13505-32-3

Basic information

• Product Name: N-(P-TOLUENESULFONYL)-L-PHENYLALANINE
• Synonyms: TOSYL-L-PHENYLALANINE;TOS-PHENYLALANINE-OH;TOS-PHE-OH;P-TOSYL-L-PHENYLALANINE;N-TOSYL-L-PHENYLALANINE;N-P-TOSYL-L-PHENYLALANINE;N-(P-TOLUENESULFONYL)-L-PHENYLALANINE;N-P-TOSYL-L-PHENYLALANINE 97%
• CAS NO: 13505-32-3
• Molecular Formula: C₁₆H₁₇NO₄S
• Molecular Weight: 319.38
• EINECS: 1533716-785-6
• Product Categories: Amino Acid Derivatives;Amino Acids
• Mol File: 13505-32-3.mol

Chemical Properties

• Melting Point: 165 °C
• Boiling Point: 517.7°Cat760mmHg
• Flash Point: 266.9°C
• Appearance: /
• Density: 1.303g/cm³
• Vapor Pressure: 1.52E-11mmHg at 25°C
• Refractive Index: -2.8 ° (C=4.5, Acetone)
• Storage Temp.: Store at RT.
• Solubility: almost transparency in hot EtOH
• PKA: 3.31±0.10(Predicted)
• CAS DataBase Reference: N-(P-TOLUENESULFONYL)-L-PHENYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(P-TOLUENESULFONYL)-L-PHENYLALANINE(13505-32-3)
• EPA Substance Registry System: N-(P-TOLUENESULFONYL)-L-PHENYLALANINE(13505-32-3)

Safety Data

• Safety Statements: 24/25
• HazardClass: IRRITANT
• Hazardous Substances Data: 13505-32-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C16H17NO4S/c1-12-7-9-14(10-8-12)22(20,21)17-15(16(18)19)11-13-5-3-2-4-6-13/h2-10,15,17H,11H2,1H3,(H,18,19)

Upstream product

• 591-51-5 phenyllithium 
• 88452-86-2 (2S)-N-para-toluenesulfonylaziridine-2-carboxylic acid 
• 63-91-2 L-phenylalanine 
• 104-15-4 toluene-4-sulfonic acid 
• 918886-05-2 N-(p-toluenesulfonyl) phenylalanine (9-methoxy-3-oxo-3H-benzo[f]benzopyran-1-yl) methyl ester 
• 98-59-9 p-toluenesulfonyl chloride 
• 88955-90-2 7-(N-tosyl-L-phenylalanyl)amino-4-nitrobenzo-2-oxa-1,3-diazole 
• 818-72-4 1-Octyn-3-ol 
• 90365-18-7 N-(p-toluenesulfonyl)-L-phenylalanyl chloride 

Downstream Products

• 90365-18-7 N-(p-toluenesulfonyl)-L-phenylalanyl chloride 
• 63-91-2 L-phenylalanine 
• 267885-96-1 1-(p-Toluenesulphonyl)-5-benzyl-2-thiohydantoin 
• 197641-32-0 (S)-2-[(2-tert-Butoxycarbonylamino-ethyl)-(toluene-4-sulfonyl)-amino]-3-phenyl-propionic acid benzyl ester 
• 74974-71-3 (2S)-2-(N-benzyl-p-toluenesulfonamido)-3-phenylpropanal 
• 74974-77-9 (2S)-(Z)-N,N-benzyl-2-(4,5-dimethyl-1-phenyl)hexa-3,5-dienylamine 
• 74974-78-0 (2S)-(E)-N,N-benzyl-2-(4,5-dimethyl-1-phenyl)hexa-3,5-dienylamine 
• 74974-70-2 (2S)-2-(N-benzyl-p-toluenesulfonamido)-3-phenylpropanol 
• 74974-75-7 (2S)-(Z)-N,N-benzyl-2-(4,5-dimethyl-1-phenyl)hexa-3,5-dienyl-p-toluenesulfonamide 
• 74974-80-4 (2S)-(E)-N,N-benzyl-2-(4,5-dimethyl-1-phenyl)hexa-3,5-dienyl-p-toluenesulfonamide 
• 74974-81-5 (2'S)-3,3-dimethyl-6-oxocyclohex-1-enyl-1-((Z)-N,N-benzyl-2'-<4',5'-dimethyl-1'-phenyl>hexa-3',5'-dienyl)carboxamide 
• 74974-74-6 (5S)-(Z)-5-(N-benzyl-p-toluenefulfonamido)-2,3-dimethyl-6-phenylhex-3-en-2-ol 
• 74974-79-1 (5S)-(E)-5-(N-benzyl-p-toluenefulfonamido)-2,3-dimethyl-6-phenylhex-3-en-2-ol 
• 74974-82-6 (3S,3aR,6aS,10aS)-3,3a,6,6a,7,8,9,10-octahydro-2,3-dibenzyl-4,5,7,7-tetramethyl-1H-benzisoindole-1,10-dione 

