Kinetic Studies of Acetyl Group Migration between the Saccharide Units in an Oligomannoside Trisaccharide Model Compound and a Native Galactoglucomannan Polysaccharide

Acyl group migration is a fundamental phenomenon in carbohydrate chemistry, recently shown to take place also between two non-adjacent hydroxyl groups, across the glycosidic bond, in a beta-(1 -> 4)-linked mannan trisaccharide model compound. With the central mannoside unit containing acetyl grou...

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Autores: Lassfolk, Robert, Bertuzzi, Sara, Ardá, Ana, Warna, Johan, Jiménez Barbero, Jesús, Leino, Reko
Tipo de recurso: artículo
Fecha de publicación:2021
País:España
Institución:Universidad del País Vasco
Repositorio:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/53526
Acceso en línea:http://hdl.handle.net/10810/53526
Access Level:acceso abierto
Palabra clave:acyl migration
C-type lectin
carbohydrates
DC-SIGN
galactoglucomannan
ligand-binding
norway spruce
structural features
NMR-spectroscopy
cell-walls
PH
oligosaccharides
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spelling Kinetic Studies of Acetyl Group Migration between the Saccharide Units in an Oligomannoside Trisaccharide Model Compound and a Native Galactoglucomannan PolysaccharideLassfolk, RobertBertuzzi, SaraArdá, AnaWarna, JohanJiménez Barbero, JesúsLeino, Rekoacyl migrationC-type lectincarbohydratesDC-SIGNgalactoglucomannanligand-bindingnorway sprucestructural featuresNMR-spectroscopycell-wallsPHoligosaccharidesAcyl group migration is a fundamental phenomenon in carbohydrate chemistry, recently shown to take place also between two non-adjacent hydroxyl groups, across the glycosidic bond, in a beta-(1 -> 4)-linked mannan trisaccharide model compound. With the central mannoside unit containing acetyl groups at the O2 and O3 positions, the O2-acetyl was in the earlier study shown to migrate to O6 of the reducing end. Potential implications of the general acyl migration process on cell signaling events and plant growth in nature are intriguing open questions. In the present work, migration kinetics in this original trisaccharide model system were studied in more detail together with potential interactions of the model compound and the migration products with DC-SIGN lectin. Furthermore, we demonstrate here for the first time that similar migration may also take place in native polysaccharides, here represented by galactoglucomannan from Norway spruce.The authors acknowledge the European Research Council for financial support (ERC-2017-AdG, project number 788143-RECGLYCA NMR) and the Agencia Estatal de Investigacion (Spain) for project RTI2018-094751-B-C21 (to JJB)WileyEuropean Commission202120212021info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10810/53526reponame:Addi. Archivo Digital para la Docencia y la Investigacióninstname:Universidad del País VascoInglésinfo:eu-repo/grantAgreement/EC/H2020/788143info:eu-repo/grantAgreement/MICINN/RTI2018-094751-B-C21/https://chemistry-europe-onlinelibrary-wiley-com.ehu.idm.oclc.org/doi/10.1002/cbic.202100374info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/3.0/es/This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY 4.0)Atribución 3.0 Españaoai:addi.ehu.eus:10810/535262026-06-18T09:23:17Z
dc.title.none.fl_str_mv Kinetic Studies of Acetyl Group Migration between the Saccharide Units in an Oligomannoside Trisaccharide Model Compound and a Native Galactoglucomannan Polysaccharide
title Kinetic Studies of Acetyl Group Migration between the Saccharide Units in an Oligomannoside Trisaccharide Model Compound and a Native Galactoglucomannan Polysaccharide
spellingShingle Kinetic Studies of Acetyl Group Migration between the Saccharide Units in an Oligomannoside Trisaccharide Model Compound and a Native Galactoglucomannan Polysaccharide
Lassfolk, Robert
acyl migration
C-type lectin
carbohydrates
DC-SIGN
galactoglucomannan
ligand-binding
norway spruce
structural features
NMR-spectroscopy
cell-walls
PH
oligosaccharides
title_short Kinetic Studies of Acetyl Group Migration between the Saccharide Units in an Oligomannoside Trisaccharide Model Compound and a Native Galactoglucomannan Polysaccharide
title_full Kinetic Studies of Acetyl Group Migration between the Saccharide Units in an Oligomannoside Trisaccharide Model Compound and a Native Galactoglucomannan Polysaccharide
title_fullStr Kinetic Studies of Acetyl Group Migration between the Saccharide Units in an Oligomannoside Trisaccharide Model Compound and a Native Galactoglucomannan Polysaccharide
title_full_unstemmed Kinetic Studies of Acetyl Group Migration between the Saccharide Units in an Oligomannoside Trisaccharide Model Compound and a Native Galactoglucomannan Polysaccharide
title_sort Kinetic Studies of Acetyl Group Migration between the Saccharide Units in an Oligomannoside Trisaccharide Model Compound and a Native Galactoglucomannan Polysaccharide
dc.creator.none.fl_str_mv Lassfolk, Robert
Bertuzzi, Sara
Ardá, Ana
Warna, Johan
Jiménez Barbero, Jesús
Leino, Reko
author Lassfolk, Robert
author_facet Lassfolk, Robert
Bertuzzi, Sara
Ardá, Ana
Warna, Johan
Jiménez Barbero, Jesús
Leino, Reko
author_role author
author2 Bertuzzi, Sara
Ardá, Ana
Warna, Johan
Jiménez Barbero, Jesús
Leino, Reko
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv European Commission
dc.subject.none.fl_str_mv acyl migration
C-type lectin
carbohydrates
DC-SIGN
galactoglucomannan
ligand-binding
norway spruce
structural features
NMR-spectroscopy
cell-walls
PH
oligosaccharides
topic acyl migration
C-type lectin
carbohydrates
DC-SIGN
galactoglucomannan
ligand-binding
norway spruce
structural features
NMR-spectroscopy
cell-walls
PH
oligosaccharides
description Acyl group migration is a fundamental phenomenon in carbohydrate chemistry, recently shown to take place also between two non-adjacent hydroxyl groups, across the glycosidic bond, in a beta-(1 -> 4)-linked mannan trisaccharide model compound. With the central mannoside unit containing acetyl groups at the O2 and O3 positions, the O2-acetyl was in the earlier study shown to migrate to O6 of the reducing end. Potential implications of the general acyl migration process on cell signaling events and plant growth in nature are intriguing open questions. In the present work, migration kinetics in this original trisaccharide model system were studied in more detail together with potential interactions of the model compound and the migration products with DC-SIGN lectin. Furthermore, we demonstrate here for the first time that similar migration may also take place in native polysaccharides, here represented by galactoglucomannan from Norway spruce.
publishDate 2021
dc.date.none.fl_str_mv 2021
2021
2021
dc.type.none.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10810/53526
url http://hdl.handle.net/10810/53526
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/grantAgreement/EC/H2020/788143
info:eu-repo/grantAgreement/MICINN/RTI2018-094751-B-C21/
https://chemistry-europe-onlinelibrary-wiley-com.ehu.idm.oclc.org/doi/10.1002/cbic.202100374
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/3.0/es/
Atribución 3.0 España
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/3.0/es/
Atribución 3.0 España
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv reponame:Addi. Archivo Digital para la Docencia y la Investigación
instname:Universidad del País Vasco
instname_str Universidad del País Vasco
reponame_str Addi. Archivo Digital para la Docencia y la Investigación
collection Addi. Archivo Digital para la Docencia y la Investigación
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.301603

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