34235-88-6

Basic information

• Product Name: L-Threonine, N-[(4-methylphenyl)sulfonyl]-
• CAS NO: 34235-88-6
• Molecular Formula: C11H15NO5S
• Molecular Weight: 273.31
• Mol File: 34235-88-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: L-Threonine, N-[(4-methylphenyl)sulfonyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: L-Threonine, N-[(4-methylphenyl)sulfonyl]-(34235-88-6)
• EPA Substance Registry System: L-Threonine, N-[(4-methylphenyl)sulfonyl]-(34235-88-6)

Safety Data

• Hazardous Substances Data: 34235-88-6(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 134019-97-9 N,O-Ditosyl-L-threonine methyl ester 
• 72-19-5 L-threonine 
• 37460-24-5 N^α-Tosyl-L-threo-α,β-diaminobuttersaeure 
• 34235-88-6 N-(toluene-4-sulfonyl)-DL-threonine 
• 80-68-2 DL-threonine 

Downstream Products

• 43188-50-7 N-(toluene-4-sulfonyl)-D_S-threonine 
• 43188-54-1 N-(toluene-4-sulfonyl)-D_S-threonine methyl ester 
• 308365-73-3 (2-Methoxymethoxy-phenyl)-[(2S,3S)-3-methyl-1-(toluene-4-sulfonyl)-aziridin-2-yl]-methanone 
• 308365-75-5 (2-Hydroxy-phenyl)-[(2S,3S)-3-methyl-1-(toluene-4-sulfonyl)-aziridin-2-yl]-methanone 
• 308365-68-6 (2S,3S)-N-Methoxy-N,3-dimethyl-1-(4-tosyl)-2-aziridenecarboxamide 
• 459457-07-9 N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-2-hydroxy-propyl]-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide 
• 459457-11-5 N-(2-hydroxy-1-trityloxymethyl-propyl)-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide 
• 459457-08-0 N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-2-oxo-propyl]-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide 
• 459457-05-7 N-(2-iodo-ethyl)-4-methyl-N-(2,2,4-trimethyl-[1,3]dioxan-5-yl)-benzenesulfonamide 
• 459457-04-6 N-(2-hydroxy-ethyl)-4-methyl-N-(2,2,4-trimethyl-[1,3]dioxan-5-yl)-benzenesulfonamide 
• 459457-06-8 N-(2-hydroxy-1-hydroxymethyl-propyl)-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide 
• 459457-03-5 N-allyl-4-methyl-N-(2,2,4-trimethyl-[1,3]dioxan-5-yl)-benzenesulfonamide 
• 459457-14-8 N-(1-hydroxymethyl-2-oxo-propyl)-N-(2-iodo-ethyl)-4-methyl-benzenesulfonamide 
• 459457-15-9 (2R,3R)-2-hydroxymethyl-3-methyl-1-(toluene-4-sulfonyl)pyrrolidin-3-ol 

Relevant articles and documents

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.

Synthetic studies on polyoxypeptins: Stereoselective synthesis of (2S,3R)-3-hydroxy-3-methylproline using SmI2-mediated cyclization

Stereoselective synthesis of (2S,3R)-3-hydroxy-3-methylproline (3), a component of polyoxypeptins, has been achieved by use of SmI2-mediated diastereoselective cyclization reaction as a key step.

Synthesis of the four stereoisomeric forms of α,β diaminobutyric acid and some derivatives suitable for peptide synthesis

A synthetic route to the four stereo isomers of α,β diaminobutyric acid (α,β-A2bu) has been developed. The L threo, D threo, L erythro and D erythro isomers were prepared from the corresponding threonine and allo threonine isomers. N tosylation under Schotten Baumann conditions was followed by esterification with diazomethane and O tosylation in pyridine to give N,O ditosyl threonine methyl ester (IV). Successive treatments with ammonia saturated methanol and 6N HCl afforded, after several recrystallizations from water, N(α) tosyl α,β diaminobutyric acid (V) of the same configuration as the starting threonine along with racemic mixtures. Presumably, the sulfonamide moiety influenced the steric course of the reaction, causing a double inversion of the C(β) asymmetry center via intermediate aziridine formation. Simultaneous α,β elimination produced the accompanying racemic mixtures via 1 tosylaminocrotonic acid methyl ester. Removal of the tosyl group by the action of sodium in liquid ammonia gave α,β diaminobutyric acid (VI). The configurations of the four isomers were established by NMR and ORD spectra and by conversion of N(α) tosyl L threo α,β diaminobutyric acid (L threo V) to N tosyl L threonine (L threo II) through treatment with nitrous acid. The threo and erythro isomers of α,β A2bu (VI) and N(α) tosyl α,β A2bu (V) were further characterized by their elution behavior on ion exchange colum chromatography (amino acid analyzer) and by their ninhydrin color constants (C(HW)). The erythro isomers of α,β A2bu gave higher color constants (20.6) than the threo isomers (5.6 to 5.8). In the case of N(α) tosyl α,β A2bu, however, the threo isomers produced higher ninhydrin color values (11.3-11.4) than the erythro isomers (1.7 to 1.8). The NMR spectra (in DCl) of N(α) tosyl L threo α,β A2bu (L threo V) exhibited an H(α)-H(β) coupling constant (6.6 Hz) which is identical with that of the erythro isomers of the free amino acid (α,β A2bu). Several derivatives of L threo α,β diaminobutyric acid (L threo VI) suitable for use in peptide synthesis were prepared, including N(α) Tos N(β) Boc α,β A2bu, N(β) Boc α,β A2bu, N(α) Z N(β) Boc α,β A2bu, N(α) Z N(β) Boc α,β A2bu OMe, and N(α) Z α,β A2bu Ome x HCl.