Nα-Tosyl-L-arginine
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Nα-Tosyl-L-arginine

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Category
L-Amino Acids
Catalog number
BAT-004143
CAS number
1159-15-5
Molecular Formula
C13H20N4O4S
Molecular Weight
328.40
Nα-Tosyl-L-arginine
IUPAC Name
(2S)-5-(diaminomethylideneamino)-2-[(4-methylphenyl)sulfonylamino]pentanoic acid
Synonyms
Tos-L-Arg-OH; Nα-[(4-Methylphenyl)sulfonyl]-L-arginine
Appearance
Solid
Purity
≥ 98% (assay)
Density
1.42 g/cm3
Melting Point
81-103°C
Boiling Point
591.3°C
Storage
Store at 2-8 °C
InChI
InChI=1S/C13H20N4O4S/c1-9-4-6-10(7-5-9)22(20,21)17-11(12(18)19)3-2-8-16-13(14)15/h4-7,11,17H,2-3,8H2,1H3,(H,18,19)(H4,14,15,16)/t11-/m0/s1
InChI Key
KFNRNFXZFIRNEO-NSHDSACASA-N
Canonical SMILES
CC1=CC=C(C=C1)S(=O)(=O)NC(CCCN=C(N)N)C(=O)O

Nα-Tosyl-L-arginine, a versatile biochemical reagent, finds a wide array of applications in both scientific research and industry.

Protease Inhibition Studies: Utilized as a specific inhibitor in investigations of protease enzymes, Nα-Tosyl-L-arginine binds meticulously to the active sites of serine proteases. This binding elucidates the intricate functions and specificities of proteases, offering vital insights crucial for deciphering enzyme kinetics and crafting protease inhibitors with therapeutic potential.

Biochemical Assays: Within various biochemical assays, Nα-Tosyl-L-arginine serves as a standard inhibitor to evaluate protease activity accurately. By aiding in the calibration of assays, this compound ensures precise measurements, particularly valuable in the realm of drug discovery, where the exact quantification of enzyme activity is imperative.

Pharmaceutical Formulation: Embraced by the pharmaceutical industry, Nα-Tosyl-L-arginine plays a pivotal role in formulating advanced drug delivery systems. Its presence enhances the stability and efficacy of treatments based on enzymes, a critical aspect in the development of efficacious therapeutic drugs, particularly those leveraging proteolytic enzymes.

Protein Purification: In the realm of affinity chromatography techniques for protein purification, Nα-Tosyl-L-arginine shines as a key component. By selectively inhibiting proteases during the purification process, it safeguards the integrity of target proteins, ensuring the acquisition of high-purity protein samples essential for in-depth structural and functional studies.

1. Use of a new synthetic substrate, Nalpha-tosyl-L-arginine-P-nitroanilide (TAPA), for determining trypsin activity in the duodenal contents
F Malis, E Kasafírek, P Fric, M Josífko Acta Univ Carol Med Monogr. 1977;(79 Pt 3):131-8.
The newly synthesized chromogenic substrate Nalpha-tosyl-L-arginine-p-nitroanilide (TAPA) was used to determine the trypsin activity (as the concentration and output in 20-min samples) of the duodenal contents before and after hormonal stimulation with cholecystokinin-pancreozymin (CPZ) and secretin (S). The results were compared with those obtained by means of Nalpha-benzoyl-D,L-arginine-p-nitroanilide (BAPA) and the Nalpha-tosyl-L-arginine methylester (TAME). The synthetic substrates were compared in 17 subjects with normal and in 8 subjects with pathological CPZ-S test values. A high degree of correlation was found in every case between the values obtained by means of the given substrates and it actually proved possible to determine the conversion coefficients for the trypsin concentration (BAPA = 1.306 TAPA, TAME = 0.509 TAPA) and for trypsin output (BAPA = 1.306 TAPA, TAME = 0.535 TAPA). The results demonstrate the usefulness of our new chromogenic substrate TAPA, which is more readily available and cheaper than BAPA and TAME for determining trypsin activity in biological material.
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