17543-58-7

Basic information

• Product Name: Z-P-FLUORO-PHE-OH
• Synonyms: CBZ-L-4-FLUOROPHENYLALANINE;CBZ-4-FLUORO-L-PHE;CBZ-(S)-2-AMINO-3-(4'-FLUOROPHENYL)PROPANOIC ACID;Z-PHE(P-F)-OH;Z-PHE(4-F)-OH;Z-P-FLUORO-PHENYLALANINE;Z-P-FLUORO-PHE-OH;Z-4-FLUORO-L-PHENYLALANINE
• CAS NO: 17543-58-7
• Molecular Formula: C₁₇H₁₆FNO₄
• Molecular Weight: 317.31
• Product Categories: Phenylalanine [Phe, F];Unusual Amino Acids;Z-Amino acid series
• Mol File: 17543-58-7.mol

Chemical Properties

• Melting Point: 158-160℃ (ethyl acetate ligroine )
• Boiling Point: 515.754 °C at 760 mmHg
• Flash Point: 265.718 °C
• Appearance: /
• Density: 1.301 g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Z-P-FLUORO-PHE-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-P-FLUORO-PHE-OH(17543-58-7)
• EPA Substance Registry System: Z-P-FLUORO-PHE-OH(17543-58-7)

Safety Data

• Hazardous Substances Data: 17543-58-7(Hazardous Substances Data)

Usage

Uses

Used in Biochemistry Research:
Z-P-FLUORO-PHE-OH is employed as a biochemical research compound for its role in the advancement of inhibitory activity modeling against cathepsin L, a lysosomal cysteine protease implicated in various pathological conditions.
Used in Pharmaceutical Development:
In the pharmaceutical industry, Z-P-FLUORO-PHE-OH is used as a potential therapeutic agent, particularly for its inhibitory effects on cathepsin L. This makes it a valuable compound in the development of treatments for diseases associated with the overactivity of this protease.
Used in Academic Research:
Z-P-FLUORO-PHE-OH is utilized in academic research settings to study its reactivity and biological role, contributing to a deeper understanding of its potential applications in medicine and other fields.

Upstream product

• 127862-81-1 Z-DL-Phe(4F)-OCH₂CF₃ 
• 49759-55-9 ethyl N-benzyloxycarbonyl-4-fluorophenylalaninate 
• 1132-68-9 L-4-fluorophenylalanine 
• 501-53-1 benzyl chloroformate 
• 394210-36-7 4-(4-fluoro-benzyl)-2,5-dioxo-oxazolidine-3-carboxylic acid benzyl ester 
• 51-65-0 4-Fluorophenylalanine 
• 3005-66-1 diethyl 2-benzyloxycarbonylaminomalonate 
• 49864-41-7 2-Benzyloxycarbonylamino-2-(4-fluoro-benzyl)-malonic acid monoethyl ester 
• 49759-49-1 2-Benzyloxycarbonylamino-2-(4-fluoro-benzyl)-malonic acid diethyl ester 
• 141971-11-1 Z-DL-Phe(4F)OMe 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 

Downstream Products

• 1132-68-9 L-4-fluorophenylalanine 
• 340732-97-0 methyl 2-[(2S)-1-[(2S)-2-[(benzyloxycarbonyl)amino]-3-(4-fluorophenyl)propanoyl]-4-[2-(tert-butoxy)-2-oxoethyl]-3-oxopiperazinyl]acetate 
• 500782-93-4 C₂₁H₂₅FN₂O₅ 
• 500782-95-6 C₁₉H₁₇FN₂O₃ 
• 500782-98-9 C₄₃H₃₇FN₄O₃ 
• 500783-01-7 C₃₅H₃₃FN₄O 
• 500783-06-2 C₄₃H₄₆FN₅O₄ 
• 501010-21-5 C₂₄H₃₂FN₅O₄ 
• 188196-22-7 L-tyrosyl-D-alanyl-p-fluoro-L-phenylalanyl-L-phenylalaninamide 
• 169243-86-1 (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-fluorophenyl)propanoic acid 
• 325958-70-1 {4-tert-butoxycarbonylmethyl-1-[2-(4-carbamimidoyl-benzoylamino)-3-(4-fluoro-phenyl)-propionyl]-3-oxo-piperazin-2-yl}-acetic acid methyl ester 

Relevant articles and documents

Synthesis, in vitro biological activity, hydrolytic stability and docking of new analogs of BIM-23052 containing halogenated amino acids

One of the potent somatostatin analogs, BIM-23052 (DC-23-99) d-Phe-Phe-Phe-d-Trp-Lys-Thr-Phe-Thr-NH2, has established in vitro growth hormone inhibitory activity in nM concentrations. It is also characterized by high affinity to some somatostatin receptors which are largely distributed in the cell membranes of many tumor cells. Herein, we report the synthesis of a series of analogs of BIM-23052 containing halogenated Phe residues using standard solid-phase peptide method Fmoc/OtBu-strategy. The cytotoxic effects of the compounds were tested in vitro against two human tumor cell lines—breast cancer cell line and hepatocellular cancer cell line, as well as on human non-tumorigenic epithelial cell line. Analogs containing fluoro-phenylalanines are cytotoxic in μM range, as the analog containing Phe (2-F) showed better selectivity against human hepatocellular cancer cell line. The presented study also reveals that accumulation of halogenated Phe residues does not increase the cytotoxicity according to tested cell lines. The calculated selective index reveals different mechanisms of antitumor activity of the parent compound BIM-23052 and target halogenated analogs for examined breast tumor cell lines. All peptides tested have high antitumor activity against the HepG2 cell line (IC50 ≈ 100?μM and SI > 5) compared to breast cells. This is probably due to the high permeability of the cell membrane and the higher metabolic activity of hepatocytes. In silico docking studies confirmed that all obtained analogs bind well with the somatostatin receptors with preference to ssrt3 and ssrt5. All target compounds showed high hydrolytic stability at acid and neutral pH, which mimic physiological condition in stomach and human plasma.

PEPTIDOMIMETICS FOR THE TREATMENT OF CORONAVIRUS AND PICORNAVIRUS INFECTIONS

Compounds, compositions and methods for preventing, treating or curing a coronavirus, picornavirus, and/or Hepeviridae virus infection in human subjects or other animal hosts. Specific viruses that can be treated include enteroviruses. In one embodiment, the compounds can be used to treat an infection with a severe acute respiratory syndrome virus, such as human coronavirus 229E, SARS, MERS, SARS-CoV-1 (OC43), and SARS-CoV- 2. In another embodiment, the methods are used to treat a patient co-infected with two or more of these viruses, or a combination of one or more of these viruses and norovirus.

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The α-chymotrypsin-catalyzed peptide synthesis via the kinetically controlled approach using activated esters as acyl donors in orgnanic solvents with low water content was presented. The methyl esters of N-Z derivatives of racemic non-protein amino acids were chosen as carboxy components. They allowed the peptide-bond formation and optical resolution simultaneously to yield homochiral peptides. This method is useful for the incorporation of non-protein amino acids into peptides.

Substituted cyclic carbonyls and derivatives thereof useful as retroviral protease inhibitors

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Porcine Pancreatic Lipase Catalyzed Enantioselective Hydrolysis of Esters of N-Protected Unusual Amino Acids

Porcine pancreatic lipase catalyzed the highly enantioselective hydrolysis of a kind of α-substituted carboxylic esters, i.e., the 2,2,2-trifluoroethyl esters of the N-benzyloxycarbonyl derivatives of unusual amino acids.