☆ 4.8 Review

Development and application of decatungstate catalyzed C-H 18F- and 19F-fluorination, fluoroalkylation and beyond

CHEMICAL SCIENCE (2023)

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Article Chemistry, Organic

Decatungstate-Catalyzed C(sp3)-H Alkylation of a Val Residue Proximal to the N-Terminus Controlled by an Electrostatic Interaction

Jizhou Song et al.

Summary: The decatungstate photocatalyst [W10O32](4-) efficiently promotes the C-(sp(3))-Halkylation reaction between the trifluoroacetic acid salt of valine methyl ester (H-Val-OMe center dot TFA) and electron-deficient alkenes under UV irradiation. The electrostatic interaction between the cationic ammonium group (+NH3) and anionic [W10O32](4-) plays a crucial role in this reaction. The study also demonstrates the successful introduction of an alkyne moiety into valine and the subsequent copper-catalyzed azide-alkyne cycloaddition (CuAAC).

ORGANIC LETTERS (2023)

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Review Chemistry, Multidisciplinary

Photocatalytic Late-Stage C-H Functionalization

Peter Bellotti et al.

Summary: The emergence of modern photocatalysis has revolutionized late-stage C-H functionalization, offering unprecedented regio- and chemoselectivities. This Review focuses on the strategies of small-molecule drugs, agrochemicals, and natural products, highlighting the main mechanistic scenarios and comparing established ionic chemistry and photocatalyzed radical-based manifolds. The authors aim to provide a comprehensive overview of the current state-of-the-art and address the challenges and future directions in this field.

CHEMICAL REVIEWS (2023)

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Article Multidisciplinary Sciences

Functional-group translocation of cyano groups by reversible C-H sampling

Ken Chen et al.

Summary: In this study, a photocatalytic reversible C-H sampling reaction was developed to achieve the translocation of cyano groups in nitriles. This reaction enables the direct exchange between a cyano group and an unactivated C-H bond, offering a selective and valuable method for the synthesis of unconventional C-H derivatives and building blocks of bioactive molecules.

NATURE (2023)

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Review Chemistry, Multidisciplinary

Alkoxy Radicals See the Light: New Paradigms of Photochemical Synthesis

Liang Chang et al.

Summary: This review comprehensively summarizes the recent progress in alkoxy radical-mediated transformations under visible light irradiation. The mechanisms of alkoxy radical generation and their impact on synthetic utilizations are discussed. The catalytic generation of alkoxy radicals from abundant alcohols is still in the early stage, but holds great potential.

CHEMICAL REVIEWS (2022)

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Review Chemistry, Multidisciplinary

Metallaphotoredox: The Merger of Photoredox and Transition Metal Catalysis

Amy Y. Chan et al.

Summary: The merger of photoredox catalysis with transition metal catalysis, known as metallaphotoredox catalysis, has become an important part of synthetic methodology. It combines the bond formation capability of transition metal catalysis with the utility of photoinduced electron and energy transfer processes. Photocatalytic substrate activation allows the involvement of simple starting materials in metal-mediated bond-forming processes, while electron or energy transfer with organometallic intermediates provides a complementary activation mode to traditional catalytic platforms.

CHEMICAL REVIEWS (2022)

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Review Chemistry, Multidisciplinary

Photocatalysis in the Life Science Industry

Lisa Candish et al.

Summary: This Review summarizes the contributions to the field of photocatalysis from the life science industry, including the development of synthetic methodologies and strategic applications in chemical synthesis. The state-of-the-art in photoreactor technology and the effective upscaling of photocatalytic reactions are also discussed.

CHEMICAL REVIEWS (2022)

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Article Chemistry, Organic

Decatungstate Catalyzed Synthesis of Trifluoromethylthioesters from Aldehydes via a Radical Process

Zhegao Ye et al.

Summary: A mild and general method for trifluoromethylthiolation of aldehydes using N-trifluoromethylthiosaccharin and sodium decatungstate as the photocatalyst has been reported. Electron-rich aldehydes show better reactivity, while good selectivity is observed for the trifluoromethylthiolation of aldehydic C-H bonds. Preliminary mechanistic studies suggest a free radical process is involved.

