ChemicalBook > CAS DataBase List > benzyl N-[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(4-methyl-2-oxochromen-7-yl)amino]-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate:hydrochloride

benzyl N-[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(4-methyl-2-oxochromen-7-yl)amino]-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate:hydrochloride

Product Name
benzyl N-[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(4-methyl-2-oxochromen-7-yl)amino]-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate:hydrochloride
CAS No.
70382-26-2
Chemical Name
benzyl N-[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(4-methyl-2-oxochromen-7-yl)amino]-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate:hydrochloride
Synonyms
N-CBZ-Phe-Arg-AMC hydrochloride;Z-Phe-Arg-7-amido-4-methylcoumarin, Hydrochloride - CAS 70382-26-2 - Calbiochem;benzyl N-[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(4-methyl-2-oxochromen-7-yl)amino]-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate:hydrochloride
CBNumber
CB53604365
Molecular Formula
C33H37ClN6O6
Formula Weight
649.15
MOL File
70382-26-2.mol
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benzyl N-[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(4-methyl-2-oxochromen-7-yl)amino]-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate:hydrochloride Property

storage temp. 
-20°C
solubility 
Soluble in DMSO (50 mg/ml)
form 
White to off-white solid
color 
White
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months. Protect from light!
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
C9521
Product name
Z-Phe-Arg-7-amido-4-methylcoumarin, Hydrochloride
Purity
kallikreinsubstrate
Packaging
25mg
Price
$539
Updated
2024/03/01
Sigma-Aldrich
Product number
C9521
Product name
Z-Phe-Arg-7-amido-4-methylcoumarin, Hydrochloride
Purity
kallikreinsubstrate
Packaging
100mg
Price
$1820
Updated
2024/03/01
Sigma-Aldrich
Product number
03-32-1501
Product name
Z-Phe-Arg-7-amido-4-methylcoumarin, Hydrochloride - CAS 70382-26-2 - Calbiochem
Purity
Substrate for fluorogenic assay of plasma and glandular kallikreins.
Packaging
25mg
Price
$167
Updated
2024/03/01
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benzyl N-[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(4-methyl-2-oxochromen-7-yl)amino]-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate:hydrochloride Chemical Properties,Usage,Production

Description

Z-Phe-Arg-AMC (70382-26-2) is a fluorogenic substrate1 for the following cathepsins (kcat/Km in M-1s-1): B (105)2, C/DPP-I (104)3, F (106)4, K/O2 (105)3, L (106)3, L2/V (105)5, O6, S (104)7, X/Z (104)8. The peptide is also cleaved by plasma kallikrein and kallikrein 89, and papain (kcat/Km=105 M-1s-1).3?Excitation: 365nm, Emission: 440nm.5

Uses

Z-Phe-Arg 7-amido-4-methylcoumarin hydrochloride has been used:

  • as a fluorogenic substrate in actinidin inhibition assay
  • as a kallikrein substrate
  • as a trypsin substrate for fluorometric assay
  • as a cathepsin-L substrate

General Description

Substrate for fluorogenic assay of plasma and glandular kallikreins. Also serves as a substrate for cathepsin B, cathepsin L, and papain.

Biochem/physiol Actions

Z-Phe-Arg 7-amido-4-methylcoumarin (Z-FR-AMC) proteolytic lysis by proteases leads to the liberation of AMC resulting in increased fluorescence in the enzymatic reaction.

References

Tavares et al. (2004), Design of potent, selective, and orally bioavailable inhibitors of cysteine protease cathepsin k; J. Med. Chem., 47 588 Therrien et al. (2001), Cathepsins X and B can be differentiated through their respective mono- and dipeptidyl carboxypeptidase activities; Biochemistry, 40 2702 N?gler et al. (1999), Interdependency of sequence and positional specificities for cysteine proteases of the papain family; Biochemistry, 38 4868 Wang et al. (1998), Human cathepsin F. Molecular cloning, functional expression, tissue localization, and enzymatic characterization; J. Biol. Chem., 273 32000 Br?mme et al. (1999), Human cathepsin V functional expression, tissue distribution, electrostatic surface potential, enzymatic characterization and chromosomal localization; Biochemistry, 38 2377 Velasco et al. (1994), Human cathepsin O. Molecular cloning from a breast carcinoma, production of the active enzyme in Escherichia coli, and expression analysis in in human tissues; J. Biol. Chem., 269 27136 Kopitar et al. (1996), Folding and activation of human procathepsin S from inclusion bodies produced in Escherichia coli; Eur. J. Biochem., 236 558 Klemen?i? et al. (2000), Biochemical characterization of human cathepsin X revealed that the enzyme is an exopeptidase, acting as carboxymonopeptidase or carboxydipeptidase; Eur. J. Biochem., 267 5404 Kishi et al. (2006), Activation and enzymatic characterization of recombinant human kallikrein 8; Biol. Chem., 387 723

benzyl N-[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(4-methyl-2-oxochromen-7-yl)amino]-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate:hydrochloride Preparation Products And Raw materials

Raw materials

Preparation Products

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benzyl N-[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(4-methyl-2-oxochromen-7-yl)amino]-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate:hydrochloride Suppliers

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70382-26-2, benzyl N-[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(4-methyl-2-oxochromen-7-yl)amino]-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate:hydrochlorideRelated Search:


  • benzyl N-[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(4-methyl-2-oxochromen-7-yl)amino]-1-oxopentan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate:hydrochloride
  • Z-Phe-Arg-7-amido-4-methylcoumarin, Hydrochloride - CAS 70382-26-2 - Calbiochem
  • N-CBZ-Phe-Arg-AMC hydrochloride
  • 70382-26-2