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Synthesis, Conformational Analysis, and Complexation Study of an Iminosugar-Aza-Crown, a Sweet Chiral Cyclam Analog
[Image: see text] A new family of chiral C(2) symmetric tetraazamacrocycles, coined ISAC for IminoSugar Aza-Crown, incorporating two iminosugars adopting a (4)C(1) conformation is disclosed. Multinuclear NMR experiments on the corresponding Cd(2+) complex show that the ISAC is a strong chelator in w...
| Autores principales: | , , , , , , , , , , , , |
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| Formato: | Online Artículo Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical Society
2020
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7114874/ https://www.ncbi.nlm.nih.gov/pubmed/32153195 http://dx.doi.org/10.1021/acs.orglett.0c00503 |
| _version_ | 1783513980837298176 |
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| author | Bordes, Alexandra Poveda, Ana Troadec, Thibault Franconetti, Antonio Ardá, Ana Perrin, Flavie Ménand, Mickaël Sollogoub, Matthieu Guillard, Jerôme Désiré, Jérôme Tripier, Raphaël Jiménez-Barbero, Jesús Blériot, Yves |
| author_facet | Bordes, Alexandra Poveda, Ana Troadec, Thibault Franconetti, Antonio Ardá, Ana Perrin, Flavie Ménand, Mickaël Sollogoub, Matthieu Guillard, Jerôme Désiré, Jérôme Tripier, Raphaël Jiménez-Barbero, Jesús Blériot, Yves |
| author_sort | Bordes, Alexandra |
| collection | PubMed |
| description | [Image: see text] A new family of chiral C(2) symmetric tetraazamacrocycles, coined ISAC for IminoSugar Aza-Crown, incorporating two iminosugars adopting a (4)C(1) conformation is disclosed. Multinuclear NMR experiments on the corresponding Cd(2+) complex show that the ISAC is a strong chelator in water and its tetramine cavity adopts a conformation similar to that of the parent Cd–cyclam complex. Similar behavior is observed with Cu(2+) in solution, with enhanced stability compared to the Cu–cyclam complex. |
| format | Online Article Text |
| id | pubmed-7114874 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2020 |
| publisher | American Chemical Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-71148742020-04-03 Synthesis, Conformational Analysis, and Complexation Study of an Iminosugar-Aza-Crown, a Sweet Chiral Cyclam Analog Bordes, Alexandra Poveda, Ana Troadec, Thibault Franconetti, Antonio Ardá, Ana Perrin, Flavie Ménand, Mickaël Sollogoub, Matthieu Guillard, Jerôme Désiré, Jérôme Tripier, Raphaël Jiménez-Barbero, Jesús Blériot, Yves Org Lett [Image: see text] A new family of chiral C(2) symmetric tetraazamacrocycles, coined ISAC for IminoSugar Aza-Crown, incorporating two iminosugars adopting a (4)C(1) conformation is disclosed. Multinuclear NMR experiments on the corresponding Cd(2+) complex show that the ISAC is a strong chelator in water and its tetramine cavity adopts a conformation similar to that of the parent Cd–cyclam complex. Similar behavior is observed with Cu(2+) in solution, with enhanced stability compared to the Cu–cyclam complex. American Chemical Society 2020-03-10 2020-03-20 /pmc/articles/PMC7114874/ /pubmed/32153195 http://dx.doi.org/10.1021/acs.orglett.0c00503 Text en Copyright © 2020 American Chemical Society This is an open access article published under a Creative Commons Non-Commercial No Derivative Works (CC-BY-NC-ND) Attribution License (http://pubs.acs.org/page/policy/authorchoice_ccbyncnd_termsofuse.html) , which permits copying and redistribution of the article, and creation of adaptations, all for non-commercial purposes. |
| spellingShingle | Bordes, Alexandra Poveda, Ana Troadec, Thibault Franconetti, Antonio Ardá, Ana Perrin, Flavie Ménand, Mickaël Sollogoub, Matthieu Guillard, Jerôme Désiré, Jérôme Tripier, Raphaël Jiménez-Barbero, Jesús Blériot, Yves Synthesis, Conformational Analysis, and Complexation Study of an Iminosugar-Aza-Crown, a Sweet Chiral Cyclam Analog |
| title | Synthesis, Conformational Analysis, and Complexation
Study of an Iminosugar-Aza-Crown, a Sweet Chiral Cyclam Analog |
| title_full | Synthesis, Conformational Analysis, and Complexation
Study of an Iminosugar-Aza-Crown, a Sweet Chiral Cyclam Analog |
| title_fullStr | Synthesis, Conformational Analysis, and Complexation
Study of an Iminosugar-Aza-Crown, a Sweet Chiral Cyclam Analog |
| title_full_unstemmed | Synthesis, Conformational Analysis, and Complexation
Study of an Iminosugar-Aza-Crown, a Sweet Chiral Cyclam Analog |
| title_short | Synthesis, Conformational Analysis, and Complexation
Study of an Iminosugar-Aza-Crown, a Sweet Chiral Cyclam Analog |
| title_sort | synthesis, conformational analysis, and complexation
study of an iminosugar-aza-crown, a sweet chiral cyclam analog |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7114874/ https://www.ncbi.nlm.nih.gov/pubmed/32153195 http://dx.doi.org/10.1021/acs.orglett.0c00503 |
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