JOURNAL OF ORGANIC CHEMISTRY (2022)

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Review Chemistry, Multidisciplinary

A Perspective on Late-Stage Aromatic C-H Bond Functionalization

Li Zhang et al.

Summary: Aromatic C-H late-stage functionalization poses challenges in terms of reactivity, selectivity, and substrate scope, but also shows potential for development. It is necessary to address current challenges and explore new strategies and directions for growth.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

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Article Chemistry, Physical

Control of Site-Selectivity in Hydrogen Atom Transfer by Electrostatic Interaction: Proximal-Selective C(sp3)-H Alkylation of 2-Methylanilinium Salts Using a Decatungstate Photocatalyst

Jialin Zeng et al.

Summary: A new method was developed for site-selective C(sp(3))-H alkylation of 2-methylanilinium salts using radical intermediates. Mechanistic studies confirmed the interaction between the anionic decatungstate photocatalyst ([W10O32](4-)) and the substrate's ammonium group, leading to successful formation of the desired product.

ACS CATALYSIS (2022)

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Article Radiology, Nuclear Medicine & Medical Imaging

Initial evaluation of [18F]-FACBC for PET imaging of multiple myeloma

Volker Morath et al.

Summary: This study compares the tumor uptake of two amino acid analogs in a multiple myeloma model and demonstrates the feasibility of PET imaging with one of the analogs in a multiple myeloma patient. Further investigation shows the potential use of this amino acid analog for imaging multiple myeloma.

EJNMMI RESEARCH (2022)

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Review Chemistry, Multidisciplinary

Direct Photocatalyzed Hydrogen Atom Transfer (HAT) for Aliphatic C-H Bonds Elaboration

Luca Capaldo et al.

Summary: Direct photocatalyzed hydrogen atom transfer (d-HAT) is a preferred method for the synthesis of aliphatic C-H bonds in organic compounds. Selective C-H bond elaboration can be achieved by choosing suitable hydrogen abstractors and reaction additives. This review provides a comprehensive survey of the synthetic applications of photocatalyzed d-HAT.

CHEMICAL REVIEWS (2022)

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Review Chemistry, Multidisciplinary

Technological Innovations in Photochemistry for Organic Synthesis: Flow Chemistry, High-Throughput Experimentation, Scale-up, and Photoelectrochemistry

Laura Buglioni et al.

Summary: This paper provides a comprehensive overview of the exciting technological advances in the field of photoinduced chemical transformations, including flow chemistry, high-throughput experimentation, reactor design and scale-up, and the combination of photo- and electro-chemistry.

CHEMICAL REVIEWS (2022)

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Review Chemistry, Organic

Noncovalent interactions: A brief account of a long history

Hans-Joerg Schneider

Summary: This article outlines the history of noncovalent interactions, starting with early interpretations of crystal symmetry, followed by the rapid development of coordination chemistry and fundamental analyses in the last century. It attempts to provide practicing scientists who use noncovalent interactions with a historical background of the field, giving credit to often forgotten predecessors. A separate section highlights how instrumentation in the 20th century provided a solid foundation for the exploration of noncovalent interactions. Selected examples demonstrate early and accurate calculations of some noncovalent energies. With the rise of supramolecular chemistry, noncovalent interactions have become a mainstream field of science, allowing further understanding of the nature and strength of these seemingly weak forces. Interactions between molecules in biological systems also received early attention.

JOURNAL OF PHYSICAL ORGANIC CHEMISTRY (2022)

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Review Chemistry, Multidisciplinary

A Fruitful Decade of Organofluorine Chemistry: New Reagents and Reactions

Feng-Ling Qing et al.

Summary: The development of synthetic methods for introducing fluorine atoms and fluoroalkyl groups into organic molecules has received increased attention. Synthetic organic chemists have made significant contributions in the field of organofluorine chemistry and the newly developed methods are typically safer and more effective than traditional methods.

CCS CHEMISTRY (2022)

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Article Chemistry, Multidisciplinary

Selective Axial-to-Equatorial Epimerization of Carbohydrates

Hayden M. Carder et al.