Relevant articles and documents

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Synthesis, characterization and cytotoxicity of mixed-ligand complexes of palladium(II) with aromatic diimine and 4-toluenesulfonyl-l-amino acid dianion

Eight new palladium(II) complexes (1a-2d) with 4-toluenesulfonyl-l-amino acid dianion and diimine (bipy and phen) have been synthesized and characterized by elemental analysis, IR, UV, 1H NMR, 13C NMR and mass spectra techniques. Cry

Synthesis and Structural Characterization of Trivalent Amino Acid Derived Chiral Phosphorus Compounds

Reaction of the N-toluenesulfonyl derivatives of (S)-alanine, phenylalanine, and valine (4-6) with PhPCl2 gave in high yield the 4-methyl, benzyl, and isopropyl derivatives (7-9) of 2-phenyl-1-p-toluenesulfonyl-1,3,2-oxazaphospholidin-5-one. Th

SYNTHESIS OF OPTICALLY PURE ALKYNOLS

(R,S)-1-alkylprop-2-yn-1-ols have been separated by a 2-step procedure, esterification with N-p-tosyl-(L)-phenylalanine (or valine), recrystallisation of the diastereomeric esters from ethanol/hexane and saponification of the optically pure esters.

Synthesis, characterization and cytotoxicity of mixed-ligand complexes of palladium(II) with 2, 2′-biquinoline/1, 4-diaminobutane and 4-toluenesulfonyl-L-amino acid dianion

Seven new palladium(II) complexes (1-7) with 4-toluenesulfonyl-L-amino acid dianion and 2, 2′-biquinoline (bqu)/1,4-diaminobutane (dab) have been synthesized and characterized by elemental analysis, IR, 1H NMR, and mass spectra techniques. Crys

Design and synthesis of tripeptidyl furylketones as selective inhibitors against the β5 subunit of human 20S proteasome

A series of tripeptidic proteasome inhibitors with furylketone as C-terminus were designed and synthesized. Biochemical evaluations against β1, β2 and β5 subunits revealed that they acted selectively on β5 subunit with IC50s against chymotrypsin-like (CT-L) activity in micromolar range. LC-MS/MS analysis of the ligand-20S proteasome mixture showed that the most potent compound 11m (IC50 = 0.18 μM) made no covalent modification on 20S proteasome. However, it was identified acting in a slowly reversible manner in wash-out assay and the reversibility was much lower than that of MG132, suggesting the possibility of these tripeptidic furylketones forming reversible covalent bonds with 20S proteasome. Several compounds were selected for anti-proliferative assay towards multiple cancer cell lines, and compound 11m displayed comparable potency to positive control (MG132) in all cell lines tested. Furthermore, the pharmacokinetic (PK) data in rats indicated 11m behaved similarly (Cmax, 2007 μg/L; AUC0?t, 680 μg/L·h; Vss, 0.66 L/kg) to the clinical used agent carfilzomib. All these data suggest 11m is a good lead compound to be developed to novel anti-tumor agent.

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.

Synthesis and hetero-Diels-Alder reactions of enantiomerically pure dihydro-1: H -azepines

Thermolysis of enantiomerically pure 3-substituted 7,7-dihalo-2-azabicyclo[4.1.0]heptanes in the presence of K2CO3 gives in good yields 2-alkyl-6-halo-1-tosyl-2,3-dihydro-1H-azepines. These undergo highly stereoselective [4+2] cycloaddition reactions with heterodienophiles and arylation/alkenylation under Suzuki conditions.

Enantioselective vinylation of aldehydes with the vinyl Grignard reagent catalyzed by magnesium complex of chiral BINOLs

Enantioselective vinylation of aldehydes via direct catalytic asymmetric Grignard reaction of aldehdyes and the vinyl Grinard reagent is a long-standing challenge. This work demonstrated that the magnesium (S)-3,3′-dimethyl BINOLate enantioselectively catalyze the direct vinylation of aldehydes with the deactivated vinylmagnesium bromide by bis(2-[N,N′-dimethylamino]ethyl) ether (BDMAEE) in the addition of n-butylmagnesium chloride. The highest ee of 63% was achieved up to date.

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The synthesis of a crystalline ethynyl-1,2-benziodoxol-3(1H)-one (EBX)-acetonitrile complex is described. EBX has been widely used as an active species for a variety of reactions; however, its high instability has so far prevented its isolation. The EBX-acetonitrile is self-assembled into a double-layered honeycomb structure through weak hypervalent iodine secondary interactions and hydrogen bonding. The N-ethynylation of a variety of sulfonamides using the EBX-acetonitrile complex as a substrate under mild conditions is also described.