Publication
Multifunctional Imidazole-Derived Polymeric Catalyst for Dephosphorylation Reactions Potentiated by Cationic and Anionic Micelles
| Summary: | Results confirm the catalytic potential of imidazole groups anchored on the polymeric backbone of polyvinylimidazole (PVI) in dephosphorylation reactions with di- and tri-phosphoesters, promoting impressive enhancements up to 107-fold. We propose the imidazole groups on PVI react by nucleophilic catalysis (neutral specie) with a phosphate triester and bifunctionally by general acid-nucleophilic catalysis (bipolar species) with a diester. Additionally, PVI can incorporate the reactants on its domains by hydrophobic and electrostatic attraction, confirming the polymer multifunctionality. Moreover, a pronounced micellar catalysis was observed for the reactions which, surprisingly, occurs with both cationic and anionic micelles, due to favorable approximation effects. The micellar effects observed confirms the reactivity of the bipolar species. Based on the pseudophase model, the reagents can be incorporated in the micellar phase, mainly by hydrophobic forces. Overall, we confirm that PVI has great potential as an artificial enzyme, since it undergoes enzymatic-like mechanisms with an elegant bifunctional catalysis. |
|---|---|
| Main Authors: | Orth,Elisa S. |
| Other Authors: | Campos,Renan B. |
| Subject: | micellar catalysis dephosphorylation imidazole polymeric catalysis |
| Year: | 2016 |
| Country: | Brazil |
| Document type: | article |
| Access type: | open access |
| Associated institution: | IBICT |
| Language: | English |
| Origin: | Oasisbr |
| _version_ | 1871506674060099584 |
|---|---|
| author | Orth,Elisa S. |
| author2 | Campos,Renan B. |
| author2_role | author |
| author_facet | Orth,Elisa S. Campos,Renan B. |
| author_role | author |
| country_str | BR |
| creators_json_txt | [{\"Person.name\":\"Orth,Elisa S.\"},{\"Person.name\":\"Campos,Renan B.\"}] |
| datacite.creators.creator.creatorName.fl_str_mv | Orth,Elisa S. Campos,Renan B. |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| datacite.subjects.subject.fl_str_mv | micellar catalysis dephosphorylation imidazole polymeric catalysis |
| datacite.titles.title.fl_str_mv | Multifunctional Imidazole-Derived Polymeric Catalyst for Dephosphorylation Reactions Potentiated by Cationic and Anionic Micelles |
| dc.creator.none.fl_str_mv | Orth,Elisa S. Campos,Renan B. |
| dc.format.none.fl_str_mv | text/html |
| dc.identifier.none.fl_str_mv | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016000200285 |
| dc.language.none.fl_str_mv | eng |
| dc.publisher.none.fl_str_mv | Sociedade Brasileira de Química |
| dc.rights.none.fl_str_mv | http://purl.org/coar/access_right/c_abf2 |
| dc.source.none.fl_str_mv | Journal of the Brazilian Chemical Society v.27 n.2 2016 reponame:Journal of the Brazilian Chemical Society (Online) instname:Sociedade Brasileira de Química (SBQ) instacron:SBQ |
| dc.subject.none.fl_str_mv | micellar catalysis dephosphorylation imidazole polymeric catalysis |
| dc.title.fl_str_mv | Multifunctional Imidazole-Derived Polymeric Catalyst for Dephosphorylation Reactions Potentiated by Cationic and Anionic Micelles |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_6501 |
| description | Results confirm the catalytic potential of imidazole groups anchored on the polymeric backbone of polyvinylimidazole (PVI) in dephosphorylation reactions with di- and tri-phosphoesters, promoting impressive enhancements up to 107-fold. We propose the imidazole groups on PVI react by nucleophilic catalysis (neutral specie) with a phosphate triester and bifunctionally by general acid-nucleophilic catalysis (bipolar species) with a diester. Additionally, PVI can incorporate the reactants on its domains by hydrophobic and electrostatic attraction, confirming the polymer multifunctionality. Moreover, a pronounced micellar catalysis was observed for the reactions which, surprisingly, occurs with both cationic and anionic micelles, due to favorable approximation effects. The micellar effects observed confirms the reactivity of the bipolar species. Based on the pseudophase model, the reagents can be incorporated in the micellar phase, mainly by hydrophobic forces. Overall, we confirm that PVI has great potential as an artificial enzyme, since it undergoes enzymatic-like mechanisms with an elegant bifunctional catalysis. |
