16624-64-9

Basic information

• Product Name: Z-TRP-ONP
• Synonyms: BENZYLOXYCARBONYL-L-TRYPTOPHAN P-NITROPHENYL ESTER;N-ALPHA-BENZYLOXYCARBONYL-L-TRYPTOPHAN-4-NITROPHENYL ESTER;N-BENZYLOXYCARBONYL-L-TRYPTOPHAN-4-NITROPHENYL ESTER;N-CBZ-L-TRYPTOPHAN P-NITROPHENYL ESTER;N-CARBOBENZOXY-L-TRYPTOPHAN-P-NITROPHENYL ESTER;Z-L-TRYPTOPHAN 4-NITROPHENYL ESTER;Z-L-TRYPTOPHAN P-NITROPHENYL ESTER;Z-TRP-ONP
• CAS NO: 16624-64-9
• Molecular Formula: C₂₅H₂₁N₃O₆
• Molecular Weight: 459.45
• EINECS: 240-674-5
• Mol File: 16624-64-9.mol
• Article Data: 1

Chemical Properties

• Melting Point: 102-104 °C
• Boiling Point: 718°Cat760mmHg
• Flash Point: 388°C
• Appearance: /
• Density: 1.371g/cm³
• Vapor Pressure: 1.82E-20mmHg at 25°C
• Refractive Index: 1.666
• Storage Temp.: -15°C
• CAS DataBase Reference: Z-TRP-ONP(CAS DataBase Reference)
• NIST Chemistry Reference: Z-TRP-ONP(16624-64-9)
• EPA Substance Registry System: Z-TRP-ONP(16624-64-9)

Safety Data

• WGK Germany: 3
• F: 3-10-21
• Hazardous Substances Data: 16624-64-9(Hazardous Substances Data)

Usage

General Description

Z-TRP-ONP is a chemical compound consisting of the amino acid tryptophan (TRP) with a protective Z-group and the chromophoric group ONP (o-nitrophenyl). Z-TRP-ONP is commonly used in biochemical and pharmacological research as a substrate in enzyme assays to measure the activity of various peptidases and proteases. The Z-group protects the amino acid from interference by other enzymes and allows for selective measurement of the activity of the specific enzyme being studied. The ONP group provides a chromophoric substrate for convenient measurement of enzyme activity through the detection of the yellow color produced upon cleavage of the compound. Z-TRP-ONP is widely utilized in the study of enzyme kinetics, inhibitor assays, and drug discovery processes.

InChI:InChI=1/C25H21N3O6/c29-24(34-20-12-10-19(11-13-20)28(31)32)23(14-18-15-26-22-9-5-4-8-21(18)22)27-25(30)33-16-17-6-2-1-3-7-17/h1-13,15,23,26H,14,16H2,(H,27,30)

Upstream product

• 100-02-7 4-nitro-phenol 
• 7432-21-5 N-carbobenzyloxy-L-tryptophane 

Downstream Products

• 102249-10-5 N^α-benzyloxycarbonyltryptophylarginylalanine 
• 102249-11-6 N^α-benzyloxycarbonyltryptophylarginylserine 
• 102249-06-9 N^α-benzyloxycarbonyltryptophyl-N^G-nitroarginylalanine p-nitrobenzyl ester 
• 2419-35-4 N-benzyloxycarbonyl-L-tryptophan-L-leucine 
• 1105050-57-4 N-benzyloxycarbonyl-L-tryptophan-L-glutamine 
• 88831-04-3 (S)-2-[(S)-2-benzyloxycarbonylamino-3-(1H-indol-3-yl)-propanoylamino]-5-guanidinopentanoic acid 
• 88831-09-8 L-Tryptophan-L-arginine 
• 68996-89-4 benzyl N-[(1S)-2-[(2-amino-2-oxoethyl)amino]-1-(1H-indol-2-ylmethyl)-2-oxoethyl]carbamate 
• 75511-61-4 C₅₃H₇₃N₁₃O₁₄S₂ 
• 75511-59-0 (benzyloxycarbonyl)-L-prolyl-L-tryptophylglycinamide 
• 38689-27-9 H-Trp-Gly-CONH₂ 
• 7432-21-5 N-carbobenzyloxy-L-tryptophane 
• 17388-70-4 (benzyloxycarbonyl)-L-tryptophylglycine 
• 100-02-7 4-nitro-phenol 

Relevant articles and documents

Tryptophan-containing dipeptide derivatives as potent PPARγ antagonists: Design, synthesis, biological evaluation, and molecular modeling

The discovery of peroxisome proliferator-activated receptor γ (PPARγ) antagonists (also termed "selective PPARγ modulators, SPPARγM") is now of a great interest in the treatment of diabetes and obesity. The structure of compound 1a (G3335, Fig. 1), a novel class of PPARγ antagonist, is entirely different from that of other reported PPARγ antagonists. A series of 35 novel analogues (1b-l, 9a-d, 13a-t) were designed, synthesized and evaluated against the agonistic effects exerted by rosiglitazone. These results indicated that most functional groups of 1a were conserved, and six new compounds (1b, 1c, and 9a-d) exhibited strong PPARγ antagonistic activities (IC50 values of 5.2-25.8 μM) against 10 μM rosiglitazone in the promotion of the PPARγ-LBD-CBP (ligand-binding domain and cAMP-response-element binding protein) interaction as investigated by yeast two-hybrid technology based assay. Molecular modeling studies for compounds 1a-d, 1h, 9c-d, and 13a were also presented.