Summary: Radical-mediated transformations are powerful methods for synthesizing rare and unnatural sugars. This study presents a radical-mediated axial-to-equatorial alcohol epimerization method that can transform abundant sugars into rare isomers with predictable and selective outcomes.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

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Article Chemistry, Multidisciplinary

Strategies That Utilize Ion Pairing Interactions to Exert Selectivity Control in the Functionalization of C-H Bonds

James E. Gillespie et al.

Summary: Ion-pairing interactions can be used to control selectivity in chemical reactions, especially in C-H bond functionalization processes. This emerging field is of great interest to chemists in both industry and academia.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

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Stereochemical editing logic powered by the epimerization of unactivated tertiary stereocenters

Yu-An Zhang et al.

SCIENCE (2022)

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Review Chemistry, Multidisciplinary

Fluorinated Rings: Conformation and Application

Rajarshi Mondal et al.

Summary: This article discusses the impact of fluorine substitution on the relative orientation of C-F bonds in organic molecules, as well as the conformational behavior and stability of fluorinated aliphatic carbo- and heterocyclic systems. The contribution of charge-dipole, dipole-dipole, and hyperconjugative interactions to the stability of fluorinated alicyclic systems is detailed, alongside the presentation of the most recent applications.

CHEMISTRY-A EUROPEAN JOURNAL (2021)

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Article Chemistry, Multidisciplinary

Decatungstate as a direct hydrogen atom transfer photocatalyst for synthesis of trifluromethylthioesters from aldehydes

Xiaochen Wang et al.

Summary: A versatile and mild protocol for trifluoromethylthiolation reactions of aldehydes has been developed, catalyzed by a decatungstate hydrogen atom transfer photocatalyst under redox-neutral conditions. The protocol is highly selective, operationally simple, and compatible with a wide array of sensitive functional groups, making it convenient for late-stage functionalization of bioactive molecules in drug discovery.

CHINESE CHEMICAL LETTERS (2021)

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Article Chemistry, Organic

Decatungstate as Direct Hydrogen Atom Transfer Photocatalyst for SOMOphilic Alkynylation

Luca Capaldo et al.

Summary: A versatile approach for alkynylation of various aliphatic hydrogen donors including alkanes was achieved using tetrabutylammonium decatungstate as a photocatalyst. The reaction mechanism involved generating organoradicals from C-H/Si-H bonds followed by SOMOphilic alkynylation to form internal alkynes. The impact of different radicofugal groups on the reaction outcome was evaluated through experimental and computational methods.

ORGANIC LETTERS (2021)

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Article Chemistry, Multidisciplinary

Decatungstate-Mediated C(sp3)-H Heteroarylation via Radical-Polar Crossover in Batch and Flow

Ting Wan et al.

Summary: The study developed an important photocatalytic strategy for the regioselective C(sp(3))-H functionalization of organic molecules, demonstrating high functional group tolerance and scalability, suitable for late-stage functionalization of biologically relevant molecules.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Organic

18F-Fluorination: Challenge and Opportunity for Organic Chemists

Riya Halder et al.

Summary: F-18-fluorination is an important and rapidly growing field in organic synthesis that has attracted significant attention from chemists. This manuscript presents a biased perspective on recent advances in the field, with a focus on the author's own chemistry, and discusses challenges for the development of new chemistry with potential impact on imaging. The aim is to provide a useful guide for chemists to develop reliable reaction chemistry suitable for radiofluorination to make a real impact on human health.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

Photocatalytic C-H Trifluoromethylthiolation by the Decatungstate Anion

Tobias E. Schirmer et al.

Summary: A broadly applicable method for trifluorome-thylthiolation of various types of C-H bonds using decatungstate anion as the sole catalyst has been developed, achieving good regioselectivities in 40 examples, including natural product derivatization. Additionally, SCF3-drug analogues were synthesized by subsequent functionalization of the SCF3 products, highlighting the importance of this photocatalyzed C-H functionalization.

ORGANIC LETTERS (2021)

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Review Chemistry, Multidisciplinary

Late-stage C-H functionalization offers new opportunities in drug discovery

Lucas Guillemard et al.

Summary: In the past decade, the introduction of late-stage functionalization methodologies has significantly advanced the landscape of molecular synthesis. Particularly, C-H functionalization approaches have led to improvements in resource economy and new strategies for drug discovery. However, challenges and limitations in current LSF methods indicate the need for future improvements and development of new approaches.

