Chemoenzymatic synthesis of hygromycin aminocyclitol moiety and its C2 epimer
- Autores
- Carrau, Gonzalo; Bellomo Peraza, Ana Ines; Suescun, Leopoldo; Gonzalez, David
- Año de publicación
- 2018
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- This manuscript describes the enantioselective synthesis of the aminocyclitol moiety of the antibiotic hygromycin A in eight steps and 39 % overall yield from a non-chiral starting material. The sequence made use of an initial enzymatic step to transfer chirality to an aromatic ring and was followed by selective organic chemistry transformations (oxidation, pro-tection, azidation, hydrolysis) of the six-membered ring in order to achieve the target. The approach is also amenable to the synthesis of other related unnatural analogues as exemplified by the synthesis of the C2 epimer of the natural aminocyclitol. All the intermediates were fully characterized, and the absolute stereochemistry assigned by spectrometric methods.
Fil: Carrau, Gonzalo. Universidad de la República; Uruguay
Fil: Bellomo Peraza, Ana Ines. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Parque Centenario. Centro de Investigaciones en Bionanociencias "Elizabeth Jares Erijman"; Argentina
Fil: Suescun, Leopoldo. Universidad de la República; Uruguay
Fil: Gonzalez, David. Universidad de la República; Uruguay - Materia
-
AMINO ALCOHOLS
ASYMMETRIC SYNTHESIS
BIOCATALYSIS
CYCLITOLS
DIHYDROXYLATION - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
- Repositorio
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/123153
Ver los metadatos del registro completo
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Chemoenzymatic synthesis of hygromycin aminocyclitol moiety and its C2 epimerCarrau, GonzaloBellomo Peraza, Ana InesSuescun, LeopoldoGonzalez, DavidAMINO ALCOHOLSASYMMETRIC SYNTHESISBIOCATALYSISCYCLITOLSDIHYDROXYLATIONhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1This manuscript describes the enantioselective synthesis of the aminocyclitol moiety of the antibiotic hygromycin A in eight steps and 39 % overall yield from a non-chiral starting material. The sequence made use of an initial enzymatic step to transfer chirality to an aromatic ring and was followed by selective organic chemistry transformations (oxidation, pro-tection, azidation, hydrolysis) of the six-membered ring in order to achieve the target. The approach is also amenable to the synthesis of other related unnatural analogues as exemplified by the synthesis of the C2 epimer of the natural aminocyclitol. All the intermediates were fully characterized, and the absolute stereochemistry assigned by spectrometric methods.Fil: Carrau, Gonzalo. Universidad de la República; UruguayFil: Bellomo Peraza, Ana Ines. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Parque Centenario. Centro de Investigaciones en Bionanociencias "Elizabeth Jares Erijman"; ArgentinaFil: Suescun, Leopoldo. Universidad de la República; UruguayFil: Gonzalez, David. Universidad de la República; UruguayWiley VCH Verlag2018-11-29info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/123153Carrau, Gonzalo; Bellomo Peraza, Ana Ines; Suescun, Leopoldo; Gonzalez, David; Chemoenzymatic synthesis of hygromycin aminocyclitol moiety and its C2 epimer; Wiley VCH Verlag; European Journal of Organic Chemistry; 2019; 4; 29-11-2018; 788-8021434-193XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.201801424info:eu-repo/semantics/altIdentifier/url/https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/ejoc.201801424info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:40:33Zoai:ri.conicet.gov.ar:11336/123153instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 09:40:33.49CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Chemoenzymatic synthesis of hygromycin aminocyclitol moiety and its C2 epimer |
title |
Chemoenzymatic synthesis of hygromycin aminocyclitol moiety and its C2 epimer |
spellingShingle |
Chemoenzymatic synthesis of hygromycin aminocyclitol moiety and its C2 epimer Carrau, Gonzalo AMINO ALCOHOLS ASYMMETRIC SYNTHESIS BIOCATALYSIS CYCLITOLS DIHYDROXYLATION |
title_short |
Chemoenzymatic synthesis of hygromycin aminocyclitol moiety and its C2 epimer |
title_full |
Chemoenzymatic synthesis of hygromycin aminocyclitol moiety and its C2 epimer |
title_fullStr |
Chemoenzymatic synthesis of hygromycin aminocyclitol moiety and its C2 epimer |
title_full_unstemmed |
Chemoenzymatic synthesis of hygromycin aminocyclitol moiety and its C2 epimer |
title_sort |
Chemoenzymatic synthesis of hygromycin aminocyclitol moiety and its C2 epimer |
