21957-58-4

Basic information

• Product Name: N-Tosyl-L-alanine
• Synonyms: (2S)-2-[[(4-Methylphenyl)sulfonyl]aMino]propanoic Acid;N-(Toluene-4-sulfonyl)-L-alanine;N-[(4-Methylphenyl)sulfonyl]-L-alanine;(S)-2-(4-MethylphenylsulfonaMido)propanoic acid
• CAS NO: 21957-58-4
• Molecular Formula: C₁₀H₁₃NO₄S
• Molecular Weight: 243.27952
• Product Categories: Amino Acids & Derivatives
• Mol File: 21957-58-4.mol
• Article Data: 59

Chemical Properties

• Melting Point: 138-139℃
• Boiling Point: 428.9±55.0 °C(Predicted)
• Appearance: /
• Density: 1.319
• Storage Temp.: Refrigerator
• PKA: 3.45±0.10(Predicted)
• CAS DataBase Reference: N-Tosyl-L-alanine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Tosyl-L-alanine(21957-58-4)
• EPA Substance Registry System: N-Tosyl-L-alanine(21957-58-4)

Safety Data

• Hazardous Substances Data: 21957-58-4(Hazardous Substances Data)

Usage

Description

N-Tosyl-L-alanine, with the chemical name N-(4-methylbenzenesulfonyl)-L-alanine and CAS number 21957-58-4, is a white solid compound that plays a significant role in organic synthesis. It is a derivative of L-alanine, an essential amino acid, where the amino group is protected by a tosyl (tosylate) group, which is a toluene sulfonyl group. This protection allows for selective reactions to occur at other sites on the molecule, making it a valuable intermediate in the synthesis of various organic compounds.

Uses

Used in Organic Synthesis:
N-Tosyl-L-alanine is used as a synthetic intermediate for the preparation of various organic compounds. Its tosyl-protected structure allows chemists to perform selective reactions on other functional groups present in the molecule, facilitating the synthesis of complex organic molecules with specific properties and applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-Tosyl-L-alanine can be used as a building block for the synthesis of drug candidates. Its ability to participate in selective reactions makes it a valuable component in the development of new drugs with targeted therapeutic effects.
Used in Research and Development:
N-Tosyl-L-alanine is also utilized in research and development settings, where it can be employed to study the reactivity and selectivity of various organic reactions. This knowledge can be applied to optimize synthetic routes and improve the efficiency of chemical processes.
Used in Chemical Education:
In educational settings, N-Tosyl-L-alanine can serve as a teaching aid to demonstrate the principles of organic synthesis, selective reactions, and the use of protecting groups in the synthesis of complex molecules. This helps students understand the practical applications of organic chemistry in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.

Upstream product

• 87023-89-0 N-(1-(3,5-dimethyl-1H-pyrazol-1-yl)-1-oxopropan-2-yl)-4-methylbenzenesulfonamide 
• 338-69-2 D-Alanine 
• 98-59-9 p-toluenesulfonyl chloride 
• 56-41-7 L-alanin 
• 598-72-1 2-Bromopropionic acid 
• 302-72-7 rac-Ala-OH 
• 104-15-4 toluene-4-sulfonic acid 
• 134340-62-8 N-(1-furan-2-yl-ethyl)-4-methyl-benzenesulfonamide 
• 135822-87-6 (E)-N-(furan-2-ylmethylene)-4-methylbenzenesulfonamide 
• 134452-27-0 (S)-N-tosyl-α'-methyl-α-furfuryl amine 

