Synthesis of 2-Fluoroacetoacetic Acid and 4-Fluoro-3-hydroxy­butyric Acid

Synthesis ◽  
2019 ◽  
Vol 51 (11) ◽  
pp. 2351-2358 ◽  
Author(s):  
Stephanie Mattingly ◽  
Frank Wuest ◽  
Ralf Schirrmacher
Keyword(s):  
Ring Opening ◽  
Emission Tomography ◽  
Hydroxybutyric Acid ◽  
Acetoacetic Acid ◽  
Cellular Energy ◽  
Electrophilic Fluorination ◽  
Positron Emission ◽  
Derivatives Of ◽  
Acid Labile ◽  
Base Structure

The butyric acid scaffold is the base structure of several human metabolites that serve diverse and prominent biochemical roles including as oxidative sources of cellular energy and as substrates for biosynthesis. Derivatization of metabolites through incorporation of fluorine often alters bioactivity and can facilitate detection and analysis by nuclear magnetic resonance or positron emission tomography depending upon the fluorine isotope employed. We describe the synthesis of two new fluorinated butyric acids (and three related esters) that are derivatives of the metabolites acetoacetic acid and 3-hydroxybutyric acid. 4-Fluoro-3-hydroxybutyric acid is prepared from epoxy ester precursors via ring opening by triethylamine trihydrofluoride. 2-Fluoroacetoacetic acid is prepared by electrophilic fluorination of an acid-labile β-keto ester. The gradual pH-dependent decarboxylation of 2-fluoroacetoacetic acid is investigated by 19F NMR spectroscopy.

Synthesis and Binding Affinity of Fluorine Containing NG-acyl and -sulfonyl BIBP3226 Derivatives: Ligands for the NPY Y1 Receptor

2016 ◽  
Vol 69 (7) ◽  
pp. 746
Author(s):  
Nigel A. Lengkeek ◽  
Maxine P. Roberts ◽  
Lei Zhang ◽  
I-Chieh J. Lee ◽  
Christopher J. R. Fookes ◽  
...  
Keyword(s):  
Binding Affinity ◽  
Emission Tomography ◽  
Tumour Imaging ◽  
Y1 Receptor ◽  
Important Amino Acid ◽  
Positron Emission ◽  
Npy Receptor ◽  
Almost All ◽  
Derivatives Of ◽  
Pet Radiopharmaceuticals

The neuropeptide Y (NPY) receptors are abundant in a range of tumours hence are a molecular target for tumour imaging and therapy, particularly by the use of radiolabelled molecules. NG-Substituted derivatives of the NPY receptor antagonist, BIBP3226, were prepared aiming to improve its current usability and to incorporate a positron-emitting radioisotope for development in positron emission tomography (PET) radiopharmaceuticals. The BIBP3226 derivatives were prepared in seven steps while retaining the critically important amino acid chirality. The acyl derivative retained acceptable ligand binding, however the sulfonyl derivatives lost almost all binding affinity.

Stereospecific radiosynthesis of 3-fluoro amino acids: access to enantiomerically pure radioligands for positron emission tomography

2018 ◽  
Vol 16 (13) ◽  
pp. 2219-2224 ◽  
Author(s):  
Santosh R. Alluri ◽  
Patrick J. Riss
Keyword(s):  
Amino Acids ◽  
Positron Emission Tomography ◽  
Ring Opening ◽  
Emission Tomography ◽  
Enantiomerically Pure ◽  
Positron Emission ◽  
Ring Opening Reaction

A variety of substituted non-racemic aziridine-2-carboxylates equivalent to amino acids were prepared and subjected to ring opening reaction by [18F/19F]fluoride.

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