Efficient Synthesis of 11C-Acrylesters, 11C-Acrylamides and Their Application in Michael Addition Reactions for PET Tracer Development

Ulrike Filp; Anna L. Pees; Carlotta Taddei; Aleksandra Pekošak; Antony D. Gee; Albert D. Windhorst; Alex J. Poot

doi:https://doi.org/10.1002/ejoc.201700932

Efficient Synthesis of ¹¹C-Acrylesters, ¹¹C-Acrylamides and Their Application in Michael Addition Reactions for PET Tracer Development

Ulrike Filp, Anna L. Pees, Carlotta Taddei, Aleksandra Pekošak, Antony D. Gee, Albert D. Windhorst, Alex J. Poot

Research output: Contribution to journal › Article › Academic › peer-review

8 Citations (Scopus)

Abstract

Here we present a new Michael addition reaction utilizing carbon-11 labeled acrylic esters and amides. Subsequently, reactions of these synthons with commercially available Schiff base precursors are performed to produce [¹¹C]glutamate and [¹¹C]glutamine. This methodology is especially useful for the development of positron emission tomography (PET) imaging agents as it offers a new array of potential carbon-11 labeled compounds with this original ¹¹C–C bond forming strategy.

Original language	English
Pages (from-to)	5154-5162
Number of pages	9
Journal	European Journal of Organic Chemistry
Volume	2017
Issue number	34
DOIs	https://doi.org/10.1002/ejoc.201700932
Publication status	Published - 15 Sept 2017

Keywords

Amino acids
Carbonylation
Michael addition
Positron emission tomography
Radiochemistry
Schiff bases

Access to Document

https://doi.org/10.1002/ejoc.201700932

Cite this

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title = "Efficient Synthesis of 11C-Acrylesters, 11C-Acrylamides and Their Application in Michael Addition Reactions for PET Tracer Development",

abstract = "Here we present a new Michael addition reaction utilizing carbon-11 labeled acrylic esters and amides. Subsequently, reactions of these synthons with commercially available Schiff base precursors are performed to produce [11C]glutamate and [11C]glutamine. This methodology is especially useful for the development of positron emission tomography (PET) imaging agents as it offers a new array of potential carbon-11 labeled compounds with this original 11C–C bond forming strategy.",

keywords = "Amino acids, Carbonylation, Michael addition, Positron emission tomography, Radiochemistry, Schiff bases",

author = "Ulrike Filp and Pees, {Anna L.} and Carlotta Taddei and Aleksandra Peko{\v s}ak and Gee, {Antony D.} and Windhorst, {Albert D.} and Poot, {Alex J.}",

year = "2017",

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language = "English",

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TY - JOUR

T1 - Efficient Synthesis of 11C-Acrylesters, 11C-Acrylamides and Their Application in Michael Addition Reactions for PET Tracer Development

AU - Filp, Ulrike

AU - Pees, Anna L.

AU - Taddei, Carlotta

AU - Pekošak, Aleksandra

AU - Gee, Antony D.

AU - Windhorst, Albert D.

AU - Poot, Alex J.

PY - 2017/9/15

Y1 - 2017/9/15

N2 - Here we present a new Michael addition reaction utilizing carbon-11 labeled acrylic esters and amides. Subsequently, reactions of these synthons with commercially available Schiff base precursors are performed to produce [11C]glutamate and [11C]glutamine. This methodology is especially useful for the development of positron emission tomography (PET) imaging agents as it offers a new array of potential carbon-11 labeled compounds with this original 11C–C bond forming strategy.

AB - Here we present a new Michael addition reaction utilizing carbon-11 labeled acrylic esters and amides. Subsequently, reactions of these synthons with commercially available Schiff base precursors are performed to produce [11C]glutamate and [11C]glutamine. This methodology is especially useful for the development of positron emission tomography (PET) imaging agents as it offers a new array of potential carbon-11 labeled compounds with this original 11C–C bond forming strategy.

KW - Amino acids

KW - Carbonylation

KW - Michael addition

KW - Positron emission tomography

KW - Radiochemistry

KW - Schiff bases

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U2 - https://doi.org/10.1002/ejoc.201700932

DO - https://doi.org/10.1002/ejoc.201700932

M3 - Article

SN - 1434-193X

VL - 2017

SP - 5154

EP - 5162

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 34

ER -