NATURE REVIEWS CHEMISTRY (2021)

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Article Multidisciplinary Sciences

Contemporary synthetic strategies in organofluorine chemistry

Robert Britton et al.

Summary: Fluorinated molecules have various applications, with fluorination and fluoroalkylation being the main strategies for constructing carbon-fluorine and fluorinated carbon-carbon bonds. Rapid growth in fluorination and fluoroalkylation methods has been witnessed in the past two decades due to the development of new reagents and catalysts, and further landmark achievements are expected in everyday applications as organofluorine compounds are increasingly used.

NATURE REVIEWS METHODS PRIMERS (2021)

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Article Chemistry, Multidisciplinary

Nickel/Photo-Cocatalyzed Asymmetric Acyl-Carbamoylation of Alkenes

Pei Fan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Multidisciplinary Sciences

Photoinduced site-selective alkenylation of alkanes and aldehydes with aryl alkenes

Hui Cao et al.

NATURE COMMUNICATIONS (2020)

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Article Chemistry, Physical

Light-Mediated Asymmetric Aliphatic C-H Alkylation with Hydrogen Atom Transfer Catalyst and Chiral Phosphoric Acid

Zhen-Yao Dai et al.

ACS CATALYSIS (2020)

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The merger of decatungstate and copper catalysis to enable aliphatic C(sp3)-H trifluoromethylation

Patrick J. Sarver et al.

NATURE CHEMISTRY (2020)

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Article Chemistry, Organic

Acylation of Aryl Halides and α-Bromo Acetates with Aldehydes Enabled by Nickel/TBADT Cocatalysis

Pei Fan et al.

ORGANIC LETTERS (2020)

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C(sp3)-H functionalizations of light hydrocarbons using decatungstate photocatalysis in flow

Gabriele Laudadio et al.

SCIENCE (2020)

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Direct C-H Arylation of Aldehydes by Merging Photocatalyzed Hydrogen Atom Transfer with Palladium Catalysis

Lu Wang et al.

ACS CATALYSIS (2020)

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Light-Mediated Difluoromethylthiolation of Aldehydes with a Hydrogen Atom Transfer Photocatalyst

Jianyang Dong et al.

ORGANIC LETTERS (2020)

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Photoinduced Decatungstate-Catalyzed C-H Functionalization

Xiaoya Yuan et al.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2020)

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Formyl-selective deuteration of aldehydes with D2O via synergistic organic and photoredox catalysis

Jianyang Dong et al.

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Recent progress of transition metal-catalysed regioselective C-H transformations based on noncovalent interactions

Yoichiro Kuninobu et al.

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The Fluorination of C-H Bonds: Developments and Perspectives

Robert Szpera et al.

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18F-Branched-Chain Amino Acids: Structure-Activity Relationships and PET Imaging Potential

Matthew B. Nodwell et al.

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The L-Type Amino Acid Transporter LAT1An Emerging Target in Cancer

Pascal Hafliger et al.

INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES (2019)

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Electrostatic Effects Accelerate Decatungstate-Catalyzed C-H Fluorination Using [18F]- and [19F]NFSI in Small Molecules and Peptide Mimics

Zheliang Yuan et al.

ACS CATALYSIS (2019)

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The importance of synthetic chemistry in the pharmaceutical industry

Kevin R. Campos et al.

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Site-Selective C-H Functionalization by Decatungstate Anion Photocatalysis: Synergistic Control by Polar and Steric Effects Expands the Reaction Scope

Davide Ravelli et al.

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Visible-Light Photocatalysis: Does It Make a Difference in Organic Synthesis?

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David C. Blakemore et al.

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Direct heterobenzylic fluorination, difluorination and trifluoromethylthiolation with dibenzenesulfonamide derivatives

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Applications of Fluorine in Medicinal Chemistry

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Development of a Direct Photocatalytic C-H Fluorination for the Preparative Synthesis of Odanacatib

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Identification of Novel Peptide Ligands for the Cancer-Specific Receptor Mutation EFGRvIII Using a Mixture-Based Synthetic Combinatorial Library

Charlotte Lund Denholt et al.

