1784-03-8
Nalpha-4-Tosyl-L-arginine methyl ester hydrochloride
CAS: 1784-03-8
Molecular Formula: C14H23ClN4O4S
1784-03-8 - Names and Identifiers
| Name | Nalpha-4-Tosyl-L-arginine methyl ester hydrochloride |
| Synonyms | TAME Tos-Arg-Ome Hcl Tos-Arg-OMe.HCl Tos-Arg-OMe*HCl Tos-Arg-OMe·HCl Ala-Ala-Ala-OMe Tos-Arg-OMe . HCl L-Ala-L-Ala-L-Ala-OMe Nα-Tosyl-L-arginine methyl·hydrochloric acid N-p-Tosyl-L-arginine methyl ester hydrochloride N-ａ-Tosyl-L-Arginine methyl ester hydrochloride N-4-Tosyl-L-arginine methyl ester hydrochloride na-P-tosyl-L-arginine methyl*ester hydrochloride N-α-p-Tosyl-L-arginine methyl ester hydrochloride N-alpha-Tosyl-L-arginine methyl ester hydrochloride Nalpha-4-Tosyl-L-arginine methyl ester hydrochloride N-alpha-Toluenesulfonylarginine methyl ester hydrochloride |
| CAS | 1784-03-8 |
| EINECS | 217-235-1 |
| 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 |
| InChIKey | JIQFFACVQXXHMY-YDALLXLXSA-N |
1784-03-8 - Physico-chemical Properties
| Molecular Formula | C14H23ClN4O4S |
| Molar Mass | 378.87482 |
| Melting Point | 145-147(lit.) |
| Boling Point | 544.1°C at 760 mmHg |
| Specific Rotation(α) | -14 º (c=4, H2O) |
| Flash Point | 282.9°C |
| Solubility | methanol: 50mg/mL, clear, colorless |
| Vapor Presure | 6.73E-12mmHg at 25°C |
| Appearance | White crystal |
| Color | White |
| BRN | 3922357 |
| Storage Condition | -20°C |
| 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. |
| Refractive Index | -14 ° (C=4, H2O) |
| MDL | MFCD00012578 |
| In vitro study | The absence of APC substrates, TAME hydrochloride ejects Cdc20 from the APC by promoting Cdc20 auto-ubiquitination in its N-terminal region. Cyclin B1 antagonizes TAME hydrochloride's effect by promoting binding of free Cdc20 to the APC and suppressing Cdc20 auto-ubiquitination. TAME hydrochloride stabilizes cyclin B1 in Xenopus extract by two mechanisms. First, it reduces the k cat of the APC Cdc20 /cyclin B1 complex without affecting the K m , slowing the initial ubiquitination of unmodified cyclin B1. Second, as cyclin B1 becomes ubiquitinated, it loses its ability to promote Cdc20 binding to the APC in the presence of TAME hydrochloride. As a result, cyclin B1 ubiquitination terminates before reaching the threshold necessary for proteolysis. |
1784-03-8 - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S37/39 - Wear suitable gloves and eye/face protection S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 3 |
| FLUKA BRAND F CODES | 3-10 |
| HS Code | 29252900 |
1784-03-8 - Introduction
Substrates of trypsin (trypsin), thrombin (thrombin), plasmin (plasmin) and other proteases.
Last Update：2022-10-16 17:14:30
1784-03-8 - Reference Information
| Use | NA-P-toluenesulfonyl-L-arginine methyl ester hydrochloride is a synthetic substrate for serine proteases, so it is used to determine different Serine proteases from organic sources. biochemical research trypsin (trypsin), thrombin (thrombin), plasmin (plasmin) and other protease substrates. |
| Preparation | Using L-arginine and p-methylbenzenesulfonyl chloride as starting materials, adding alcohol as a reaction solvent, one-step preparation of NA-P-toluenesulfonyl-L-arginine methyl ester hydrochloride [1]. The synthesis reaction formula is as follows: Figure 1 NA-P-toluenesulfonyl-L-arginine methyl ester hydrochloride synthesis reaction formula Add 26.25g(0.25mol) of L-arginine and 62.5mL(0.25mol) of 4mol/L sodium hydroxide solution into a 500mL four-mouth flask equipped with mechanical stirring, thermometer, acidity meter and drop-on bottle, and start stirring in a cold trap to completely react arginine and sodium hydroxide, add 2.7g of tetrabutylammonium bisulfate, 50mL of water and methanol to the four-mouth flask and stir to dissolve the phase transfer catalyst, slowly add 42.5mL(0.3mol) of p-methylbenzenesulfonyl chloride below 0 ℃, and continuously add boric acid buffer solution with pH = 9 to adjust the pH at about 9 in the later stage. After dropping p-methylbenzenesulfonyl chloride, the temperature was raised to 15 ℃, the stirring reaction was continued for 3h, and the TLC detection reaction was complete. Wash with ether (2 × 20mL) and discard the ether layer. Under continuous stirring, slowly add 6mol/L hydrochloric acid dropwise, adjust the pH of the aqueous phase to 2, continue stirring for 20min, and precipitate white solid. Ethyl acetate was extracted (3 × 30mL) to separate the organic layer of ethyl acetate. Wash with 5% sodium chloride solution and water to neutral, dry with anhydrous sodium sulfate, and spin evaporate to remove ethyl acetate to obtain oily liquid. Place in the refrigerator and freeze overnight, a large amount of white solids are precipitated out of the oily liquid, a large amount of petroleum ether is added, and the white powdery solid is stirred. Suction filtration, washing and drying with petroleum ether to obtain NA-P-toluenesulfonyl-L-arginine methyl ester hydrochloride. |
| Biological activity | TAME hydrochloride is an inhibitor of the late promotion complex (APC/C or APC), which binds to APC/C and prevents it from passing through Cdc20 and Cdh1 Activation produces mitotic arrest. |
| target | Anaphase-promoting complex (APC) |
Last Update：2024-04-09 02:00:07
Supplier List
Spot supply
Product Name: TAME Visit Supplier Webpage Request for quotationCAS: 1784-03-8
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
Spot supply
Product Name: TAME Visit Supplier Webpage Request for quotationCAS: 1784-03-8
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
View History