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
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/123153
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/123153
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling 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 Técnicas2025-10-22T11:09:12Zoai: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:34982025-10-22 11:09:12.413CONICET 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
_version_ 1846781432864702464
score 12.982451

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