Immobilized enzyme reactors based on nucleoside phosphorylases and 2′-deoxyribosyltransferase for the in-flow synthesis of pharmaceutically relevant nucleoside analogues

In this work, a mono- and a bi-enzymatic analytical immobilized enzyme reactors (IMERs) were developed as prototypes for biosynthetic purposes and their performances in the in-flow synthesis of nucleoside analogues of pharmaceutical interest were evaluated. Two biocatalytic routes based on nucleosid...

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Autores:
Rinaldia, Francesca
Fernández-Lucas, Jesús
de la Fuente, Diego
Zheng, Changping
Teodora Bavaro
BAVARO, TEODORA
Peters, Benjamin
MASSOLINI, GABRIELLA
Contig, Paola
de la Mata, Isabel
TERRENI, MARCO
Calleri, Enrica
Tipo de recurso:
http://purl.org/coar/resource_type/c_816b
Fecha de publicación:
2020
Institución:
Corporación Universidad de la Costa
Repositorio:
REDICUC - Repositorio CUC
Idioma:
eng
OAI Identifier:
oai:repositorio.cuc.edu.co:11323/6247
Acceso en línea:
https://hdl.handle.net/11323/6247
https://doi.org/10.1016/j.biortech.2020.123258
https://repositorio.cuc.edu.co/
Palabra clave:
Biocatalysis
Immobilized enzyme reactors
Nucleoside analogues
Nucleoside 2′-deoxyribosyltransferases
Nucleoside phosphorylases
Rights
openAccess
License
CC0 1.0 Universal
id RCUC2_6031077eba81cbce684638fdeae1d24e
oai_identifier_str oai:repositorio.cuc.edu.co:11323/6247
network_acronym_str RCUC2
network_name_str REDICUC - Repositorio CUC
repository_id_str
dc.title.spa.fl_str_mv Immobilized enzyme reactors based on nucleoside phosphorylases and 2′-deoxyribosyltransferase for the in-flow synthesis of pharmaceutically relevant nucleoside analogues
title Immobilized enzyme reactors based on nucleoside phosphorylases and 2′-deoxyribosyltransferase for the in-flow synthesis of pharmaceutically relevant nucleoside analogues
spellingShingle Immobilized enzyme reactors based on nucleoside phosphorylases and 2′-deoxyribosyltransferase for the in-flow synthesis of pharmaceutically relevant nucleoside analogues
Biocatalysis
Immobilized enzyme reactors
Nucleoside analogues
Nucleoside 2′-deoxyribosyltransferases
Nucleoside phosphorylases
title_short Immobilized enzyme reactors based on nucleoside phosphorylases and 2′-deoxyribosyltransferase for the in-flow synthesis of pharmaceutically relevant nucleoside analogues
title_full Immobilized enzyme reactors based on nucleoside phosphorylases and 2′-deoxyribosyltransferase for the in-flow synthesis of pharmaceutically relevant nucleoside analogues
title_fullStr Immobilized enzyme reactors based on nucleoside phosphorylases and 2′-deoxyribosyltransferase for the in-flow synthesis of pharmaceutically relevant nucleoside analogues
title_full_unstemmed Immobilized enzyme reactors based on nucleoside phosphorylases and 2′-deoxyribosyltransferase for the in-flow synthesis of pharmaceutically relevant nucleoside analogues
title_sort Immobilized enzyme reactors based on nucleoside phosphorylases and 2′-deoxyribosyltransferase for the in-flow synthesis of pharmaceutically relevant nucleoside analogues
dc.creator.fl_str_mv Rinaldia, Francesca
Fernández-Lucas, Jesús
de la Fuente, Diego
Zheng, Changping
Teodora Bavaro
BAVARO, TEODORA
Peters, Benjamin
MASSOLINI, GABRIELLA
Contig, Paola
de la Mata, Isabel
