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: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

^*Corresponding author for this work

Imaging Chemistry & Biology

VU Amsterdam

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

9 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
Early online date	14 Sept 2017
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

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10.1002/ejoc.201700932

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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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doi = "10.1002/ejoc.201700932",

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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

UR - http://www.scopus.com/inward/record.url?scp=85029445425&partnerID=8YFLogxK

U2 - 10.1002/ejoc.201700932

DO - 10.1002/ejoc.201700932

M3 - Article

AN - SCOPUS:85029445425

SN - 1434-193X

VL - 2017

SP - 5154

EP - 5162

JO - EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

JF - EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

IS - 34

ER -

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

Abstract

Keywords

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