively inhibit specific enzymes makes it a promising candidate for the development of novel therapeutic agents.
Used in Organic Chemistry:
(S)-3-Amino-2-oxetanone p-toluenesulfonic acid salt is used as a versatile synthetic intermediate in organic chemistry for the preparation of various chiral compounds, including natural products, agrochemicals, and other biologically active molecules. Its unique structure allows for efficient and selective transformations, facilitating the development of new synthetic routes and methodologies.
Used in Enzyme Inhibition Studies:
(S)-3-Amino-2-oxetanone p-toluenesulfonic acid salt is used as a selective inhibitor of NAAA (N-acylethanolamine-hydrolyzing acid amidase), a key enzyme involved in the regulation of endocannabinoid signaling. Its ability to selectively target and inhibit this enzyme makes it a valuable tool for studying the role of endocannabinoids in various physiological and pathological processes.
Used in Drug Discovery:
(S)-3-Amino-2-oxetanone p-toluenesulfonic acid salt is used as a lead compound in drug discovery efforts, providing a starting point for the development of new therapeutic agents with improved selectivity, potency, and pharmacokinetic properties. Its unique structure and functional groups enable the design and optimization of novel drug candidates targeting a wide range of biological targets and diseases.

Upstream product

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

Downstream Products

• 112839-91-5 L-cysteine dimethylsulfonium bis(p-toluenesulfonic acid) 
• 105661-40-3 L-azidoalanine hydrochloride 
• 88109-06-2 3(S)-<(triphenylmethyl)amino>-2-oxetanone 
• 1237534-81-4 (S)-4-(benzyloxy)-N-(2-oxo-3-oxetanyl)benzamide 
• 1237534-79-0 (S)-(2-oxo-3-oxetanylcarbamoyl)terephthalamic acid phenyl ester 
• 1237534-70-1 (S)-4-ethyl-N-(2-oxo-3-oxetanyl)benzamide 
• 1237534-75-6 (S)-N-(2-oxo-3-oxetanyl)biphenyl-3-carboxamide 
• 1237534-68-7 (S)-N-(2-oxo-3-oxetanyl)benzamide 
• 1142079-64-8 (S)-N-(2-oxooxetan-3-yl)biphenyl-4-carboxamide 
• 83112-06-5 (S)-N-(2-oxo-3-oxetanyl)-2-phenylacetamide 
• 1142079-27-3 (S)-N-(2-oxo-3-oxetanyl)-3-phenylpropionamide 
• 1142079-58-0 (S)-N-(2-oxo-3-oxetanyl)-7-phenylheptanamide 

Relevant articles and documents

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

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.

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