TERRENI, MARCO
Calleri, Enrica
dc.contributor.author.spa.fl_str_mv Rinaldia, Francesca
Fernández-Lucas, Jesús
de la Fuente, Diego
Zheng, Changping
Teodora Bavaro
BAVARO, TEODORA
Peters, Benjamin
MASSOLINI, GABRIELLA
Contig, Paola
de la Mata, Isabel
TERRENI, MARCO
Calleri, Enrica
dc.subject.spa.fl_str_mv Biocatalysis
Immobilized enzyme reactors
Nucleoside analogues
Nucleoside 2′-deoxyribosyltransferases
Nucleoside phosphorylases
topic Biocatalysis
Immobilized enzyme reactors
Nucleoside analogues
Nucleoside 2′-deoxyribosyltransferases
Nucleoside phosphorylases
description In this work, a mono- and a bi-enzymatic analytical immobilized enzyme reactors (IMERs) were developed as prototypes for biosynthetic purposes and their performances in the in-flow synthesis of nucleoside analogues of pharmaceutical interest were evaluated. Two biocatalytic routes based on nucleoside 2′-deoxyribosyltransferase from Lactobacillus reuteri (LrNDT) and uridine phosphorylase from Clostridium perfrigens (CpUP)/purine nucleoside phosphorylase from Aeromonas hydrophila (AhPNP) were investigated in the synthesis of 2′-deoxy, 2′,3′-dideoxy and arabinonucleoside derivatives. LrNDT-IMER catalyzed the synthesis of 5-fluoro-2′-deoxyuridine and 5-iodo-2′-deoxyuridine in 65–59% conversion yield, while CpUP/AhPNP-IMER provided the best results for the preparation of arabinosyladenine (60% conversion yield). Both IMERs proved to be promising alternatives to chemical routes for the synthesis of nucleoside analogues. The developed in-flow system represents a powerful tool for the fast production on analytical scale of nucleosides for preliminary biological tests.
publishDate 2020
dc.date.accessioned.none.fl_str_mv 2020-05-04T22:11:33Z
dc.date.available.none.fl_str_mv 2020-05-04T22:11:33Z
dc.date.issued.none.fl_str_mv 2020
dc.type.spa.fl_str_mv Pre-Publicación
dc.type.coar.spa.fl_str_mv http://purl.org/coar/resource_type/c_816b
dc.type.content.spa.fl_str_mv Text
dc.type.driver.spa.fl_str_mv info:eu-repo/semantics/preprint
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dc.type.version.spa.fl_str_mv info:eu-repo/semantics/acceptedVersion
format http://purl.org/coar/resource_type/c_816b
status_str acceptedVersion
dc.identifier.uri.spa.fl_str_mv https://hdl.handle.net/11323/6247
dc.identifier.doi.spa.fl_str_mv https://doi.org/10.1016/j.biortech.2020.123258
dc.identifier.instname.spa.fl_str_mv Corporación Universidad de la Costa
dc.identifier.reponame.spa.fl_str_mv REDICUC - Repositorio CUC
dc.identifier.repourl.spa.fl_str_mv https://repositorio.cuc.edu.co/
url https://hdl.handle.net/11323/6247
https://doi.org/10.1016/j.biortech.2020.123258
https://repositorio.cuc.edu.co/
identifier_str_mv Corporación Universidad de la Costa
REDICUC - Repositorio CUC
dc.language.iso.none.fl_str_mv eng
language eng
dc.rights.spa.fl_str_mv CC0 1.0 Universal
dc.rights.uri.spa.fl_str_mv http://creativecommons.org/publicdomain/zero/1.0/
dc.rights.accessrights.spa.fl_str_mv info:eu-repo/semantics/openAccess
dc.rights.coar.spa.fl_str_mv http://purl.org/coar/access_right/c_abf2
rights_invalid_str_mv CC0 1.0 Universal
http://creativecommons.org/publicdomain/zero/1.0/
http://purl.org/coar/access_right/c_abf2
eu_rights_str_mv openAccess
dc.publisher.spa.fl_str_mv Universidad de la Costa
