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

Uses

L-Serine β-Lactone is a selective inhibitor of NAAA (N-acylethanolamine-hydrolyzing acid amidase). A number of serine and threonine β-lactones were tested against HAV 3C proteinase.

Upstream product

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

Downstream Products

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

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