| dirty | 0 |
| eu_rights_str_mv | openAccess |
| format | article |
| id | oasisbr_6052c8a4e550b99e4fa4e87565fe1650 |
| identifier.url.fl_str_mv | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016000200285 |
| inst_facet_str | urn:organizationAcronym:oasisbr{{{_:::_}}}IBICT |
| instacron_str | OASISBR |
| institution | IBICT |
| instname_str | IBICT |
| language | eng |
| network_acronym_str | oasisbr |
| network_name_str | Oasisbr |
| oai_identifier_str | oai:scielo:S0103-50532016000200285 |
| organization_str_mv | urn:organizationAcronym:oasisbr |
| person_str_mv | Orth,Elisa S. Campos,Renan B. |
| publishDate | 2016 |
| publisher.none.fl_str_mv | Sociedade Brasileira de Química |
| repo_facet_str | urn:repositoryAcronym:oasisbr{{{_:::_}}}Oasisbr |
| reponame_str | Oasisbr |
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| service_str_mv | urn:repositoryAcronym:oasisbr |
| spelling | Multifunctional Imidazole-Derived Polymeric Catalyst for Dephosphorylation Reactions Potentiated by Cationic and Anionic MicellesOrth,Elisa S.Campos,Renan B.micellar catalysisdephosphorylationimidazolepolymeric catalysisopen accesshttp://purl.org/coar/access_right/c_abf2http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016000200285URLhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016000200285URLHasVersion2016-02-01Results confirm the catalytic potential of imidazole groups anchored on the polymeric backbone of polyvinylimidazole (PVI) in dephosphorylation reactions with di- and tri-phosphoesters, promoting impressive enhancements up to 107-fold. We propose the imidazole groups on PVI react by nucleophilic catalysis (neutral specie) with a phosphate triester and bifunctionally by general acid-nucleophilic catalysis (bipolar species) with a diester. Additionally, PVI can incorporate the reactants on its domains by hydrophobic and electrostatic attraction, confirming the polymer multifunctionality. Moreover, a pronounced micellar catalysis was observed for the reactions which, surprisingly, occurs with both cationic and anionic micelles, due to favorable approximation effects. The micellar effects observed confirms the reactivity of the bipolar species. Based on the pseudophase model, the reagents can be incorporated in the micellar phase, mainly by hydrophobic forces. Overall, we confirm that PVI has great potential as an artificial enzyme, since it undergoes enzymatic-like mechanisms with an elegant bifunctional catalysis.engtext/htmlSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society v.27 n.2 2016reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQjournal articlehttp://purl.org/coar/resource_type/c_6501literatureVoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85 |
| spellingShingle | Multifunctional Imidazole-Derived Polymeric Catalyst for Dephosphorylation Reactions Potentiated by Cationic and Anionic Micelles Orth,Elisa S. micellar catalysis dephosphorylation imidazole polymeric catalysis |
| status | SINGLETON |
| status_str | VoR |
| subject.fl_str_mv | micellar catalysis dephosphorylation imidazole polymeric catalysis |
| title | Multifunctional Imidazole-Derived Polymeric Catalyst for Dephosphorylation Reactions Potentiated by Cationic and Anionic Micelles |
| title_full | Multifunctional Imidazole-Derived Polymeric Catalyst for Dephosphorylation Reactions Potentiated by Cationic and Anionic Micelles |
| title_fullStr | Multifunctional Imidazole-Derived Polymeric Catalyst for Dephosphorylation Reactions Potentiated by Cationic and Anionic Micelles |
| title_full_unstemmed | Multifunctional Imidazole-Derived Polymeric Catalyst for Dephosphorylation Reactions Potentiated by Cationic and Anionic Micelles |
| title_short | Multifunctional Imidazole-Derived Polymeric Catalyst for Dephosphorylation Reactions Potentiated by Cationic and Anionic Micelles |
| title_sort | Multifunctional Imidazole-Derived Polymeric Catalyst for Dephosphorylation Reactions Potentiated by Cationic and Anionic Micelles |
| topic | micellar catalysis dephosphorylation imidazole polymeric catalysis |
| topic_facet | micellar catalysis dephosphorylation imidazole polymeric catalysis |
| url | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532016000200285 |
| visible | 1 |
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