BIOPOLYMERS (2009)

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Review Chemistry, Multidisciplinary

Decatungstate as an efficient photocatalyst in organic chemistry

Manolis D. Tzirakis et al.

CHEMICAL SOCIETY REVIEWS (2009)

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Article Chemistry, Applied

Tetrabutylammonium Decatungstate (Chemo)selective Photocatalyzed, Radical C-H Functionalization in Amides

Simone Angioni et al.

ADVANCED SYNTHESIS & CATALYSIS (2008)

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Review Chemistry, Multidisciplinary

Synthesis of C-11, F-18, O-15, and N-13 Radiolabels for Positron Emission Tomography

Philip W. Miller et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2008)

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Review Chemistry, Multidisciplinary

Molecular imaging with PET

Simon M. Ametamey et al.

CHEMICAL REVIEWS (2008)

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Review Chemistry, Multidisciplinary

Understanding organofluorine chemistry. An introduction to the C-F bond

David O'Hagan

CHEMICAL SOCIETY REVIEWS (2008)

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Review Chemistry, Multidisciplinary

Fluorine in medicinal chemistry

Sophie Purser et al.

CHEMICAL SOCIETY REVIEWS (2008)

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Review Chemistry, Applied

Fluorination in medicinal chemistry: Methods, strategies, and recent developments

Kenneth L. Kirk

ORGANIC PROCESS RESEARCH & DEVELOPMENT (2008)

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Article Chemistry, Physical

Mechanism of decatungstate photocatalyzed oxygenation of aromatic alcohols Part II. Kinetic isotope effects studies

Ioannis N. Lykakis et al.

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL (2007)

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Article Chemistry, Multidisciplinary

Synthesis and reactivity of [F-18]-N-fluorobenzenesulfonimide

Harriet Teare et al.

CHEMICAL COMMUNICATIONS (2007)

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Article Chemistry, Multidisciplinary

Acylation of electrophilic olefins through decatungstate-photocatalyzed activation of aldehydes

Silvia Esposti et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2007)

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Article Chemistry, Organic

A concise synthesis of (S)-γ-fluoroleucine ethyl ester

C Nadeau et al.

SYNLETT (2006)

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Article Biochemical Research Methods

Synthesis of N-succinimidyl 4-[F-18] fluorobenzoate, an agent for labeling proteins and peptides with F-18

Ganesan Vaidyanathan et al.

NATURE PROTOCOLS (2006)

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Review Oncology

Amino acid transporters ASCT2 and LAT1 in cancer: Partners in crime?

BC Fuchs et al.

SEMINARS IN CANCER BIOLOGY (2005)

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Article Chemistry, Organic

Practical and efficient route to (S)-γ-fluoroleucine

VL Truong et al.

SYNLETT (2005)

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Article Chemistry, Organic

An efficient chemoenzymatic approach to (S)-γ-fluoroleucine ethyl ester

J Limanto et al.

JOURNAL OF ORGANIC CHEMISTRY (2005)

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Article Chemistry, Multidisciplinary

A weak attractive interaction between organic fluorine and an amide group

F Hof et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2004)

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Article Biochemistry & Molecular Biology

NAAG peptidase inhibition reduces locomotor activity and some stereotypes in the PCP model of schizophrenia via group II mGluR

RT Olszewski et al.

JOURNAL OF NEUROCHEMISTRY (2004)

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Article Pharmacology & Pharmacy

Transport of amino acid-related compounds mediated by L-type amino acid transporter 1 (LAT1): Insights into the mechanisms of substrate recognition

H Uchino et al.

MOLECULAR PHARMACOLOGY (2002)

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Article Chemistry, Multidisciplinary

Fluoroaromatic-fluoroaromatic interactions between inhibitors bound in the crystal lattice of human carbonic anhydrase II

CY Kim et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2001)

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Article Multidisciplinary Sciences

Positron emission tomography provides molecular imaging of biological processes

ME Phelps

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA (2000)

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Article Chemistry, Physical

Reactivity of the charge transfer excited state of sodium decatungstate at the nanosecond time scale

I Texier et al.

PHYSICAL CHEMISTRY CHEMICAL PHYSICS (2000)

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