1784-03-8

Basic information

• Product Name: TOS-ARG-OME HCL
• Synonyms: P-TOSYL-L-ARG METHYL ESTER HCL;P-TOLUENESULFONYL-L-ARGININE METHYL ESTER HCL;P-TOLUENESULFONYL-L-ARGININE METHYL ESTER HYDROCHLORIDE;N-P-TOSYL-L-ARGININE METHYL ESTER HYDROCHLORIDE;N-ALPHA-4-TOSYL-L-ARGININE METHYL ESTER HYDROCHLORIDE;N-ALPHA-TOLUENESULFONYLARGININE METHYL ESTER HYDROCHLORIDE;NALPHA-TOSYL-L-ARGININE METHYL ESTER HYDROCHLORIDE;N-ALPHA-TOSYL-L-ARGININE METHYL ESTER HYDROCHLORIDE SALT
• CAS NO: 1784-03-8
• Molecular Formula: C₁₄H₂₂N₄O₄S*ClH
• Molecular Weight: 378.87482
• EINECS: 217-235-1
• Product Categories: Amino Acids;Arginine [Arg, R];Amino Acids and Derivatives;Amino hydrochloride
• Mol File: 1784-03-8.mol
• Article Data: 0

Chemical Properties

• Melting Point: 145-147(lit.)
• Boiling Point: 544.1 °C at 760mmHg
• Flash Point: 282.9 °C
• Appearance: White/Fine Crystalline Powder
• Vapor Pressure: 6.73E-12mmHg at 25°C
• Refractive Index: -14 ° (C=4, H2O)
• Storage Temp.: −20°C
• Solubility: methanol: 50 mg/mL, clear, colorless
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 3 months.
• BRN: 3922357
• CAS DataBase Reference: TOS-ARG-OME HCL(CAS DataBase Reference)
• NIST Chemistry Reference: TOS-ARG-OME HCL(1784-03-8)
• EPA Substance Registry System: TOS-ARG-OME HCL(1784-03-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 1784-03-8(Hazardous Substances Data)

Usage

Description

TOS-ARG-OME HCL, also known as N-4-Tosyl-L-arginine Methyl Ester Hydrochloride, is a white fine crystalline powder with significant applications in the field of biochemistry and pharmaceuticals. It is primarily recognized for its role as an enzyme inhibitor and a synthetic substrate for various proteases, including trypsin, thrombin, and plasmin.

Uses

Used in Pharmaceutical Industry:
TOS-ARG-OME HCL is used as an enzyme inhibitor for its ability to bind to the ubiquitin ligase anaphase-promoting complex (APC), preventing its activation by Cdc20 and Cdh1, and resulting in mitotic arrest. This property makes it a valuable tool in the study and development of treatments for various diseases.
Used in Biochemical Research:
As a synthetic substrate for serine proteases, TOS-ARG-OME HCL is used to determine the activity and presence of these enzymes from diverse organic sources. This application is crucial in understanding the role of serine proteases in biological processes and their potential as therapeutic targets.
Used in Diagnostics:
In the diagnostics industry, TOS-ARG-OME HCL serves as a valuable reagent for the detection and measurement of protease activity. Its specificity for serine proteases allows for accurate assessment of enzyme function and can aid in the diagnosis of conditions related to abnormal protease activity.
Used in Drug Development:
In the development of new drugs, TOS-ARG-OME HCL can be employed as a starting point for the design of inhibitors targeting serine proteases. By understanding the interactions between this compound and its target enzymes, researchers can develop more effective and selective drugs for various therapeutic applications.
Overall, TOS-ARG-OME HCL is a versatile compound with a wide range of applications in the pharmaceutical, biochemical research, diagnostics, and drug development industries. Its unique properties as an enzyme inhibitor and synthetic substrate make it an essential tool in the study and treatment of various diseases and conditions.

Biochem/physiol Actions

Nα-p-Tosyl-L-arginine methyl ester (TAME) binds to anaphase-promoting complex (APC) and prevents its activation by Cdc20 and Cdh1.

References

1) Zeng et al. (2010) Pharmacologic inhibition of the anaphase-promoting complex induces a spindle checkpoint-dependent mitotic arrest in the absence of spindle damage; Cancer Cell, 18 382 2) Zeng and King (2012) An APC/C inhibitor stabilizes Cyclin B1 by prematurely terminating ubiquitination; Nat. Chem. Biol., 8 383

InChI:InChI=1/C14H22N4O4S.ClH/c1-10-5-7-11(8-6-10)23(20,21)18-12(13(19)22-2)4-3-9-17-14(15)16;/h5-8,12,18H,3-4,9H2,1-2H3,(H4,15,16,17);1H

Upstream product

• 67-56-1 methanol 
• 1159-15-5 N^α-p-tosyl-L-arginine 
• 74-79-3 L-arginine 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 14279-64-2 N^α-(toluene-4-sulfonyl)-L-arginine amide; hydrochloride 
• 1159-15-5 N^α-p-tosyl-L-arginine