We describe a new method for the asymmetric synthesis of [(18)F]fluorinated aromatic alpha-amino acids (FAA) under phase transfer conditions using achiral glycine derivative NiPBPGly and (S)-NOBIN as a novel substrate/catalyst pair. The key alkylation step proceeds under mild conditions. Substituted [(18)F]fluorobenzylbromides were prepared using nucleophilic [(18)F]fluoride and were used as alkylation agents. Two important FAA, 2-[(18)F]fluoro-L-tyrosine (2-FTYR) and 6-[(18)F]fluoro-L-3,4-dihydroxyphenylalanine (6-FDOPA), were synthesized with an ee of 92 and 96%, respectively. The total synthesis time was 110-120 min and radiochemical yields (d.c.) were 25+/-6% for 2-FTYR and 16+/-5% for 6-FDOPA.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1016/j.nucmedbio.2003.12.010 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Synthesis and Antifungal Activity of Fmoc-Protected 1,2,4-Triazolyl-α-Amino Acids and Their Dipeptides Against Species.
Biomolecules
January 2025
Institute of Biostructures and Bioimaging, Italian National Council for Research (IBB-CNR), Area di Ricerca Site and Headquarters, Via Pietro Castellino 111, 80131 Naples, Italy.
In recent years, fungal infections have emerged as a significant health concern across veterinary species, especially in livestock such as cattle, where fungal diseases can result in considerable economic losses, as well as in humans. In particular, species, notably and , are opportunistic pathogens that pose a threat to both animals and humans. This study focuses on the synthesis and antifungal evaluation of novel 9-fluorenylmethoxycarbonyl (Fmoc)-protected 1,2,4-triazolyl-α-amino acids and their dipeptides, designed to combat fungal pathogens.
View Article and Find Full Text PDFThe Petasis Reaction: Applications and Organic Synthesis-A Comprehensive Review.
Top Curr Chem (Cham)
January 2025
Department of Chemistry, Yashavantrao Chavan Institute of Science, Lead College, Karmaveer Bhaurao Patil University, Satara, Maharashtra, 415001, India.
The Petasis reaction has introduced significant advancements through the use of various catalysts, solvents, methodologies, and substrates in diverse areas of chemistry, including medicinal, organic, combinatorial, biochemical, and heterocyclic chemistry. It is a prominent method for synthesizing compounds such as α-amino acids, β-amino alcohols, Aza-beta-lactams, alkylaminophenols, α-arylglycines, 2H-chromenes, aminophenols, and hydrazide alcohols. With the increasing demand for medicines, drugs, industrial products, insecticides, and pesticides, the Petasis reaction has become an indispensable and versatile tool.
View Article and Find Full Text PDFQuantum chemical study of molecular properties of small branched-chain amino acids in water.
Amino Acids
January 2025
Faculty of Natural Sciences, University of SS Cyril and Methodius, 91701, Trnava, Slovakia.
Four aliphatic amino acids-α-aminobutyric acid (AABA), β-aminobutyric acid (BABA), α-aminoisobutyric acid (AAIBA) and β-aminoisobutyric acid (BAIBA) were investigated in water as a solvent by two quantum chemical methods. B3LYP hybrid version of DFT was used for geometry optimization and a full vibrational analysis of neutral molecules, their cations and anions in the canonical and zwitterionic forms (6 forms for each species). Ab initio DLPNO-CCSD(T) method was applied in the geometry pre-optimized by B3LYP.
View Article and Find Full Text PDFCopper-Catalyzed Successive Radical Reactions of Glycine Derivatives.
Org Lett
January 2025
Gansu International Scientific and Technological Cooperation Base of Water-Retention Chemical Functional Materials, Key Laboratory of Eco-Environment-Related Polymer Materials Ministry of Education, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, China.
Here, we present a three-component successive radical addition strategy for the preparation of complex noncanonical α-amino acids from easily available glycine derivatives, alkenes, and aryl sulfonium salts via a copper-catalyzed photoredox-neutral catalytic cycle. The utility of this method is further demonstrated by its application in late-stage site-selective modifications of glycine residues in short peptides. It is worth noting that only 1 mol % copper catalyst is required in this reaction, demonstrating high catalytic efficiency.
View Article and Find Full Text PDFDual Photoredox and Copper-Catalyzed Asymmetric Remote C(sp)-H Alkylation of Hydroxamic Acid Derivatives with Glycine Derivatives.
J Org Chem
January 2025
Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Dual photoredox and copper-catalyzed remote asymmetric C(sp)-H alkylation of hydroxamic acid derivatives with glycine derivatives via a 1,5-hydrogen transfer (1,5-HAT) process has been realized. The reaction was characterized by redox-neutral and mild conditions, good yields, excellent enantioselectivity, and broad substrate scope. This protocol provides a straightforward and efficient strategy to prepare highly valuable enantioenriched noncanonical α-amino acids.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!