Fmoc-2-fluoro-D-phenylalanine Bioactive Reagents Fmoc-2-fluoro-D-phenylalanine is a modified amino acid that has gained significant attention in the field of medicinal chemistry due to its unique properties. It is a fluorinated derivative of phenylalanine, an essential amino acid that plays a crucial role in protein synthesis. Fmoc-2-fluoro-D-phenylalanine has been extensively studied for its potential therapeutic applications, as well as its role in environmental and industrial research. This paper aims to provide a comprehensive review of Fmoc-2-fluoro-D-phenylalanine, including its method of synthesis, chemical structure, biological activity, effects on cell function and signal transduction, applications in medical, environmental, and industrial research, and future perspectives and challenges.
405.4 g/mol
$ $99 In stock
Formulation: 405.4 g/mol
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Usage:
Fmoc-2-fluoro-D-phenylalanine - 198545-46-9

Fmoc-2-fluoro-D-phenylalanine

The product is for non-human research only. Not for therapeutic or veterinary use.

Catalog Number: BT-251193

CAS Number: 198545-46-9

Molecular Formula: C24H20FNO4

Molecular Weight: 405.4 g/mol

Purity: ≥ 97%

Inventory: In Stock

Size SKU Price
250mg bt-251193-250mg $306.15
1g bt-251193-1g $699.69
5g bt-251193-5g $2,974.00
10g bt-251193-10g $5,341.23
25g bt-251193-25g $12,798.31
100g bt-251193-100g $33,337.85

CAS Number 198545-46-9
Product Name Fmoc-2-fluoro-D-phenylalanine
Molecular Formula C24H20FNO4
Molecular Weight 405.4 g/mol
InChI InChI=1S/C24H20FNO4/c25-21-12-6-1-7-15(21)13-22(23(27)28)26-24(29)30-14-20-18-10-4-2-8-16(18)17-9-3-5-11-19(17)20/h1-12,20,22H,13-14H2,(H,26,29)(H,27,28)/t22-/m1/s1
InChI Key ARHOAMSIDCQWEW-JOCHJYFZSA-N
Isomeric SMILES C1=CC=C(C(=C1)C[C@H](C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)F
IUPAC Name (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-(2-fluorophenyl)propanoic acid
Canonical SMILES C1=CC=C(C(=C1)CC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)F
Description Fmoc-2-fluoro-D-phenylalanine is a modified amino acid that has gained significant attention in the field of medicinal chemistry due to its unique properties. It is a fluorinated derivative of phenylalanine, an essential amino acid that plays a crucial role in protein synthesis. Fmoc-2-fluoro-D-phenylalanine has been extensively studied for its potential therapeutic applications, as well as its role in environmental and industrial research. This paper aims to provide a comprehensive review of Fmoc-2-fluoro-D-phenylalanine, including its method of synthesis, chemical structure, biological activity, effects on cell function and signal transduction, applications in medical, environmental, and industrial research, and future perspectives and challenges.
Method of Synthesis or Extraction Fmoc-2-fluoro-D-phenylalanine can be synthesized using various methods, including the Fmoc-based solid-phase peptide synthesis (SPPS) and the solution-phase synthesis. The Fmoc-based SPPS is the most commonly used method for the synthesis of Fmoc-2-fluoro-D-phenylalanine-containing peptides. This method involves the stepwise addition of Fmoc-2-fluoro-D-phenylalanine to a growing peptide chain, followed by deprotection of the Fmoc group using a base. The efficiency and yield of this method depend on the quality of the starting materials, the reaction conditions, and the purification methods used. The solution-phase synthesis involves the reaction of Fmoc-2-fluoro-D-phenylalanine with other amino acids in a solution, followed by purification using chromatography. This method is less commonly used due to its lower efficiency and yield. Environmental and safety considerations should be taken into account during the synthesis of Fmoc-2-fluoro-D-phenylalanine, as it involves the use of hazardous chemicals and solvents.
Chemical Structure and Biological Activity Fmoc-2-fluoro-D-phenylalanine has a chemical structure similar to that of phenylalanine, with the addition of a fluorine atom at the 2-position of the phenyl ring. This modification enhances the lipophilicity and metabolic stability of the amino acid, making it a promising candidate for drug development. Fmoc-2-fluoro-D-phenylalanine has been shown to exhibit potent biological activity, including inhibition of proteases, antimicrobial activity, and modulation of ion channels. Its mechanism of action and biological targets depend on the specific peptide or protein it is incorporated into.
Biological Effects Fmoc-2-fluoro-D-phenylalanine has been shown to have various effects on cell function and signal transduction. It can modulate the activity of ion channels, leading to changes in membrane potential and calcium signaling. It can also inhibit proteases, leading to the suppression of proteolytic activity and the prevention of protein degradation. Fmoc-2-fluoro-D-phenylalanine has potential therapeutic and toxic effects, depending on the specific peptide or protein it is incorporated into. It has been shown to have anti-inflammatory, analgesic, and anticancer effects, as well as potential toxic effects on the liver and kidneys.
Applications Fmoc-2-fluoro-D-phenylalanine has various applications in medical, environmental, and industrial research. In medical research, it has been used in drug development, particularly in the design of protease inhibitors and ion channel modulators. It has also been studied in clinical trials for its potential therapeutic effects in various diseases, including cancer, inflammation, and pain. In environmental research, Fmoc-2-fluoro-D-phenylalanine has been used to study the effects of fluorinated amino acids on ecosystems and to develop methods for pollution management. In industrial research, it has been used in manufacturing processes to improve product quality and efficiency, with a focus on health and safety considerations.
Future Perspectives and Challenges Despite the promising potential of Fmoc-2-fluoro-D-phenylalanine, there are still limitations in its use and study. One of the main challenges is the lack of understanding of its long-term effects on human health and the environment. There is also a need for more efficient and cost-effective methods for its synthesis and purification. Future trends and prospects in the application of Fmoc-2-fluoro-D-phenylalanine in scientific research include the development of new drug candidates, the study of its effects on the microbiome, and the exploration of its potential in sustainable agriculture.
Conclusion:
Fmoc-2-fluoro-D-phenylalanine is a modified amino acid that has gained significant attention in the field of medicinal chemistry due to its unique properties. It has been extensively studied for its potential therapeutic applications, as well as its role in environmental and industrial research. The method of synthesis, chemical structure, biological activity, effects on cell function and signal transduction, applications, and future perspectives and challenges of Fmoc-2-fluoro-D-phenylalanine have been discussed in this paper. Further research is needed to fully understand the potential of this amino acid and its impact on human health and the environment.
SMILES C1=CC=C(C(=C1)CC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)F
Synonyms Fmoc-2-fluoro-D-phenylalanine;198545-46-9;Fmoc-D-Phe(2-F)-OH;CHEMBL2012790;FMOC-D-2-Fluorophe;(R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(2-fluorophenyl)propanoicacid;FMOC-D-2-FLUOROPHENYLALANINE;AmbotzFAA6330;Fmoc-2-fluoro-D-Phe;AC1OFJ55;47767_ALDRICH;SCHEMBL119553;47767_FLUKA;CTK8C5112;MolPort-001-771-329;(R)-N-FMOC-2-Fluorophenylalanine;ZINC4208792;ANW-74148;BDBM50380071;AKOS015908574;AC-5825;AM83333;RTR-009230;VZ36564;AJ-48907
PubChem Compound Fmoc-2-fluoro-D-phenylalanine
Last Modified May 30 2023