Fmoc-D-Phe(4-CF3)-OH - 238742-88-6

Fmoc-D-Phe(4-CF3)-OH

Catalog Number: EVT-251110
CAS Number: 238742-88-6
Molecular Formula: C25H20F3NO4
Molecular Weight: 455.4 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description
Fmoc-D-Phe(4-CF3)-OH is a chemical compound that has gained significant attention in the field of medical research due to its potential therapeutic effects. It is a derivative of phenylalanine, an essential amino acid that plays a crucial role in protein synthesis. Fmoc-D-Phe(4-CF3)-OH is a modified form of phenylalanine that has a trifluoromethyl group attached to it. This modification enhances its bioactivity and potency, making it a promising candidate for drug development.
Applications in Various Fields
In medical research, Fmoc-D-Phe(4-CF3)-OH has been studied for its role in drug development. It has been shown to have potent analgesic effects and can act as a selective antagonist of the mu-opioid receptor. This receptor is involved in the regulation of pain and is a target for many pain medications. Fmoc-D-Phe(4-CF3)-OH has also been studied for its potential use in the treatment of inflammatory conditions.
In environmental research, Fmoc-D-Phe(4-CF3)-OH has been studied for its effects on ecosystems. It has been shown to have low toxicity and is not expected to have significant environmental impacts. However, more research is needed to fully understand its effects on the environment.
In industrial research, Fmoc-D-Phe(4-CF3)-OH has been used in manufacturing processes to improve product quality and efficiency. Health and safety considerations are essential when using Fmoc-D-Phe(4-CF3)-OH in industrial settings.

Properties

CAS Number

238742-88-6

Product Name

Fmoc-D-Phe(4-CF3)-OH

IUPAC Name

2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[4-(trifluoromethyl)phenyl]propanoic acid

Molecular Formula

C25H20F3NO4

Molecular Weight

455.4 g/mol

InChI

InChI=1S/C25H20F3NO4/c26-25(27,28)16-11-9-15(10-12-16)13-22(23(30)31)29-24(32)33-14-21-19-7-3-1-5-17(19)18-6-2-4-8-20(18)21/h1-12,21-22H,13-14H2,(H,29,32)(H,30,31)

InChI Key

YMEGJWTUWMVZPD-JOCHJYFZSA-N

SMILES

C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CC=C(C=C4)C(F)(F)F)C(=O)O

Synonyms

238742-88-6;Fmoc-4-(trifluoromethyl)-D-phenylalanine;Fmoc-D-Phe(4-CF3)-OH;FMOC-D-4-Trifluoromethylphe;Fmoc-D-4-Trifluoromethylphenylalanine;Fmoc-4-Trifluoromethyl-D-Phenylalanine;(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[4-(trifluoromethyl)phenyl]propanoicacid;(R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-(trifluoromethyl)phenyl)propanoicacid;Fmoc-L-phe(4-CF3)-OH;(2R)-2-([(9H-FLUOREN-9-YLMETHOXY)CARBONYL]AMINO)-3-[4-(TRIFLUOROMETHYL)PHENYL]PROPANOICACID;(2R)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-3-[4-(trifluoromethyl)phenyl]propanoicacid;AC1MCRUC;47834_ALDRICH;SCHEMBL2304915;N-{[(9H-Fluoren-9-yl)methoxy]carbonyl}-4-(trifluoromethyl)-L-phenylalanine;47834_FLUKA;CTK8C5619;MolPort-001-775-721;(2S)-2-({[(9H-Fluoren-9-yl)methoxy]carbonyl}amino)-3-[4-(trifluoromethyl)phenyl]propanoicacid;ZINC2569519;CF-651;MFCD00797582;AKOS015837372;AKOS015895489;AB07189

Canonical SMILES

C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CC4=CC=C(C=C4)C(F)(F)F)C(=O)O

Isomeric SMILES

C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@H](CC4=CC=C(C=C4)C(F)(F)F)C(=O)O
Method of Synthesis or Extraction
Fmoc-D-Phe(4-CF3)-OH can be synthesized using various methods, including solid-phase peptide synthesis (SPPS) and solution-phase peptide synthesis. SPPS is the most commonly used method for synthesizing peptides and involves the stepwise addition of amino acids to a growing peptide chain. The efficiency and yield of SPPS depend on several factors, including the quality of the starting materials, the reaction conditions, and the purification methods used. SPPS has been shown to be highly efficient, with yields ranging from 70% to 95%. However, it can be time-consuming and requires specialized equipment and expertise.
Solution-phase peptide synthesis is another method used for synthesizing Fmoc-D-Phe(4-CF3)-OH. This method involves the use of a solution of amino acids and reagents to synthesize the peptide. The efficiency and yield of solution-phase peptide synthesis depend on the reaction conditions and the purification methods used. This method is less commonly used than SPPS but can be useful for synthesizing peptides with specific modifications.
Environmental and safety considerations are essential when synthesizing Fmoc-D-Phe(4-CF3)-OH. The use of hazardous chemicals and solvents can pose a risk to the environment and human health. Therefore, it is crucial to follow proper safety protocols and dispose of waste materials appropriately.
Chemical Structure and Biological Activity
Fmoc-D-Phe(4-CF3)-OH has a chemical structure that consists of a phenylalanine residue with a trifluoromethyl group attached to the para position of the phenyl ring. This modification enhances its bioactivity and potency, making it a promising candidate for drug development.
The mechanism of action and biological targets of Fmoc-D-Phe(4-CF3)-OH are not well understood. However, studies have shown that it has potent analgesic effects and can act as a selective antagonist of the mu-opioid receptor. This receptor is involved in the regulation of pain and is a target for many pain medications.
Biological Effects
Fmoc-D-Phe(4-CF3)-OH has been shown to have significant effects on cell function and signal transduction. It has been shown to inhibit the release of neurotransmitters involved in pain signaling, such as substance P and glutamate. This inhibition leads to a reduction in pain perception and can be useful in the treatment of chronic pain.
Potential therapeutic and toxic effects of Fmoc-D-Phe(4-CF3)-OH are still being studied. However, studies have shown that it has potent analgesic effects and can act as a selective antagonist of the mu-opioid receptor. This receptor is involved in the regulation of pain and is a target for many pain medications. Fmoc-D-Phe(4-CF3)-OH has also been shown to have anti-inflammatory effects, making it a potential candidate for the treatment of inflammatory conditions.
Future Perspectives and Challenges
Current limitations in the use and study of Fmoc-D-Phe(4-CF3)-OH include a lack of understanding of its mechanism of action and biological targets. More research is needed to fully understand its potential therapeutic effects and toxic effects.
Possible solutions and improvements include the development of new methods for synthesizing Fmoc-D-Phe(4-CF3)-OH and the identification of its biological targets. Future trends and prospects in the application of Fmoc-D-Phe(4-CF3)-OH in scientific research include its potential use in the development of new pain medications and anti-inflammatory drugs.

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