Synthetic approaches to a challenging and unusual structure—an amino-pyrrolidine guanine core

Bibliographic Details
Main Author: Rippel, Rafael
Publication Date: 2020
Other Authors: Pinheiro, Luís, Lopes, Mónica, Lourenço, Ana, Ferreira, Luísa M., Branco, Paula S.
Format: Article
Language: eng
Source: Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
Download full: http://hdl.handle.net/10362/105370
Summary: Associate Laboratory for Green Chemistry-LAQV, which is financed by national funds from FCT/MCTES (UIDB/50006/2020). Grant number SFRH/BD/136692/2018 from FCT/MCTES.
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oai_identifier_str oai:run.unl.pt:10362/105370
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network_name_str Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
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spelling Synthetic approaches to a challenging and unusual structure—an amino-pyrrolidine guanine coreAmino acid decarboxylationCernumidineCyclic-guanidineRadical decarboxylationAnalytical ChemistryChemistry (miscellaneous)Molecular MedicinePharmaceutical ScienceDrug DiscoveryPhysical and Theoretical ChemistryOrganic ChemistryAssociate Laboratory for Green Chemistry-LAQV, which is financed by national funds from FCT/MCTES (UIDB/50006/2020). Grant number SFRH/BD/136692/2018 from FCT/MCTES.The synthesis of an unreported 2-aminopyrrolidine-1-carboxamidine unit is here described for the first time. This unusual and promising structure was attained through the oxidative decarboxylation of amino acids using the pair of reagents, silver(I)/peroxydisulfate (Ag(I)/S2O82−) followed by intermolecular (in the case of L-proline derivative) and intramolecular trapping (in the case of acyl L-arginine) by N-nucleophiles. The L-proline approach has a broader scope for the synthesis of 2-aminopyrrolidine-1-carboxamidine derivatives, whereas the intramolecular cyclization afforded by the L-acylarginines, when applied, results in higher yields. The former allowed the first synthesis of cernumidine, a natural alkaloid isolated in 2011 from Solanum cernuum Vell, as its racemic form.LAQV@REQUIMTERUNRippel, RafaelPinheiro, LuísLopes, MónicaLourenço, AnaFerreira, Luísa M.Branco, Paula S.2020-10-09T22:50:02Z2020-02-122020-02-12T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10362/105370engPURE: 20261279https://doi.org/10.3390/molecules25040797info:eu-repo/semantics/openAccessreponame:Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)instname:FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologiainstacron:RCAAP2024-05-22T17:48:00Zoai:run.unl.pt:10362/105370Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireinfo@rcaap.ptopendoar:https://opendoar.ac.uk/repository/71602025-05-28T17:19:03.239475Repositórios Científicos de Acesso Aberto de Portugal (RCAAP) - FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologiafalse
dc.title.none.fl_str_mv Synthetic approaches to a challenging and unusual structure—an amino-pyrrolidine guanine core
title Synthetic approaches to a challenging and unusual structure—an amino-pyrrolidine guanine core
spellingShingle Synthetic approaches to a challenging and unusual structure—an amino-pyrrolidine guanine core
Rippel, Rafael
Amino acid decarboxylation
Cernumidine
Cyclic-guanidine
Radical decarboxylation
Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry
title_short Synthetic approaches to a challenging and unusual structure—an amino-pyrrolidine guanine core
title_full Synthetic approaches to a challenging and unusual structure—an amino-pyrrolidine guanine core
title_fullStr Synthetic approaches to a challenging and unusual structure—an amino-pyrrolidine guanine core
title_full_unstemmed Synthetic approaches to a challenging and unusual structure—an amino-pyrrolidine guanine core
title_sort Synthetic approaches to a challenging and unusual structure—an amino-pyrrolidine guanine core
author Rippel, Rafael
author_facet Rippel, Rafael
Pinheiro, Luís
Lopes, Mónica
Lourenço, Ana
Ferreira, Luísa M.
Branco, Paula S.
author_role author
author2 Pinheiro, Luís
Lopes, Mónica
Lourenço, Ana
Ferreira, Luísa M.
Branco, Paula S.
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv LAQV@REQUIMTE
RUN
dc.contributor.author.fl_str_mv Rippel, Rafael
Pinheiro, Luís
Lopes, Mónica
Lourenço, Ana
Ferreira, Luísa M.
Branco, Paula S.
dc.subject.por.fl_str_mv Amino acid decarboxylation
Cernumidine
Cyclic-guanidine
Radical decarboxylation
Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry
topic Amino acid decarboxylation
Cernumidine
Cyclic-guanidine
Radical decarboxylation
Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry
description Associate Laboratory for Green Chemistry-LAQV, which is financed by national funds from FCT/MCTES (UIDB/50006/2020). Grant number SFRH/BD/136692/2018 from FCT/MCTES.
publishDate 2020
dc.date.none.fl_str_mv 2020-10-09T22:50:02Z
2020-02-12
2020-02-12T00:00:00Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/10362/105370
url http://hdl.handle.net/10362/105370
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv PURE: 20261279
https://doi.org/10.3390/molecules25040797
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
instname:FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologia
instacron:RCAAP
instname_str FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologia
instacron_str RCAAP
institution RCAAP
reponame_str Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
collection Repositórios Científicos de Acesso Aberto de Portugal (RCAAP)
repository.name.fl_str_mv Repositórios Científicos de Acesso Aberto de Portugal (RCAAP) - FCCN, serviços digitais da FCT – Fundação para a Ciência e a Tecnologia
repository.mail.fl_str_mv info@rcaap.pt
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