<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>
</div>
-
dc.identifier.uri
http://hdl.handle.net/20.500.12708/208507
-
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
-
dc.language.iso
en
-
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
-
dc.contributor.affiliation
Austrian Institute of Technology, Austria
-
dc.relation.grantno
P 33921-B
-
dc.type.category
Poster Presentation
-
tuw.project.title
Einfluss von Blutdruck Medikamenten auf ACE2 in der Lunge
-
tuw.researchinfrastructure
Zentrum für Kernspinresonanzspektroskopie
-
tuw.researchTopic.id
M6
-
tuw.researchTopic.name
Biological and Bioactive Materials
-
tuw.researchTopic.value
100
-
tuw.publication.orgunit
E163-03-2 - Forschungsgruppe Molekulare Chemie und Chemische Biologie
-
tuw.publication.orgunit
E163-03-3 - Forschungsgruppe Stereoselektive und nachhaltige Chemie
-
tuw.author.orcid
0000-0002-3080-7214
-
tuw.author.orcid
0009-0006-4738-6192
-
tuw.author.orcid
0000-0001-5094-9351
-
tuw.author.orcid
0000-0002-4048-5781
-
tuw.author.orcid
0000-0002-9218-9722
-
tuw.event.name
18th Belgian Organic Synthesis Symposium (BOSS XVIII )
-
tuw.event.startdate
30-06-2024
-
tuw.event.enddate
05-07-2024
-
tuw.event.online
On Site
-
tuw.event.type
Event for scientific audience
-
tuw.event.place
Liege
-
tuw.event.country
BE
-
tuw.event.presenter
Kratena, Nicolas
-
tuw.event.track
Single Track
-
wb.sciencebranch
Chemie
-
wb.sciencebranch
Chemische Verfahrenstechnik
-
wb.sciencebranch
Pharmazie, Pharmakologie, Toxikologie
-
wb.sciencebranch.oefos
1040
-
wb.sciencebranch.oefos
2040
-
wb.sciencebranch.oefos
3012
-
wb.sciencebranch.value
60
-
wb.sciencebranch.value
20
-
wb.sciencebranch.value
20
-
item.languageiso639-1
en
-
item.openairetype
conference poster not in proceedings
-
item.openairecristype
http://purl.org/coar/resource_type/c_18co
-
item.grantfulltext
none
-
item.cerifentitytype
Publications
-
item.fulltext
no Fulltext
-
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
-
crisitem.author.dept
Medical University of Vienna
-
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
