Sugar bislactones by one-step oxidative dimerisation with pyridinium chlorochromate versus regioselective oxidation of vicinal diols
Autor(a) principal: | |
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Data de Publicação: | 2004 |
Outros Autores: | , , , , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10400.15/4548 |
Resumo: | Synthesis of 10-membered bislactones by PCC oxidation of methyl 2,6-di-O-pivaloyl-α-D-glucopyranoside and methyl 4,6-O-benzylidene-α-D-glucopyranoside is described, with emphasis on their structure elucidation using the information gained by combination of NMR spectroscopic techniques with X-ray diffraction data. In alternative, the use of PCC and PCC adsorbed on silica gel or alumina for the regioselective oxidation of vicinal diols in sugars is also reported. Both bislactones showed antifungal activity against Candida albicans, and were slightly active against the bacteria Bacillus subtilis. The bislactone presenting pivaloyl protecting groups also promoted some growth inhibition of Staphylococcus aureus. |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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7160 |
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Sugar bislactones by one-step oxidative dimerisation with pyridinium chlorochromate versus regioselective oxidation of vicinal diolssugar bislactonesketo sugarspyridinium chlorochromateregioselective oxidationbioactivity studiesSynthesis of 10-membered bislactones by PCC oxidation of methyl 2,6-di-O-pivaloyl-α-D-glucopyranoside and methyl 4,6-O-benzylidene-α-D-glucopyranoside is described, with emphasis on their structure elucidation using the information gained by combination of NMR spectroscopic techniques with X-ray diffraction data. In alternative, the use of PCC and PCC adsorbed on silica gel or alumina for the regioselective oxidation of vicinal diols in sugars is also reported. Both bislactones showed antifungal activity against Candida albicans, and were slightly active against the bacteria Bacillus subtilis. The bislactone presenting pivaloyl protecting groups also promoted some growth inhibition of Staphylococcus aureus.ElsevierRepositório Científico do Instituto Politécnico de SantarémRauter, A. P.Piedade, F.Almeida, T.Ramalho, R.Ferreira, M.J.Resende, R.Amado, J.Pereira, H.Justino, JorgeNeves, AnaSilva, Filipa V.M.Canda, T.2023-09-18T13:50:54Z2004-082004-08-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10400.15/4548engRauter, A.P.; Piedade, F.; Almeida, T.; Ramalho, R.; Ferreira, M.J.; Resende, R.; Amado, J.; Pereira, H.; Justino, J.; Neves, A.; Silva, F.V.M. & Canda, T. (2004). Sugar bislactones by one-step oxidative dimerisation with pyridinium chlorochromate versus regioselective oxidation of vicinal diols. Carbohydrate Research, 339(11), 1889-1897. DOI:10.1016/j.carres.2004.06.0020008-621510.1016/j.carres.2004.06.002info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2024-01-21T07:38:10Zoai:repositorio.ipsantarem.pt:10400.15/4548Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T01:56:08.162837Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
dc.title.none.fl_str_mv |
Sugar bislactones by one-step oxidative dimerisation with pyridinium chlorochromate versus regioselective oxidation of vicinal diols |
title |
Sugar bislactones by one-step oxidative dimerisation with pyridinium chlorochromate versus regioselective oxidation of vicinal diols |
spellingShingle |
Sugar bislactones by one-step oxidative dimerisation with pyridinium chlorochromate versus regioselective oxidation of vicinal diols Rauter, A. P. sugar bislactones keto sugars pyridinium chlorochromate regioselective oxidation bioactivity studies |
title_short |
Sugar bislactones by one-step oxidative dimerisation with pyridinium chlorochromate versus regioselective oxidation of vicinal diols |
title_full |
Sugar bislactones by one-step oxidative dimerisation with pyridinium chlorochromate versus regioselective oxidation of vicinal diols |
title_fullStr |
Sugar bislactones by one-step oxidative dimerisation with pyridinium chlorochromate versus regioselective oxidation of vicinal diols |
title_full_unstemmed |
Sugar bislactones by one-step oxidative dimerisation with pyridinium chlorochromate versus regioselective oxidation of vicinal diols |
title_sort |
Sugar bislactones by one-step oxidative dimerisation with pyridinium chlorochromate versus regioselective oxidation of vicinal diols |
author |
Rauter, A. P. |
author_facet |
Rauter, A. P. Piedade, F. Almeida, T. Ramalho, R. Ferreira, M.J. Resende, R. Amado, J. Pereira, H. Justino, Jorge Neves, Ana Silva, Filipa V.M. Canda, T. |
author_role |
author |
author2 |
Piedade, F. Almeida, T. Ramalho, R. Ferreira, M.J. Resende, R. Amado, J. Pereira, H. Justino, Jorge Neves, Ana Silva, Filipa V.M. Canda, T. |
author2_role |
author author author author author author author author author author author |
dc.contributor.none.fl_str_mv |
Repositório Científico do Instituto Politécnico de Santarém |
dc.contributor.author.fl_str_mv |
Rauter, A. P. Piedade, F. Almeida, T. Ramalho, R. Ferreira, M.J. Resende, R. Amado, J. Pereira, H. Justino, Jorge Neves, Ana Silva, Filipa V.M. Canda, T. |
dc.subject.por.fl_str_mv |
sugar bislactones keto sugars pyridinium chlorochromate regioselective oxidation bioactivity studies |
topic |
sugar bislactones keto sugars pyridinium chlorochromate regioselective oxidation bioactivity studies |
description |
Synthesis of 10-membered bislactones by PCC oxidation of methyl 2,6-di-O-pivaloyl-α-D-glucopyranoside and methyl 4,6-O-benzylidene-α-D-glucopyranoside is described, with emphasis on their structure elucidation using the information gained by combination of NMR spectroscopic techniques with X-ray diffraction data. In alternative, the use of PCC and PCC adsorbed on silica gel or alumina for the regioselective oxidation of vicinal diols in sugars is also reported. Both bislactones showed antifungal activity against Candida albicans, and were slightly active against the bacteria Bacillus subtilis. The bislactone presenting pivaloyl protecting groups also promoted some growth inhibition of Staphylococcus aureus. |
publishDate |
2004 |
dc.date.none.fl_str_mv |
2004-08 2004-08-01T00:00:00Z 2023-09-18T13:50:54Z |
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/10400.15/4548 |
url |
http://hdl.handle.net/10400.15/4548 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Rauter, A.P.; Piedade, F.; Almeida, T.; Ramalho, R.; Ferreira, M.J.; Resende, R.; Amado, J.; Pereira, H.; Justino, J.; Neves, A.; Silva, F.V.M. & Canda, T. (2004). Sugar bislactones by one-step oxidative dimerisation with pyridinium chlorochromate versus regioselective oxidation of vicinal diols. Carbohydrate Research, 339(11), 1889-1897. DOI:10.1016/j.carres.2004.06.002 0008-6215 10.1016/j.carres.2004.06.002 |
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.publisher.none.fl_str_mv |
Elsevier |
publisher.none.fl_str_mv |
Elsevier |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
instname_str |
Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
instacron_str |
RCAAP |
institution |
RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
collection |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
repository.name.fl_str_mv |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
repository.mail.fl_str_mv |
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1799137050368147456 |