Fmoc-L-4-Bromophenylalanine - 198561-04-5

Fmoc-L-4-Bromophenylalanine

Catalog Number: EVT-251131
CAS Number: 198561-04-5
Molecular Formula: C24H20BrNO4
Molecular Weight: 466.3 g/mol
The product is for non-human research only. Not for therapeutic or veterinary use.
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Product Introduction

Description
Fmoc-L-4-Bromophenylalanine is a modified amino acid that has gained significant attention in the field of medicinal chemistry. It is a derivative of phenylalanine, an essential amino acid that plays a crucial role in protein synthesis. Fmoc-L-4-Bromophenylalanine is widely used in the synthesis of peptides and proteins due to its unique chemical properties. This paper aims to provide a comprehensive review of Fmoc-L-4-Bromophenylalanine, including its method of synthesis, chemical structure, biological activity, potential therapeutic and toxic effects, applications in medical, environmental, and industrial research, and future perspectives and challenges.
Applications in Various Fields
Fmoc-L-4-Bromophenylalanine has various applications in medical, environmental, and industrial research. In medical research, Fmoc-L-4-Bromophenylalanine plays a crucial role in drug development, including the design and synthesis of peptide-based drugs and the optimization of drug delivery systems. It has also been investigated in clinical trials for the treatment of various diseases, including cancer, infectious diseases, and neurological disorders. In environmental research, Fmoc-L-4-Bromophenylalanine can be used to study the effects of pollutants on ecosystems and to develop sustainable pollution management strategies. In industrial research, Fmoc-L-4-Bromophenylalanine can be used to improve product quality and efficiency, as well as to ensure health and safety considerations in manufacturing processes.

Properties

CAS Number

198561-04-5

Product Name

Fmoc-L-4-Bromophenylalanine

IUPAC Name

(2S)-3-(4-bromophenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid

Molecular Formula

C24H20BrNO4

Molecular Weight

466.3 g/mol

InChI

InChI=1S/C24H20BrNO4/c25-16-11-9-15(10-12-16)13-22(23(27)28)26-24(29)30-14-21-19-7-3-1-5-17(19)18-6-2-4-8-20(18)21/h1-12,21-22H,13-14H2,(H,26,29)(H,27,28)/t22-/m0/s1

InChI Key

TVBAVBWXRDHONF-QFIPXVFZSA-N

SMILES

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

Synonyms

198561-04-5;(S)-N-Fmoc-4-bromophenylalanine;Fmoc-L-4-Bromophenylalanine;FMOC-PHE(4-BR)-OH;Fmoc-4-bromo-L-phenylalanine;FMOC-L-4-BROMOPHE;Fmoc-L-phe(4-Br)-OH;FMOC-P-BROMO-PHE-OH;FMOC-L-4-BR-PHE-OH;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(4-bromophenyl)propanoicacid;Fmoc-D-4-Bromophenylalanine;N-(9-FLUORENYLMETHOXYCARBONYL)-4-BROMOPHENYL-L-ALANINE;(S)-N-(9-FLUORENYLMETHOXYCARBONYL)-(4-BROMOPHENYL)ALANINE;(2S)-3-(4-bromophenyl)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoicacid;(2S)-3-(4-bromophenyl)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}propanoicacid;4-Bromo-L-phenylalanine,N-FMOCprotected;PubChem23291;FMOC-PBR-L-PHE-OH;AC1MC15X;KSC185K3R;MLS001074424;SCHEMBL119803;FMOC-4'-BROMO-L-PHE;FMOC-P-BROMO-L-PHE-OH;CHEMBL1411271

Canonical SMILES

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

Isomeric SMILES

C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)N[C@@H](CC4=CC=C(C=C4)Br)C(=O)O
Method of Synthesis or Extraction
Fmoc-L-4-Bromophenylalanine can be synthesized using various methods, including the Fmoc-based solid-phase peptide synthesis (SPPS) and solution-phase peptide synthesis. The Fmoc-based SPPS is the most commonly used method for the synthesis of peptides and proteins. It involves the stepwise addition of protected amino acids to a growing peptide chain anchored to a solid support. The efficiency and yield of the Fmoc-based SPPS depend on several factors, including the quality of the reagents, the reaction conditions, and the length and complexity of the peptide sequence. The environmental and safety considerations of the Fmoc-based SPPS include the use of hazardous chemicals, such as organic solvents and acids, and the generation of waste products.
Chemical Structure and Biological Activity
Fmoc-L-4-Bromophenylalanine has a chemical structure that consists of a phenylalanine residue with a bromine atom attached to the para position of the phenyl ring and an Fmoc (9-fluorenylmethoxycarbonyl) protecting group attached to the amino group. The bromine atom enhances the hydrophobicity and electron density of the phenyl ring, which can affect the biological activity of the molecule. Fmoc-L-4-Bromophenylalanine has been shown to exhibit bioactivity and potency against various biological targets, including enzymes, receptors, and ion channels. The mechanism of action of Fmoc-L-4-Bromophenylalanine involves the binding of the molecule to the target protein, which can lead to the inhibition or activation of the protein's function.
Biological Effects
Fmoc-L-4-Bromophenylalanine has been shown to have significant effects on cell function and signal transduction. It can modulate the activity of various signaling pathways, including the MAPK/ERK, PI3K/Akt, and NF-κB pathways, which are involved in cell proliferation, differentiation, and survival. Fmoc-L-4-Bromophenylalanine has also been investigated for its potential therapeutic and toxic effects. It has been shown to have anticancer, antimicrobial, and antiviral properties, as well as neuroprotective and anti-inflammatory effects. However, Fmoc-L-4-Bromophenylalanine can also exhibit toxic effects, such as cytotoxicity and genotoxicity, which can limit its clinical applications.
Future Perspectives and Challenges
Despite the significant progress in the study of Fmoc-L-4-Bromophenylalanine, several challenges and limitations remain. One of the main challenges is the limited understanding of the molecular mechanisms underlying the biological activity and toxicity of Fmoc-L-4-Bromophenylalanine. Another challenge is the development of more efficient and sustainable methods for the synthesis and purification of Fmoc-L-4-Bromophenylalanine. Future perspectives in the application of Fmoc-L-4-Bromophenylalanine in scientific research include the development of novel peptide-based drugs and drug delivery systems, as well as the investigation of its potential applications in regenerative medicine and tissue engineering.
Conclusion:
Fmoc-L-4-Bromophenylalanine is a modified amino acid that has significant potential in the field of medicinal chemistry. It has unique chemical properties that make it a valuable tool for the synthesis of peptides and proteins. Fmoc-L-4-Bromophenylalanine exhibits bioactivity and potency against various biological targets and has significant effects on cell function and signal transduction. However, its potential therapeutic and toxic effects need to be further investigated. Fmoc-L-4-Bromophenylalanine has various applications in medical, environmental, and industrial research, and its future perspectives and challenges require further attention.

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