Synthesis of alpha-D-Glcp-(1-3)-alpha-D-Galf-(1-2)-alpha-L-Rhap constituent of the CPS of Streptococcus pneumoniae 22F. Effect of 3-O-substitution in 1,2-cis alpha-D-galactofuranos...

Autores
Gola, Gabriel; Gallo, Carola
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The synthesis of the trisaccharide a-D-Glcp-(1-3)-a-D-Galf-(1-2)-L-Rhap (3) constituent of Streptococcus pneumonia 22F was achieved with complete diastereoselectively. This is the first example of a synthesis of an internal a-D-Galf containing oligosaccharide of a pathogen microorganism. Allyl α-D-galactofuranoside, used as novel precursor of the internal Galf, allowed the introduction of an orthogonal group at O-3. The trichloroacetimidate method was used for the construction of 1,2-cis a-D-galactofuranosyl linkage. The influence of the 3-O-substituent (PMB, Bz, PFBz, PMBz, TIPS) was evaluated in benzylated galactofuranosyl trichloroacetimidate donors in terms of yield and selectivity of a-D-Galf-(1-2)-a-L-Rhap product as well as donor rearrangement by-product. Complete stereoselectivity was observed with all protecting groups used in Galf donor, but the 3-O-benzoyl substitution gave the best yield. Protective groups were also evaluated in rhamnoside acceptor, benzyl substitution was a requirement for complete stereoselectivity.
Fil: Gola, Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Gallo, Carola. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina
Materia
Glycosylation 1,2-Cis
Substitution Effect
Galactofuranose
Oligosaccharide
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:11336/8157
Acceder
id CONICETDig_ef4e2eca070492f3406c339820177325
oai_identifier_str oai:ri.conicet.gov.ar:11336/8157
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis of alpha-D-Glcp-(1-3)-alpha-D-Galf-(1-2)-alpha-L-Rhap constituent of the CPS of Streptococcus pneumoniae 22F. Effect of 3-O-substitution in 1,2-cis alpha-D-galactofuranosylationGola, GabrielGallo, CarolaGlycosylation 1,2-CisSubstitution EffectGalactofuranoseOligosaccharidehttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The synthesis of the trisaccharide a-D-Glcp-(1-3)-a-D-Galf-(1-2)-L-Rhap (3) constituent of Streptococcus pneumonia 22F was achieved with complete diastereoselectively. This is the first example of a synthesis of an internal a-D-Galf containing oligosaccharide of a pathogen microorganism. Allyl α-D-galactofuranoside, used as novel precursor of the internal Galf, allowed the introduction of an orthogonal group at O-3. The trichloroacetimidate method was used for the construction of 1,2-cis a-D-galactofuranosyl linkage. The influence of the 3-O-substituent (PMB, Bz, PFBz, PMBz, TIPS) was evaluated in benzylated galactofuranosyl trichloroacetimidate donors in terms of yield and selectivity of a-D-Galf-(1-2)-a-L-Rhap product as well as donor rearrangement by-product. Complete stereoselectivity was observed with all protecting groups used in Galf donor, but the 3-O-benzoyl substitution gave the best yield. Protective groups were also evaluated in rhamnoside acceptor, benzyl substitution was a requirement for complete stereoselectivity.Fil: Gola, Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; ArgentinaFil: Gallo, Carola. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; ArgentinaRoyal Society of Chemistry2014-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/8157Gola, Gabriel; Gallo, Carola; Synthesis of alpha-D-Glcp-(1-3)-alpha-D-Galf-(1-2)-alpha-L-Rhap constituent of the CPS of Streptococcus pneumoniae 22F. Effect of 3-O-substitution in 1,2-cis alpha-D-galactofuranosylation; Royal Society of Chemistry; RSC Advances; 4; 7; 1-2014; 3368-33822046-2069enginfo:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2014/RA/C3RA45658G#!divAbstractinfo:eu-repo/semantics/altIdentifier/doi/10.1039/C3RA45658Ginfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:46:53Zoai:ri.conicet.gov.ar:11336/8157instacron: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:34982025-10-15 14:46:54.182CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of alpha-D-Glcp-(1-3)-alpha-D-Galf-(1-2)-alpha-L-Rhap constituent of the CPS of Streptococcus pneumoniae 22F. Effect of 3-O-substitution in 1,2-cis alpha-D-galactofuranosylation
title Synthesis of alpha-D-Glcp-(1-3)-alpha-D-Galf-(1-2)-alpha-L-Rhap constituent of the CPS of Streptococcus pneumoniae 22F. Effect of 3-O-substitution in 1,2-cis alpha-D-galactofuranosylation
spellingShingle Synthesis of alpha-D-Glcp-(1-3)-alpha-D-Galf-(1-2)-alpha-L-Rhap constituent of the CPS of Streptococcus pneumoniae 22F. Effect of 3-O-substitution in 1,2-cis alpha-D-galactofuranosylation
Gola, Gabriel
Glycosylation 1,2-Cis
Substitution Effect
Galactofuranose
Oligosaccharide
