Asymmetric Synthesis of L-[beta-11C]Alanine Using A Glycine Derivative with Two Chiral Handles, (1R,2S,3R)-8-Phenylmenthan-3-yl N-[(1R,2R,5R)-2-Hydroxypinan-3-ylidene]glycinate.

Fasth, Karl-Johan; Antoni, Gunnar; Långström, Bengt; Alberti, G.; Nielsen, M.; Lehmann, Martin; Tokii, Tadashi

doi:10.3891/acta.chem.scand.44-0527

Cited by 8 publications

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“…Other methods to radiolabel alanine has been developed based on chiral glycine or imidazolidinone derivatives giving higher enantiomeric purities as shown in Scheme …”

Section: Pet Tracer Development From An Academic View—endogenous Compmentioning

confidence: 99%

Development of carbon‐11 labelled PET tracers—radiochemical and technological challenges in a historic perspective

Antoni

2015

Labelled Comp Radiopharmac

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The development of positron emission tomography (PET) from being an exclusive and expensive research tool at major research institutes to a clinically useful modality found at most major hospitals around the world is largely dependent on radiochemistry and synthesis technology achievements by a few pioneer researchers starting their PET careers 40 to 50 years ago. Especially, the introduction of [(11) C]methyl iodide resulted in a quantum jump in the history of PET tracer development enabling the smooth labelling of a multitude of useful tracers. A more recent and still challenging methodological improvement is transition metal mediated (11) C-carbonylations, having a large synthetic potential that has, however, not yet been realized in the clinical setting. This mini-review focuses on the history of carbon-11 radiochemistry and related technology developments and the role this played in PET tracer developments, especially emphasizing radiolabelling of endogenous compounds. A few examples will be presented of how the use of radiolabelled endogenous substances have provided fundamental information of in vivo biochemistry using the concept of position-specific labelling in different positions in the same molecule.

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“…Other methods to radiolabel alanine has been developed based on chiral glycine or imidazolidinone derivatives giving higher enantiomeric purities as shown in Scheme …”

Section: Pet Tracer Development From An Academic View—endogenous Compmentioning

confidence: 99%

Development of carbon‐11 labelled PET tracers—radiochemical and technological challenges in a historic perspective

Antoni

2015

Labelled Comp Radiopharmac

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“…Labeling in the 3‐position (or β in the case of aromatic amino acids) can be achieved by alkylation using aliphatic or aromatic alkyl halides . This approach has also been applied in asymmetric syntheses of aliphatic [ 11 C]amino acids using different glycine derivatives such as [(+)‐2‐hydroxypinanyl‐3‐idene]glycine tert ‐butyl ester, the nickel complex of the Schiff base of (S)‐ O ‐[( N ‐benzylpropyl)amino]benzophenone and glycine . The most promising method, which gives nearly enantiomerically pure [ 11 C]amino acids, used an imidazolidinone derivative (Scheme ) .…”

Section: Preparation and Labeling Of Endogenous Compoundsmentioning

confidence: 99%

Endogenous compounds labeled with radionuclides of short half‐life—some perspectives

Långström¹,

Karimi

Watanabe

2013

Labelled Comp Radiopharmac

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In the article, the strategy and synthesis of some endogenous compounds labeled mainly with (11) C are presented. There are some examples illustrating how endogenous labeled compounds in connection with positron emission tomography have unique properties to describe various biological processes, and a few examples of the use of tracers labeled with (13) N and (15) O are also discussed. Labeled endogenous compounds may be an important asset to describe the conditions and the status of biological systems and might therefore be a key for the future search of individualized medicine.

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Radiochemistry with Carbon‐11

Thompson

Kealey

Sephton

et al. 2020

Handbook of Radiopharmaceuticals

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Asymmetric Synthesis of L-[beta-11C]Alanine Using A Glycine Derivative with Two Chiral Handles, (1R,2S,3R)-8-Phenylmenthan-3-yl N-[(1R,2R,5R)-2-Hydroxypinan-3-ylidene]glycinate.

Cited by 8 publications

References 0 publications

Development of carbon‐11 labelled PET tracers—radiochemical and technological challenges in a historic perspective

Development of carbon‐11 labelled PET tracers—radiochemical and technological challenges in a historic perspective

Endogenous compounds labeled with radionuclides of short half‐life—some perspectives

Radiochemistry with Carbon‐11

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