methyl (2S)-5-carbamimidamido-2-(4-methylbenzenesulfonamido)pentanoate hydrochloride

• ChemBase ID: 102795
• Molecular Formular: C14H23ClN4O4S
• Molecular Mass: 378.87482
• Monoisotopic Mass: 378.11285392
• SMILES: Cl.COC(=O)[C@H](CCCNC(=N)N)NS(=O)(=O)c1ccc(C)cc1
• Canonical SMILES: COC(=O)[C@@H](NS(=O)(=O)c1ccc(cc1)C)CCCNC(=N)N.Cl
• InChI: InChI=1S/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/t12-;/m0./s1
• InChIKey: JIQFFACVQXXHMY-YDALLXLXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S)-5-carbamimidamido-2-(4-methylbenzenesulfonamido)pentanoate hydrochloride
• IUPAC Traditional name: TAME hydrochloride; tosyl-L-arginine methyl ester hydrochloride
• Synonyms: TAME hydrochloride; N-α-p-TOSYL-L-ARGININE METHYL ESTER HYDROCHLORIDE; Nα-p-Tosyl-L-arginine methyl ester hydrochloride; (S)-Methyl 5-guanidino-2-(4-methylphenylsulfonamido)pentanoate hydrochloride

Database IDs

• CAS Number: 1784-03-8
• EC Number: 217-235-1
• MDL Number: MFCD00012578
• Beilstein Number: 3922357
• PubChem SID: 162090207; 24900058
• PubChem CID: 2723792

CALCULATED PROPERTIES

• Acid pKa: 10.354648
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -1.8157992
• LogD (pH = 7.4): -1.7515968
• Log P: 0.23181373
• Molar Refractivity: 96.9272 cm^3
• Polarizability: 34.102673 Å^3
• Polar Surface Area: 134.37 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: methanol: soluble50 mg/mL, clear, colorless
• Melting Point: 145-147(lit.); 146-150 °C; 148-150°C
• Optical Rotation: [α]20/D +9.0±1.5°, c = 1% in ethanol

Safety Information

• Storage Condition: 0°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥99.0% (AT); 95+%
• Ignition Residue: ≤0.1%
• Quality: for the determination of trypsin
• Linear Formula: H2NC(=NH)NH(CH2)3CH(NHSO2C6H4CH3)CO2CH3 · HCl

DETAILS

MP Biomedicals - 02103086

Hydrochloride
Crystalline
Enzyme substrate. Also a substrate for plasmin.

Sigma Aldrich - T4626

包装
5, 25, 100 g in poly bottle
Substrates
Substrate for trypsin,1 thrombin,1 plasmin,2 and other proteases.
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.

Sigma Aldrich - 90170

Other Notes
Substrate for the assay of trypsin and thrombin 1; subtilisin2; plasmin3; kallikrein4,5; TAME is not attacked by chymotrypsin.

REFERENCES

• Biochemistry, 11 , 3267 (1972).