title_short Synthesis of alpha-D-Glcp-(1-3)-alpha-D-Galf-(1-2)-alpha-L-Rhap constituent of the CPS of Streptococcus pneumoniae 22F. Effect of 3-O-substitution in 1,2-cis alpha-D-galactofuranosylation
title_full Synthesis of alpha-D-Glcp-(1-3)-alpha-D-Galf-(1-2)-alpha-L-Rhap constituent of the CPS of Streptococcus pneumoniae 22F. Effect of 3-O-substitution in 1,2-cis alpha-D-galactofuranosylation
title_fullStr Synthesis of alpha-D-Glcp-(1-3)-alpha-D-Galf-(1-2)-alpha-L-Rhap constituent of the CPS of Streptococcus pneumoniae 22F. Effect of 3-O-substitution in 1,2-cis alpha-D-galactofuranosylation
title_full_unstemmed Synthesis of alpha-D-Glcp-(1-3)-alpha-D-Galf-(1-2)-alpha-L-Rhap constituent of the CPS of Streptococcus pneumoniae 22F. Effect of 3-O-substitution in 1,2-cis alpha-D-galactofuranosylation
title_sort Synthesis of alpha-D-Glcp-(1-3)-alpha-D-Galf-(1-2)-alpha-L-Rhap constituent of the CPS of Streptococcus pneumoniae 22F. Effect of 3-O-substitution in 1,2-cis alpha-D-galactofuranosylation
dc.creator.none.fl_str_mv Gola, Gabriel
Gallo, Carola
author Gola, Gabriel
author_facet Gola, Gabriel
Gallo, Carola
author_role author
author2 Gallo, Carola
author2_role author
dc.subject.none.fl_str_mv Glycosylation 1,2-Cis
Substitution Effect
Galactofuranose
Oligosaccharide
topic Glycosylation 1,2-Cis
Substitution Effect
Galactofuranose
Oligosaccharide
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The synthesis of the trisaccharide a-D-Glcp-(1-3)-a-D-Galf-(1-2)-L-Rhap (3) constituent of Streptococcus pneumonia 22F was achieved with complete diastereoselectively. This is the first example of a synthesis of an internal a-D-Galf containing oligosaccharide of a pathogen microorganism. Allyl α-D-galactofuranoside, used as novel precursor of the internal Galf, allowed the introduction of an orthogonal group at O-3. The trichloroacetimidate method was used for the construction of 1,2-cis a-D-galactofuranosyl linkage. The influence of the 3-O-substituent (PMB, Bz, PFBz, PMBz, TIPS) was evaluated in benzylated galactofuranosyl trichloroacetimidate donors in terms of yield and selectivity of a-D-Galf-(1-2)-a-L-Rhap product as well as donor rearrangement by-product. Complete stereoselectivity was observed with all protecting groups used in Galf donor, but the 3-O-benzoyl substitution gave the best yield. Protective groups were also evaluated in rhamnoside acceptor, benzyl substitution was a requirement for complete stereoselectivity.
Fil: Gola, Gabriel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina
Fil: Gallo, Carola. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina
description The synthesis of the trisaccharide a-D-Glcp-(1-3)-a-D-Galf-(1-2)-L-Rhap (3) constituent of Streptococcus pneumonia 22F was achieved with complete diastereoselectively. This is the first example of a synthesis of an internal a-D-Galf containing oligosaccharide of a pathogen microorganism. Allyl α-D-galactofuranoside, used as novel precursor of the internal Galf, allowed the introduction of an orthogonal group at O-3. The trichloroacetimidate method was used for the construction of 1,2-cis a-D-galactofuranosyl linkage. The influence of the 3-O-substituent (PMB, Bz, PFBz, PMBz, TIPS) was evaluated in benzylated galactofuranosyl trichloroacetimidate donors in terms of yield and selectivity of a-D-Galf-(1-2)-a-L-Rhap product as well as donor rearrangement by-product. Complete stereoselectivity was observed with all protecting groups used in Galf donor, but the 3-O-benzoyl substitution gave the best yield. Protective groups were also evaluated in rhamnoside acceptor, benzyl substitution was a requirement for complete stereoselectivity.
publishDate 2014
dc.date.none.fl_str_mv 2014-01
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/11336/8157
Gola, Gabriel; Gallo, Carola; Synthesis of alpha-D-Glcp-(1-3)-alpha-D-Galf-(1-2)-alpha-L-Rhap constituent of the CPS of Streptococcus pneumoniae 22F. Effect of 3-O-substitution in 1,2-cis alpha-D-galactofuranosylation; Royal Society of Chemistry; RSC Advances; 4; 7; 1-2014; 3368-3382
2046-2069
url http://hdl.handle.net/11336/8157
identifier_str_mv Gola, Gabriel; Gallo, Carola; Synthesis of alpha-D-Glcp-(1-3)-alpha-D-Galf-(1-2)-alpha-L-Rhap constituent of the CPS of Streptococcus pneumoniae 22F. Effect of 3-O-substitution in 1,2-cis alpha-D-galactofuranosylation; Royal Society of Chemistry; RSC Advances; 4; 7; 1-2014; 3368-3382
2046-2069
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2014/RA/C3RA45658G#!divAbstract
info:eu-repo/semantics/altIdentifier/doi/10.1039/C3RA45658G
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 Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
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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score 13.22299

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