Improved synthesis of phytanyl α-D-cellobiosyldiphosphate as substrate for α-D-mannosyltransferase

Autores
Barrios, Pablo Daniel; Ielpi, Luis; Marino, Carla
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Polyisoprenyl-pyrophosphate-linked cellobiose is the natural acceptor of the α-1,3- mannosyltransferase AceA from Acetobacter xylinum, which transfers mannose from GDPmannose during the assembly of the heptasaccharide repeat unit of the exopolysaccharide acetan. Phytanyl α-D-cellobiosyldiphosphate 4 has been previously synthesized as an analogue acceptor by condensation of hepta-O-acetyl-α-D-cellobiosylphosphate 1 with phytanylphosphate 2, but the procedure was briefly described. We report here a modified detailed synthesis of 4. The complete NMR characterization of 4 is provided and also a selection of NMR signals of all the intermediate compounds which facilitate monitoring the synthesis.
Fil: Barrios, Pablo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Ielpi, Luis. Fundación Instituto Leloir; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Parque Centenario. Instituto de Investigaciones Bioquimicas de Buenos Aires; Argentina
Fil: Marino, Carla. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Materia
Mannosyltransferase
glycosyl phosphate
phytanyl phosphate
Acetobacter xylinium
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/12696
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Improved synthesis of phytanyl α-D-cellobiosyldiphosphate as substrate for α-D-mannosyltransferaseBarrios, Pablo DanielIelpi, LuisMarino, CarlaMannosyltransferaseglycosyl phosphatephytanyl phosphateAcetobacter xyliniumhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Polyisoprenyl-pyrophosphate-linked cellobiose is the natural acceptor of the α-1,3- mannosyltransferase AceA from Acetobacter xylinum, which transfers mannose from GDPmannose during the assembly of the heptasaccharide repeat unit of the exopolysaccharide acetan. Phytanyl α-D-cellobiosyldiphosphate 4 has been previously synthesized as an analogue acceptor by condensation of hepta-O-acetyl-α-D-cellobiosylphosphate 1 with phytanylphosphate 2, but the procedure was briefly described. We report here a modified detailed synthesis of 4. The complete NMR characterization of 4 is provided and also a selection of NMR signals of all the intermediate compounds which facilitate monitoring the synthesis.Fil: Barrios, Pablo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaFil: Ielpi, Luis. Fundación Instituto Leloir; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Parque Centenario. Instituto de Investigaciones Bioquimicas de Buenos Aires; ArgentinaFil: Marino, Carla. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaArkat Usa2011-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/12696Barrios, Pablo Daniel; Ielpi, Luis; Marino, Carla; Improved synthesis of phytanyl α-D-cellobiosyldiphosphate as substrate for α-D-mannosyltransferase; Arkat Usa; Arkivoc - Archive For Organic Chemistry; 2011; 7; 1-2011; 38-481551-7004enginfo:eu-repo/semantics/altIdentifier/url/http://quod.lib.umich.edu/a/ark/5550190.0012.707/1info:eu-repo/semantics/altIdentifier/doi/10.3998/ark.5550190.0012.707info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:58:03Zoai:ri.conicet.gov.ar:11336/12696instacron: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 09:58:03.907CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Improved synthesis of phytanyl α-D-cellobiosyldiphosphate as substrate for α-D-mannosyltransferase
title Improved synthesis of phytanyl α-D-cellobiosyldiphosphate as substrate for α-D-mannosyltransferase
spellingShingle Improved synthesis of phytanyl α-D-cellobiosyldiphosphate as substrate for α-D-mannosyltransferase
Barrios, Pablo Daniel
Mannosyltransferase
glycosyl phosphate
phytanyl phosphate
Acetobacter xylinium
title_short Improved synthesis of phytanyl α-D-cellobiosyldiphosphate as substrate for α-D-mannosyltransferase
title_full Improved synthesis of phytanyl α-D-cellobiosyldiphosphate as substrate for α-D-mannosyltransferase
title_fullStr Improved synthesis of phytanyl α-D-cellobiosyldiphosphate as substrate for α-D-mannosyltransferase
title_full_unstemmed Improved synthesis of phytanyl α-D-cellobiosyldiphosphate as substrate for α-D-mannosyltransferase
title_sort Improved synthesis of phytanyl α-D-cellobiosyldiphosphate as substrate for α-D-mannosyltransferase
dc.creator.none.fl_str_mv Barrios, Pablo Daniel
Ielpi, Luis
Marino, Carla
author Barrios, Pablo Daniel
author_facet Barrios, Pablo Daniel
Ielpi, Luis
Marino, Carla
author_role author
author2 Ielpi, Luis
Marino, Carla
author2_role author
author
dc.subject.none.fl_str_mv Mannosyltransferase
glycosyl phosphate
phytanyl phosphate
Acetobacter xylinium
topic Mannosyltransferase
glycosyl phosphate
phytanyl phosphate
Acetobacter xylinium
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Polyisoprenyl-pyrophosphate-linked cellobiose is the natural acceptor of the α-1,3- mannosyltransferase AceA from Acetobacter xylinum, which transfers mannose from GDPmannose during the assembly of the heptasaccharide repeat unit of the exopolysaccharide acetan. Phytanyl α-D-cellobiosyldiphosphate 4 has been previously synthesized as an analogue acceptor by condensation of hepta-O-acetyl-α-D-cellobiosylphosphate 1 with phytanylphosphate 2, but the procedure was briefly described. We report here a modified detailed synthesis of 4. The complete NMR characterization of 4 is provided and also a selection of NMR signals of all the intermediate compounds which facilitate monitoring the synthesis.
Fil: Barrios, Pablo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Ielpi, Luis. Fundación Instituto Leloir; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Parque Centenario. Instituto de Investigaciones Bioquimicas de Buenos Aires; Argentina
Fil: Marino, Carla. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
description Polyisoprenyl-pyrophosphate-linked cellobiose is the natural acceptor of the α-1,3- mannosyltransferase AceA from Acetobacter xylinum, which transfers mannose from GDPmannose during the assembly of the heptasaccharide repeat unit of the exopolysaccharide acetan. Phytanyl α-D-cellobiosyldiphosphate 4 has been previously synthesized as an analogue acceptor by condensation of hepta-O-acetyl-α-D-cellobiosylphosphate 1 with phytanylphosphate 2, but the procedure was briefly described. We report here a modified detailed synthesis of 4. The complete NMR characterization of 4 is provided and also a selection of NMR signals of all the intermediate compounds which facilitate monitoring the synthesis.
publishDate 2011
dc.date.none.fl_str_mv 2011-01
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/11336/12696
Barrios, Pablo Daniel; Ielpi, Luis; Marino, Carla; Improved synthesis of phytanyl α-D-cellobiosyldiphosphate as substrate for α-D-mannosyltransferase; Arkat Usa; Arkivoc - Archive For Organic Chemistry; 2011; 7; 1-2011; 38-48
1551-7004
url http://hdl.handle.net/11336/12696
identifier_str_mv Barrios, Pablo Daniel; Ielpi, Luis; Marino, Carla; Improved synthesis of phytanyl α-D-cellobiosyldiphosphate as substrate for α-D-mannosyltransferase; Arkat Usa; Arkivoc - Archive For Organic Chemistry; 2011; 7; 1-2011; 38-48
1551-7004
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://quod.lib.umich.edu/a/ark/5550190.0012.707/1
info:eu-repo/semantics/altIdentifier/doi/10.3998/ark.5550190.0012.707
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Arkat Usa
publisher.none.fl_str_mv Arkat Usa
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_ 1844613733045764096
score 13.070432

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