Synthesis of Highly Enantio-Enriched α-Amino Acids by Carboxylation ofN-(α-Lithioalkyl)oxazolidinones

Jeanjean, Fabien; Fournet, Guy; Bars, Didier Le; Goré, J.

doi:10.1002/1099-0690(200004)2000:7<1297::aid-ejoc1297>3.0.co;2-l

Cited by 31 publications

(23 citation statements)

References 26 publications

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“…However, authors did not give data on the performance of this interesting 11 C-labelling approach. 33,34 The syntheses of a-[2-11 C]aminoisobutyric acid and a-(N-methyl)-[2-11 C]aminoisobutyric acid were performed by a Zelinski-Stadnikoff variation 35 of the Strecker a-amino acid synthesis. This proceeded by an addition of methyllithium to [ 11 C]CO 2 to form [ 11 C]acetone that was converted in situ to the corresponding a-[2-11 C]aminoisobutyronitriles in the presence of sodium cyanide and ammonium sulfate.…”

Section: Enzymatic Methods (Route a Figure 1)mentioning

confidence: 99%

“…Instead of using α‐lithioisonitriles, a promising, alternative method was developed to obtain l ‐[1‐ 11 C]methionine in good yield and high enantiomeric excess by using the carboxylation of an enantiopure α‐lithiooxazolidinone prepared by tin–lithium exchange. However, authors did not give data on the performance of this interesting 11 C‐labelling approach …”

Section: C‐labelled Amino Acidsmentioning

confidence: 99%

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Methods for ¹¹C‐ and ¹⁸F‐labelling of amino acids and derivatives for positron emission tomography imaging

Neumaier

Coenen

2013

Labelled Comp Radiopharmac

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The different concepts realized for the synthesis of (11) C- and (18) F-labelled amino acids are summarized. Carbon-11 enables principally authentic radiolabelling of natural occurring amino acids by substituting one of the skeleton carbons by the radionuclide. Fluorine-18 is a foreign element for natural amino acids. Because of its advantageous nuclidic properties for positron emission tomography, however, it becomes increasingly important in molecular imaging, also with amino acid analogues. Especially in the last decade, considerable progress has been made with the radiosynthesis of (18) F-labelled amino acids that are now clinically approved, and thus assure their availability. In contrast, the synthetic possibilities with (11) C-labelled amino acids are more limited because of the short half-life of carbon-11 which also hampers their wide spread use.

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Section: Enzymatic Methods (Route a Figure 1)mentioning

confidence: 99%

Section: C‐labelled Amino Acidsmentioning

confidence: 99%

Methods for ¹¹C‐ and ¹⁸F‐labelling of amino acids and derivatives for positron emission tomography imaging

Neumaier

Coenen

2013

Labelled Comp Radiopharmac

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“…Finally, the chiral auxiliary was removed by a Birch-type reduction to yield the unprotected and entantiomerically pure C-11-labeled AA, which was purified by ion exchange chromatography. In view of the good results, this method has been extended to C-11-labeled L-leucine, L-alanine, and L-homocysteine, accomplished with an overall yield of 13-33 % with 92-95 % ee [45].…”

Section: Carbon-11 Amino Acid Labelingmentioning

confidence: 99%

“…The optimization for the routine preparation of labeled L-[ 11 C]MET has been initiated, however to the best of our knowledge has not been published [45].…”

Section: Carbon-11 Amino Acid Labelingmentioning

confidence: 99%

From Carbon-11-Labeled Amino Acids to Peptides in Positron Emission Tomography: the Synthesis and Clinical Application

et al. 2018

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Radiolabeled amino acids, their derivatives and peptides have a broad scope of application and can be used as receptor ligands, as well as enzyme substrates for many different diseases as radiopharmaceutical tracers. Over the past few decades, the application of molecular imaging techniques such as positron emission tomography (PET) has gained considerable importance and significance in diagnosis in today's advanced health care. Next to that, the availability of cyclotrons and state-of-the-art radiochemistry facilities has progressed the production of imaging agents enabling the preparation of many versatile PET radiotracers. Due to many favorable characteristics of radiolabeled amino acids and peptides, they can be used for tumor staging and monitoring the progress of therapy success, while aromatic amino acids can be employed as PET tracer to study neurological disorders. This review provides a comprehensive overview of radiosynthetic and enzymatic approaches towards carbon-11 amino acids, their analogues and peptides, with focus on stereoselective reactions, and reflects upon their clinical application.

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“…Our choice was oriented towards the ring-opening of 2-tributylstannyloxazolidines in order to avoid the use of hardly storable a-iodoalkyltins, acyltins or a-stannylalcohols which have been previously used for the stereoselective synthesis of chiral a-aminoorganotributyltins [12][13][14][15][16][17]19,20].…”

Section: Introductionmentioning

confidence: 99%

Diastereoselective synthesis of chiral α-aminoorganotributyltins via ring-opening of 2-tributylstannyloxazolidines

Coeffard¹,

Cintrat²,

Grognec³

et al. 2006

Journal of Organometallic Chemistry

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Synthesis of Highly Enantio-Enriched α-Amino Acids by Carboxylation ofN-(α-Lithioalkyl)oxazolidinones

Cited by 31 publications

References 26 publications

Methods for ¹¹C‐ and ¹⁸F‐labelling of amino acids and derivatives for positron emission tomography imaging

Methods for ¹¹C‐ and ¹⁸F‐labelling of amino acids and derivatives for positron emission tomography imaging

From Carbon-11-Labeled Amino Acids to Peptides in Positron Emission Tomography: the Synthesis and Clinical Application

Diastereoselective synthesis of chiral α-aminoorganotributyltins via ring-opening of 2-tributylstannyloxazolidines

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Synthesis of Highly Enantio-Enriched α-Amino Acids by Carboxylation ofN-(α-Lithioalkyl)oxazolidinones

Cited by 31 publications

References 26 publications

Methods for 11C‐ and 18F‐labelling of amino acids and derivatives for positron emission tomography imaging

Methods for 11C‐ and 18F‐labelling of amino acids and derivatives for positron emission tomography imaging

From Carbon-11-Labeled Amino Acids to Peptides in Positron Emission Tomography: the Synthesis and Clinical Application

Diastereoselective synthesis of chiral α-aminoorganotributyltins via ring-opening of 2-tributylstannyloxazolidines

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Product

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Methods for ¹¹C‐ and ¹⁸F‐labelling of amino acids and derivatives for positron emission tomography imaging

Methods for ¹¹C‐ and ¹⁸F‐labelling of amino acids and derivatives for positron emission tomography imaging