institution Corporación Universidad de la Costa
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spelling Rinaldia, FrancescaFernández-Lucas, Jesúsde la Fuente, DiegoZheng, ChangpingTeodora BavaroBAVARO, TEODORAPeters, BenjaminMASSOLINI, GABRIELLAContig, Paolade la Mata, IsabelTERRENI, MARCOCalleri, Enrica2020-05-04T22:11:33Z2020-05-04T22:11:33Z2020https://hdl.handle.net/11323/6247https://doi.org/10.1016/j.biortech.2020.123258Corporación Universidad de la CostaREDICUC - Repositorio CUChttps://repositorio.cuc.edu.co/In this work, a mono- and a bi-enzymatic analytical immobilized enzyme reactors (IMERs) were developed as prototypes for biosynthetic purposes and their performances in the in-flow synthesis of nucleoside analogues of pharmaceutical interest were evaluated. Two biocatalytic routes based on nucleoside 2′-deoxyribosyltransferase from Lactobacillus reuteri (LrNDT) and uridine phosphorylase from Clostridium perfrigens (CpUP)/purine nucleoside phosphorylase from Aeromonas hydrophila (AhPNP) were investigated in the synthesis of 2′-deoxy, 2′,3′-dideoxy and arabinonucleoside derivatives. LrNDT-IMER catalyzed the synthesis of 5-fluoro-2′-deoxyuridine and 5-iodo-2′-deoxyuridine in 65–59% conversion yield, while CpUP/AhPNP-IMER provided the best results for the preparation of arabinosyladenine (60% conversion yield). Both IMERs proved to be promising alternatives to chemical routes for the synthesis of nucleoside analogues. The developed in-flow system represents a powerful tool for the fast production on analytical scale of nucleosides for preliminary biological tests.Rinaldia, FrancescaFernández-Lucas, Jesús-will be generated-orcid-0000-0001-7045-8306-600de la Fuente, Diego-will be generated-orcid-0000-0002-6193-7345-600Zheng, ChangpingTeodora BavaroBAVARO, TEODORA-will be generated-orcid-0000-0002-1286-2535-600Peters, BenjaminMASSOLINI, GABRIELLA-will be generated-orcid-0000-0003-3035-9076-600Contig, Paolade la Mata, Isabel-will be generated-orcid-0000-0002-6637-2451-600TERRENI, MARCO-will be generated-orcid-0000-0002-7470-513X-600Calleri, EnricaengUniversidad de la CostaCC0 1.0 Universalhttp://creativecommons.org/publicdomain/zero/1.0/info:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2BiocatalysisImmobilized enzyme reactorsNucleoside analoguesNucleoside 2′-deoxyribosyltransferasesNucleoside phosphorylasesImmobilized enzyme reactors based on nucleoside phosphorylases and 2′-deoxyribosyltransferase for the in-flow synthesis of pharmaceutically relevant nucleoside analoguesPre-Publicaciónhttp://purl.org/coar/resource_type/c_816bTextinfo:eu-repo/semantics/preprinthttp://purl.org/redcol/resource_type/ARTOTRinfo:eu-repo/semantics/acceptedVersionPublicationORIGINALImmobilized enzyme reactors based on nucleoside phosphorylases and 2′-deoxyribosyltransferase for the in-flow synthesis of pharmaceutically relevant nucleoside analogues.pdfImmobilized enzyme reactors based on nucleoside phosphorylases and 2′-deoxyribosyltransferase for the in-flow synthesis of pharmaceutically relevant nucleoside analogues.pdfapplication/pdf293288https://repositorio.cuc.edu.co/bitstreams/20dddbe6-6b32-4277-b543-8166c0b588cd/download2eef4cd6afa094b6cb9760e2b4752e2fMD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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