dc.creator.none.fl_str_mv |
Carrau, Gonzalo Bellomo Peraza, Ana Ines Suescun, Leopoldo Gonzalez, David |
author |
Carrau, Gonzalo |
author_facet |
Carrau, Gonzalo Bellomo Peraza, Ana Ines Suescun, Leopoldo Gonzalez, David |
author_role |
author |
author2 |
Bellomo Peraza, Ana Ines Suescun, Leopoldo Gonzalez, David |
author2_role |
author author author |
dc.subject.none.fl_str_mv |
AMINO ALCOHOLS ASYMMETRIC SYNTHESIS BIOCATALYSIS CYCLITOLS DIHYDROXYLATION |
topic |
AMINO ALCOHOLS ASYMMETRIC SYNTHESIS BIOCATALYSIS CYCLITOLS DIHYDROXYLATION |
purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
dc.description.none.fl_txt_mv |
This manuscript describes the enantioselective synthesis of the aminocyclitol moiety of the antibiotic hygromycin A in eight steps and 39 % overall yield from a non-chiral starting material. The sequence made use of an initial enzymatic step to transfer chirality to an aromatic ring and was followed by selective organic chemistry transformations (oxidation, pro-tection, azidation, hydrolysis) of the six-membered ring in order to achieve the target. The approach is also amenable to the synthesis of other related unnatural analogues as exemplified by the synthesis of the C2 epimer of the natural aminocyclitol. All the intermediates were fully characterized, and the absolute stereochemistry assigned by spectrometric methods. Fil: Carrau, Gonzalo. Universidad de la República; Uruguay Fil: Bellomo Peraza, Ana Ines. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Parque Centenario. Centro de Investigaciones en Bionanociencias "Elizabeth Jares Erijman"; Argentina Fil: Suescun, Leopoldo. Universidad de la República; Uruguay Fil: Gonzalez, David. Universidad de la República; Uruguay |
description |
This manuscript describes the enantioselective synthesis of the aminocyclitol moiety of the antibiotic hygromycin A in eight steps and 39 % overall yield from a non-chiral starting material. The sequence made use of an initial enzymatic step to transfer chirality to an aromatic ring and was followed by selective organic chemistry transformations (oxidation, pro-tection, azidation, hydrolysis) of the six-membered ring in order to achieve the target. The approach is also amenable to the synthesis of other related unnatural analogues as exemplified by the synthesis of the C2 epimer of the natural aminocyclitol. All the intermediates were fully characterized, and the absolute stereochemistry assigned by spectrometric methods. |
publishDate |
2018 |
dc.date.none.fl_str_mv |
2018-11-29 |
dc.type.none.fl_str_mv |
info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion http://purl.org/coar/resource_type/c_6501 info:ar-repo/semantics/articulo |
format |
article |
status_str |
publishedVersion |
dc.identifier.none.fl_str_mv |
http://hdl.handle.net/11336/123153 Carrau, Gonzalo; Bellomo Peraza, Ana Ines; Suescun, Leopoldo; Gonzalez, David; Chemoenzymatic synthesis of hygromycin aminocyclitol moiety and its C2 epimer; Wiley VCH Verlag; European Journal of Organic Chemistry; 2019; 4; 29-11-2018; 788-802 1434-193X CONICET Digital CONICET |
url |
http://hdl.handle.net/11336/123153 |
identifier_str_mv |
Carrau, Gonzalo; Bellomo Peraza, Ana Ines; Suescun, Leopoldo; Gonzalez, David; Chemoenzymatic synthesis of hygromycin aminocyclitol moiety and its C2 epimer; Wiley VCH Verlag; European Journal of Organic Chemistry; 2019; 4; 29-11-2018; 788-802 1434-193X CONICET Digital CONICET |
dc.language.none.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/doi/10.1002/ejoc.201801424 info:eu-repo/semantics/altIdentifier/url/https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/ejoc.201801424 |
dc.rights.none.fl_str_mv |
info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
eu_rights_str_mv |
openAccess |
rights_invalid_str_mv |
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
dc.format.none.fl_str_mv |
application/pdf application/pdf |
dc.publisher.none.fl_str_mv |
Wiley VCH Verlag |
publisher.none.fl_str_mv |
Wiley VCH Verlag |
dc.source.none.fl_str_mv |
reponame:CONICET Digital (CONICET) instname:Consejo Nacional de Investigaciones Científicas y Técnicas |
reponame_str |
CONICET Digital (CONICET) |
collection |
CONICET Digital (CONICET) |
instname_str |
Consejo Nacional de Investigaciones Científicas y Técnicas |
repository.name.fl_str_mv |
CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas |
repository.mail.fl_str_mv |
dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar |
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13.070432 |