Oligonucleotide cyclization: The thiol-maleimide reaction revisited

A novel method to synthesize cyclic oligonucleotides (5- to 26-mer) using the thiol-maleimide reaction is described. The target molecules were obtained after subsequent removal of thiol and maleimide protecting groups from 5′-maleimido-3′-thiol-derivatized linear precursors. Retro-Diels-Alder condit...

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Authors: Sánchez-Moya, Albert, Pedroso Muller, Enrique, Grandas Sagarra, Anna
Format: article
Status:Versión aceptada para publicación
Publication Date:2013
Country:España
Institution:Universidad de Barcelona
Repository:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/50383
Online Access:https://hdl.handle.net/2445/50383
Access Level:Open access
Keyword:Bioquímica
Àcids nucleics
Bacteris
Microbiologia
Ciclització (Química)
Biochemistry
Nucleic acids
Bacteria
Microbiology
Ring formation (Chemistry)
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spelling Oligonucleotide cyclization: The thiol-maleimide reaction revisitedSánchez-Moya, AlbertPedroso Muller, EnriqueGrandas Sagarra, AnnaBioquímicaÀcids nucleicsBacterisMicrobiologiaCiclització (Química)BiochemistryNucleic acidsBacteriaMicrobiologyRing formation (Chemistry)A novel method to synthesize cyclic oligonucleotides (5- to 26-mer) using the thiol-maleimide reaction is described. The target molecules were obtained after subsequent removal of thiol and maleimide protecting groups from 5′-maleimido-3′-thiol-derivatized linear precursors. Retro-Diels-Alder conditions deprotecting the maleimide simultaneously promoted cyclization cleanly and in high yield.Royal Society of Chemistry2013info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttps://hdl.handle.net/2445/50383Articles publicats en revistes (Química Inorgànica i Orgànica)reponame:Dipòsit Digital de la UBinstname:Universidad de BarcelonaInglésVersió postprint del document publicat a: http://dx.doi.org/ 10.1039/C2CC35357AChemical Communications, 2013, vol. 49, p. 309-311http://dx.doi.org/10.1039/C2CC35357A(c) Sánchez, Albert et al., 2013info:eu-repo/semantics/openAccessoai:diposit.ub.edu:2445/503832026-05-27T06:46:51Z
dc.title.none.fl_str_mv Oligonucleotide cyclization: The thiol-maleimide reaction revisited
title Oligonucleotide cyclization: The thiol-maleimide reaction revisited
spellingShingle Oligonucleotide cyclization: The thiol-maleimide reaction revisited
Sánchez-Moya, Albert
Bioquímica
Àcids nucleics
Bacteris
Microbiologia
Ciclització (Química)
Biochemistry
Nucleic acids
Bacteria
Microbiology
Ring formation (Chemistry)
title_short Oligonucleotide cyclization: The thiol-maleimide reaction revisited
title_full Oligonucleotide cyclization: The thiol-maleimide reaction revisited
title_fullStr Oligonucleotide cyclization: The thiol-maleimide reaction revisited
title_full_unstemmed Oligonucleotide cyclization: The thiol-maleimide reaction revisited
title_sort Oligonucleotide cyclization: The thiol-maleimide reaction revisited
dc.creator.none.fl_str_mv Sánchez-Moya, Albert
Pedroso Muller, Enrique
Grandas Sagarra, Anna
author Sánchez-Moya, Albert
author_facet Sánchez-Moya, Albert
Pedroso Muller, Enrique
Grandas Sagarra, Anna
author_role author
author2 Pedroso Muller, Enrique
Grandas Sagarra, Anna
author2_role author
author
dc.subject.none.fl_str_mv Bioquímica
Àcids nucleics
Bacteris
Microbiologia
Ciclització (Química)
Biochemistry
Nucleic acids
Bacteria
Microbiology
Ring formation (Chemistry)
topic Bioquímica
Àcids nucleics
Bacteris
Microbiologia
Ciclització (Química)
Biochemistry
Nucleic acids
Bacteria
Microbiology
Ring formation (Chemistry)
description A novel method to synthesize cyclic oligonucleotides (5- to 26-mer) using the thiol-maleimide reaction is described. The target molecules were obtained after subsequent removal of thiol and maleimide protecting groups from 5′-maleimido-3′-thiol-derivatized linear precursors. Retro-Diels-Alder conditions deprotecting the maleimide simultaneously promoted cyclization cleanly and in high yield.
publishDate 2013
dc.date.none.fl_str_mv 2013
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/50383
url https://hdl.handle.net/2445/50383
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Versió postprint del document publicat a: http://dx.doi.org/ 10.1039/C2CC35357A
Chemical Communications, 2013, vol. 49, p. 309-311
http://dx.doi.org/10.1039/C2CC35357A
dc.rights.none.fl_str_mv (c) Sánchez, Albert et al., 2013
info:eu-repo/semantics/openAccess
rights_invalid_str_mv (c) Sánchez, Albert et al., 2013
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 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 Articles publicats en revistes (Química Inorgànica i Orgànica)
reponame:Dipòsit Digital de la UB
instname:Universidad de Barcelona
instname_str Universidad de Barcelona
reponame_str Dipòsit Digital de la UB
collection Dipòsit Digital de la UB
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,300719

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