<div class="csl-bib-body">
<div class="csl-entry">Kratena, N., Demuth, T., Denk, C., Mairinger, S., Langer, O., & Mikula, H. (2024, July 3). <i>Synthesis of a modified ACE2-inhibitor for 18F, 11C and 124I isotopic radiolabelling and PET tracer development</i> [Poster Presentation]. 18th Belgian Organic Synthesis Symposium (BOSS XVIII ), Liege, Belgium. http://hdl.handle.net/20.500.12708/208507</div>
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dc.identifier.uri
http://hdl.handle.net/20.500.12708/208507
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dc.description.abstract
Radiotracers are important molecular tools in the pharmacologists’ toolbox by enabling visualization of adequately radiolabelled compounds through positron-emission-tomography (PET). In this work, a new and a highly convergent synthesis of a very selective ACE2 inhibitor (and of natural occurring L-ergothioenine) is disclosed. Crucially, one of the aromatic chlorides present in the original drug is exchanged by bromine, allowing the introduction of different radioactive isotopes by means of stannylation and subsequent metal-catalyzed modifications. The synthesis commences with the preparation of imidazole hydrochloride 1 (4 steps) which is used to alkylate a t-butyl-protected glycine equivalent 2 in an enantioselective PTC amino acid synthesis. Compound 3, obtained after cleavage of the imine, was reacted in an optimized reductive amination with α-ketoester 4 to obtain the intermediate 5 in good yield. In turn, the subsequent palladium-catalyzed stannylation was performed by transiently protecting the free amine with MSTFA as a strong silylating agent. The key precursor 6 can be isotopically labelled with 18F (copper-mediated radiofluorination), 11C (Stille coupling) or 124I (electrophilic iodination) to give diverse radiotracers for in vivo imaging and investigation of ACE2, the entry port of SARS-CoV2 in human cells.
en
dc.description.sponsorship
FWF - Österr. Wissenschaftsfonds
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dc.language.iso
en
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dc.subject
PET
en
dc.subject
enantioselective synthesis
en
dc.title
Synthesis of a modified ACE2-inhibitor for 18F, 11C and 124I isotopic radiolabelling and PET tracer development
en
dc.type
Presentation
en
dc.type
Vortrag
de
dc.contributor.affiliation
Medical University of Vienna, Austria
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dc.contributor.affiliation
Austrian Institute of Technology, Austria
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dc.relation.grantno
P 33921-B
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dc.type.category
Poster Presentation
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tuw.project.title
Einfluss von Blutdruck Medikamenten auf ACE2 in der Lunge
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tuw.researchinfrastructure
Zentrum für Kernspinresonanzspektroskopie
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tuw.researchTopic.id
M6
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tuw.researchTopic.name
Biological and Bioactive Materials
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tuw.researchTopic.value
100
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tuw.publication.orgunit
E163-03-2 - Forschungsgruppe Molekulare Chemie und Chemische Biologie
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tuw.publication.orgunit
E163-03-3 - Forschungsgruppe Stereoselektive und nachhaltige Chemie
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tuw.author.orcid
0000-0002-3080-7214
-
tuw.author.orcid
0009-0006-4738-6192
-
tuw.author.orcid
0000-0001-5094-9351
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tuw.author.orcid
0000-0002-4048-5781
-
tuw.author.orcid
0000-0002-9218-9722
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tuw.event.name
18th Belgian Organic Synthesis Symposium (BOSS XVIII )
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tuw.event.startdate
30-06-2024
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tuw.event.enddate
05-07-2024
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tuw.event.online
On Site
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tuw.event.type
Event for scientific audience
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tuw.event.place
Liege
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tuw.event.country
BE
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tuw.event.presenter
Kratena, Nicolas
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tuw.event.track
Single Track
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wb.sciencebranch
Chemie
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wb.sciencebranch
Chemische Verfahrenstechnik
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wb.sciencebranch
Pharmazie, Pharmakologie, Toxikologie
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wb.sciencebranch.oefos
1040
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wb.sciencebranch.oefos
2040
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wb.sciencebranch.oefos
3012
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wb.sciencebranch.value
60
-
wb.sciencebranch.value
20
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wb.sciencebranch.value
20
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item.cerifentitytype
Publications
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item.languageiso639-1
en
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item.fulltext
no Fulltext
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item.openairetype
conference poster not in proceedings
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item.openairecristype
http://purl.org/coar/resource_type/c_18co
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item.grantfulltext
none
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crisitem.project.funder
FWF - Österr. Wissenschaftsfonds
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crisitem.project.grantno
P 33921-B
-
crisitem.author.dept
E163-03-3 - Forschungsgruppe Stereoselektive und nachhaltige Chemie
-
crisitem.author.dept
E163-03-2 - Forschungsgruppe Molekulare Chemie und Chemische Biologie
-
crisitem.author.dept
E163-03-2 - Forschungsgruppe Molekulare Chemie und Chemische Biologie
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crisitem.author.dept
Medical University of Vienna
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crisitem.author.dept
Austrian Institute of Technology
-
crisitem.author.dept
E163-03-2 - Forschungsgruppe Molekulare Chemie und Chemische Biologie
-
crisitem.author.orcid
0000-0002-3080-7214
-
crisitem.author.orcid
0009-0006-4738-6192
-
crisitem.author.orcid
0000-0002-4048-5781
-
crisitem.author.orcid
0000-0002-9218-9722
-
crisitem.author.parentorg
E163-03 - Forschungsbereich Organische und Biologische Chemie
-
crisitem.author.parentorg
E163-03 - Forschungsbereich Organische und Biologische Chemie
-
crisitem.author.parentorg
E163-03 - Forschungsbereich Organische und Biologische Chemie
-
crisitem.author.parentorg
E163-03 - Forschungsbereich Organische und Biologische Chemie