Downstream Products

• 78221-10-0 4-Methyl-N-{1-[N'-(1H-4-thia-1,2,9,10-tetraaza-anthracen-3-yl)-hydrazinocarbonyl]-ethyl}-benzenesulfonamide 
• 10224-93-8 1,1-bis-(2,5-dimethyl-phenyl)-ethane 
• 186039-99-6 (2S,5S,1'S)-5-hydroxymethyl-2-[1'-(N-tosylamino)ethyl]tetrahydrofuran 
• 186039-98-5 (2S,3S)-2-N-tosylamino-6-hepten-3-ol 
• 186642-59-1 Methanesulfonic acid (1R,2R)-2-methanesulfonyloxy-1-((S)-3-{(2S,5S)-5-[(S)-1-(toluene-4-sulfonylamino)-ethyl]-tetrahydro-furan-2-yl}-3-trimethylsilanyloxy-propyl)-4-((4S,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-butyl ester 
• 186642-23-9 N-((S)-1-{(2S,5S)-5-[(E)-1-Hydroxy-2-(toluene-4-sulfonyl)-7-((4S,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hept-4-enyl]-tetrahydro-furan-2-yl}-ethyl)-4-methyl-benzenesulfonamide 
• 186040-06-2 4-Methyl-N-((S)-1-{(2S,5S)-5-[(E)-2-(toluene-4-sulfonyl)-7-((4S,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hept-4-enoyl]-tetrahydro-furan-2-yl}-ethyl)-benzenesulfonamide 
• 186040-10-8 Methanesulfonic acid (1R,2R,5S,6R)-5,7-dihydroxy-1-((S)-3-hydroxy-3-{(2S,5S)-5-[(S)-1-(toluene-4-sulfonylamino)-ethyl]-tetrahydro-furan-2-yl}-propyl)-2-methanesulfonyloxy-6-methyl-heptyl ester 
• 186040-09-5 N-((S)-1-{(2S,5S)-5-[(1S,4R,5R)-4,5-Dihydroxy-7-((4S,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-1-trimethylsilanyloxy-heptyl]-tetrahydro-furan-2-yl}-ethyl)-4-methyl-benzenesulfonamide 
• 186040-08-4 4-Methyl-N-((S)-1-{(2S,5S)-5-[(E)-(S)-7-((4S,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-1-trimethylsilanyloxy-hept-4-enyl]-tetrahydro-furan-2-yl}-ethyl)-benzenesulfonamide 
• 186040-07-3 4-Methyl-N-((S)-1-{(2S,5S)-5-[(E)-7-((4S,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hept-4-enoyl]-tetrahydro-furan-2-yl}-ethyl)-benzenesulfonamide 
• 186642-43-3 N-((S)-1-{(2S,5S)-5-[(E)-(S)-1-Hydroxy-7-((4S,5R)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hept-4-enyl]-tetrahydro-furan-2-yl}-ethyl)-4-methyl-benzenesulfonamide 
• 186040-11-9 N-{(S)-1-[(2S,5S,2'S,5'S,2''S,5''S)-5''-((R)-2-Hydroxy-1-methyl-ethyl)-dodecahydro-[2,2';5',2'']terfuran-5-yl]-ethyl}-4-methyl-benzenesulfonamide 
• 186040-00-6 (2S,5S,1'S)-5-[1'-(N-tosylamino)ethyl]tetrahydrofuran-2-carbaldehyde 

Relevant articles and documents

Synthesis of Tripeptide Derivatives with Three Stereogenic Centers and Chiral Recognition Probed by Tetraaza Macrocyclic Chiral Solvating Agents Derived from d -Phenylalanine and (1 S,2 S)-(+)-1,2-Diaminocyclohexane via 1H NMR Spectroscopy

Enantiomers of a series of tripeptide derivatives with three stereogenic centers (±)-G1-G9 have been prepared from d- and l-α-amino acids as guests for chiral recognition by 1H NMR spectroscopy. In the meantime, a family of tetraaza macrocyclic chiral solvating agents (TAMCSAs) 1a-1d has been synthesized from d-phenylalanine and (1S,2S)-(+)-1,2-diaminocyclohexane. Discrimination of enantiomers of (±)-G1-G9 was carried out in the presence of TAMCSAs 1a-1d by 1H NMR spectroscopy. The results indicate that enantiomers of (±)-G1-G9 can be effectively discriminated in the presence of TAMCSAs 1a-1d by 1H NMR signals of multiple protons exhibiting nonequivalent chemical shifts (ΔΔδ) up to 0.616 ppm. Furthermore, enantiomers of (±)-G1-G9 were easily assigned by comparing 1H NMR signals of the split corresponding protons with those attributed to a single enantiomer. Different optical purities (ee up to 90%) of G1 were clearly observed and calculated in the presence of TAMCSAs 1a-1d, respectively. Intermolecular hydrogen bonding interactions were demonstrated through theoretical calculations of enantiomers of (±)-G1 with TAMCSA 1a by means of the hybrid functional theory with the standard basis sets of 3-21G of the Gaussian 03 program.

Synthesis, molecular docking and pharmacological investigation of some 4-methylphenylsulphamoyl carboxylic acid analogs

Compounds bearing sulphonyl and amino acid moieties are considered the basis for sulfa drug development. The synthesis of 4-methylphenylsulphamoyl carboxylic acids and the evaluation of their pharmacological activities are reported. The synthesis of these

Synthesis and Structure-Activity Relationships of Arylsulfonamides as AIMP2-DX2 Inhibitors for the Development of a Novel Anticancer Therapy

AIMP2-DX2, a splicing variant of AIMP2, is up-regulated in lung cancer, possesses oncogenic activity, and results in tumorigenesis. Specifically inhibiting the interaction between AIMP2-DX2 and HSP70 to suppress AIMP2-DX2-dependent cancers with small molecules is considered a promising avenue for cancer therapeutics. Optimization of hit BC-DXI-04 (IC50 = 40.1 μM) provided new potent sulfonamide based AIMP2-DX2 inhibitors. Among these, BC-DXI-843 showed improved inhibition against AIMP2-DX2 (IC50 = 0.92 μM) with more than 100-fold selectivity over AIMP2 in a luciferase assay. Several binding assays indicated that this compound effectively induces cancer cell apoptosis by specifically interrupting the interaction between DX2 and HSP70, which leads to the degradation of DX2 via Siah1-mediated ubiquitination. More importantly, BC-DXI-843 demonstrated in vivo efficacy in a tumor xenograft mouse model (H460 cells) at a dosage of 50 mg/kg, suggesting it as a promising lead for development of novel therapeutics targeting AIMP2-DX2 in lung cancer.