Fluorinated phenylalanines: synthesis and pharmaceutical applications

Beilstein Journal of Organic Chemistry
Laila Fathy Awad, Mohammed Salah Ayoup

Abstract

Recent advances in the chemistry of peptides containing fluorinated phenylalanines (Phe) represents a hot topic in drug research over the last few decades. ᴅ- or ʟ-fluorinated phenylalanines have had considerable industrial and pharmaceutical applications and they have been expanded also to play an important role as potential enzyme inhibitors as well as therapeutic agents and topography imaging of tumor ecosystems using PET. Incorporation of fluorinated aromatic amino acids into proteins increases their catabolic stability especially in therapeutic proteins and peptide-based vaccines. This review seeks to summarize the different synthetic approaches in the literature to prepare ᴅ- or ʟ-fluorinated phenylalanines and their pharmaceutical applications with a focus on published synthetic methods that introduce fluorine into the phenyl, the β-carbon or the α-carbon of ᴅ-or ʟ-phenylalanines.

References

Apr 1, 1992·International Journal of Radiation Applications and Instrumentation. Part B, Nuclear Medicine and Biology·K IshiwataY Mishima
Jan 1, 1991·International Journal of Radiation Applications and Instrumentation. Part B, Nuclear Medicine and Biology·K IshiwataY Mishima
Jan 1, 1991·International Journal of Radiation Applications and Instrumentation. Part A, Applied Radiation and Isotopes·K IshiwataY Mishima
Apr 1, 1998·Protein Science : a Publication of the Protein Society·R Furter
Feb 24, 2001·Bioorganic & Medicinal Chemistry Letters·F FiroozniaA Y Jeng
Jul 18, 2001·Journal of the American Chemical Society·B BilgiçerK Kumar
Oct 25, 2001·The Journal of Organic Chemistry·Franklin A. DavisDonald D. Titus
Jun 6, 2003·Medicinal Research Reviews·Rosario Herranz
Nov 10, 2004·Clinical Cancer Research : an Official Journal of the American Association for Cancer Research·Ekaterina S DoubrovinaRichard J O'Reilly
Feb 1, 2006·Chemical Communications : Chem Comm·Hai DengMayca Onega
Feb 25, 2006·The Journal of Organic Chemistry·Lavinia PanellaAdriaan J Minnaard
Dec 7, 2006·Journal of the American Chemical Society·Hsien-Po ChiuRichard P Cheng
Jun 26, 2007·Bioorganic & Medicinal Chemistry Letters·Scott B HoytWilliam H Parsons
Jun 27, 2007·British Journal of Pharmacology·E A HarperS B Kalindjian
Sep 25, 2007·Bioorganic & Medicinal Chemistry Letters·Scott B HoytWilliam H Parsons
Nov 13, 2007·Current Opinion in Pharmacology·Marc J BernaRobert T Jensen
Dec 26, 2007·European Journal of Pharmacology·Elaine A HarperS Barrett Kalindjian
Jan 17, 2008·Chemical Society Reviews·Sophie PurserVéronique Gouverneur
Dec 11, 2008·Journal of the American Chemical Society·Hong ZhengJianmin Gao
Dec 17, 2008·PloS One·Marta Gómez-NuñezDavid A Scheinberg
Oct 10, 2009·Bioorganic & Medicinal Chemistry Letters·Marna PippelMichael H Rabinowitz
Nov 27, 2009·The Journal of Organic Chemistry·Andrew J RossRichard F W Jackson
May 1, 2010·Molecular BioSystems·Nediljko BudisaBirgit Wiltschi
May 27, 2010·Beilstein Journal of Organic Chemistry·Shijie YeBeate Koksch
Nov 23, 2010·Organic & Biomolecular Chemistry·Johnny Castillo MeleánHeinz H Coenen
Mar 3, 2011·Organic & Biomolecular Chemistry·Jing LiuNeelakandha S Mani
Nov 16, 2011·Methods in Molecular Biology·Birgit Wiltschi

❮ Previous
Next ❯

Citations

Nov 13, 2020·Journal of Molecular Graphics & Modelling·Belén HernándezMahmoud Ghomi
Oct 10, 2021·Applied Microbiology and Biotechnology·Xinkuan Cheng, Long Ma

❮ Previous
Next ❯

Methods Mentioned

BETA
NMR
imaging technique

Software Mentioned

Selectfluor
DAST
Selectflour
XtalFluor

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.