ChemInform Abstract: Fluorine-18 Labeled Amino Acids for Oncologic Imaging with Positron Emission Tomography

ChemInform ◽  
2013 ◽  
Vol 44 (41) ◽  
pp. no-no
Author(s):  
Chaofeng Huang ◽  
Jonathan McConathy
Keyword(s):  
Amino Acids ◽  
Positron Emission Tomography ◽  
Emission Tomography ◽  
Oncologic Imaging ◽  
Positron Emission

scholarly journals Aldehyde-Catalyzed Carboxylate Exchange in a-Amino Acids with Isotopically Labeled CO2

2021 ◽  
Author(s):  
Odey Bsharat ◽  
Michael Doyle ◽  
Maxime Munch ◽  
Braeden Mair ◽  
Christopher Cooze ◽  
...  
Keyword(s):  
Amino Acids ◽  
Positron Emission Tomography ◽  
Quantitative Proteomics ◽  
Early Stage ◽  
Building Blocks ◽  
Emission Tomography ◽  
Positron Emission ◽  
Natural Variants ◽  
Label Incorporation ◽  
Essential Chemical

a-Amino acids are among the essential chemical building blocks of life. These structures are embedded in many small molecule pharmaceuticals and are the primary components of peptide-based therapeutics and biologics. Isotopically labeled a-amino acids and their derivatives have widespread use in structural and mechanistic biochemistry, quantitative proteomics, absorption distribution metabolism and excretion (ADME) profiling, and as imaging agents in positron emission tomography (PET) techniques. The preparation of carbon-labeled a-amino acids remains difficult and time consuming, with established methods involving label incorporation at an early stage of synthesis. This explains the high cost and scarcity of C-labeled products and presents a major challenge in 11C applications (11C t1/2 = 20 min). Here we report that simple aldehydes catalyze the isotopic carboxylate exchange of native a-amino acids with *CO2 (* = 14, 13, 11). Proteinogenic a-amino acids and many non-natural variants containing diverse functional groups undergo labeling. The reaction likely proceeds via the trapping of *CO2 by imine-carboxylate intermediates to generate aminomalonates that are prone to monodecarboxylation. Tempering catalyst electrophilicity was key to preventing irreversible aldehyde consumption. The pre-generation of the imine carboxylate intermediate allows for the rapid and late-stage 11C-radiolabeling of a-amino acids in the presence of 11CO2.

Inhibition ofL-{18F}fluorodopa uptake into human brain by amino acids demonstrated by positron emission tomography

1986 ◽  
Vol 20 (2) ◽  
pp. 258-262 ◽  
Author(s):  
K. L. Leenders ◽  
W. H. Poewe ◽  
A. J. Palmer ◽  
D. P. Brenton ◽  
R. S. J. Frackowiak
Keyword(s):  
Amino Acids ◽  
Positron Emission Tomography ◽  
Human Brain ◽  
Emission Tomography ◽  
Positron Emission

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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