Synthesis of γ-Hydroxy-α-amino Acid Derivatives by Enzymatic Tandem Aldol Addition-Transamination Reactions

Three enzymatic routes toward γ-hydroxy-α-amino acids by tandem aldol addition-transamination one-pot two-step reactions are reported. The approaches feature an enantioselective aldol addition of pyruvate to various nonaromatic aldehydes catalyzed by trans - o -hydroxybenzylidene pyruvate hydratase-...

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Autores: Moreno, Carlos J., Hernández, Karel|||0000-0001-7367-4426, Charnok, Simon J., Gittings, Samantha, Bolte, Michael|||0000-0001-5296-6251, Joglar, Jesús|||0000-0002-3391-1682, Bujons, Jordi|||0000-0003-2944-2905, Parella Coll, Teodor|||0000-0002-1914-2709, Clapés, Pere|||0000-0001-5541-4794
Formato: artículo
Fecha de publicación:2021
País:España
Recursos:Universitat Autònoma de Barcelona
Repositorio:Dipòsit Digital de Documents de la UAB
Idioma:inglés
OAI Identifier:oai:ddd.uab.cat:250459
Acesso em linha:https://ddd.uab.cat/record/250459
https://dx.doi.org/urn:doi:10.1021/acscatal.1c00210
Access Level:acceso abierto
Palavra-chave:Biocatalysis
2-oxoacid aldolase
Transaminases
Aldol addition
Reductive amination
Γ-hydroxy-α-amino acids
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spelling Synthesis of γ-Hydroxy-α-amino Acid Derivatives by Enzymatic Tandem Aldol Addition-Transamination ReactionsMoreno, Carlos J.Hernández, Karel|||0000-0001-7367-4426Charnok, Simon J.Gittings, SamanthaBolte, Michael|||0000-0001-5296-6251Joglar, Jesús|||0000-0002-3391-1682Bujons, Jordi|||0000-0003-2944-2905Parella Coll, Teodor|||0000-0002-1914-2709Clapés, Pere|||0000-0001-5541-4794Biocatalysis2-oxoacid aldolaseTransaminasesAldol additionReductive aminationΓ-hydroxy-α-amino acidsThree enzymatic routes toward γ-hydroxy-α-amino acids by tandem aldol addition-transamination one-pot two-step reactions are reported. The approaches feature an enantioselective aldol addition of pyruvate to various nonaromatic aldehydes catalyzed by trans - o -hydroxybenzylidene pyruvate hydratase-aldolase (HBPA) from Pseudomonas putida. This affords chiral 4-hydroxy-2-oxo acids, which were subsequently enantioselectively aminated using S -selective transaminases. Three transamination processes were investigated involving different amine donors and transaminases: (i) -Ala as an amine donor with pyruvate recycling, (ii) a benzylamine donor using benzaldehyde lyase from Pseudomonas fluorescens Biovar I (BAL) to transform the benzaldehyde formed into benzoin, minimizing equilibrium limitations, and (iii) -Glu as an amine donor with a double cascade comprising branched-chain α-amino acid aminotransferase (BCAT) and aspartate amino transferase (AspAT), both from E. coli, using -Asp as a substrate to regenerate -Glu. The γ-hydroxy-α-amino acids thus obtained were transformed into chiral α-amino-γ-butyrolactones, structural motifs found in many biologically active compounds and valuable intermediates for the synthesis of pharmaceutical agents. 22021-01-0120212021-01-01Articlehttp://purl.org/coar/resource_type/c_6501VoRhttp://purl.org/coar/version/c_970fb48d4fbd8a85info:eu-repo/semantics/articleapplication/pdfhttps://ddd.uab.cat/record/250459https://dx.doi.org/urn:doi:10.1021/acscatal.1c00210reponame:Dipòsit Digital de Documents de la UABinstname:Universitat Autònoma de BarcelonaInglésengAgencia Estatal de Investigación https://doi.org/10.13039/501100011033 RTI2018-094637-B-I00Agencia Estatal de Investigación https://doi.org/10.13039/501100011033 PGC2018-095808-B-I00Agencia Estatal de Investigación https://doi.org/10.13039/501100011033 PCI2018-092937European Commission https://doi.org/10.13039/501100000780 722361open accesshttp://purl.org/coar/access_right/c_abf2Aquest document està subjecte a una llicència d'ús Creative Commons. Es permet la reproducció total o parcial, la distribució, la comunicació pública de l'obra i la creació d'obres derivades, fins i tot amb finalitats comercials, sempre i quan es reconegui l'autoria de l'obra original.https://creativecommons.org/licenses/by/4.0/info:eu-repo/semantics/openAccessoai:ddd.uab.cat:2504592026-06-06T12:50:31Z
dc.title.none.fl_str_mv Synthesis of γ-Hydroxy-α-amino Acid Derivatives by Enzymatic Tandem Aldol Addition-Transamination Reactions
title Synthesis of γ-Hydroxy-α-amino Acid Derivatives by Enzymatic Tandem Aldol Addition-Transamination Reactions
spellingShingle Synthesis of γ-Hydroxy-α-amino Acid Derivatives by Enzymatic Tandem Aldol Addition-Transamination Reactions
Moreno, Carlos J.
Biocatalysis
2-oxoacid aldolase
Transaminases
Aldol addition
Reductive amination
Γ-hydroxy-α-amino acids
title_short Synthesis of γ-Hydroxy-α-amino Acid Derivatives by Enzymatic Tandem Aldol Addition-Transamination Reactions
title_full Synthesis of γ-Hydroxy-α-amino Acid Derivatives by Enzymatic Tandem Aldol Addition-Transamination Reactions
title_fullStr Synthesis of γ-Hydroxy-α-amino Acid Derivatives by Enzymatic Tandem Aldol Addition-Transamination Reactions
title_full_unstemmed Synthesis of γ-Hydroxy-α-amino Acid Derivatives by Enzymatic Tandem Aldol Addition-Transamination Reactions
title_sort Synthesis of γ-Hydroxy-α-amino Acid Derivatives by Enzymatic Tandem Aldol Addition-Transamination Reactions
dc.creator.none.fl_str_mv Moreno, Carlos J.
Hernández, Karel|||0000-0001-7367-4426
Charnok, Simon J.
Gittings, Samantha
Bolte, Michael|||0000-0001-5296-6251
Joglar, Jesús|||0000-0002-3391-1682
Bujons, Jordi|||0000-0003-2944-2905
Parella Coll, Teodor|||0000-0002-1914-2709
Clapés, Pere|||0000-0001-5541-4794
author Moreno, Carlos J.
author_facet Moreno, Carlos J.
Hernández, Karel|||0000-0001-7367-4426
Charnok, Simon J.
Gittings, Samantha
Bolte, Michael|||0000-0001-5296-6251
Joglar, Jesús|||0000-0002-3391-1682
Bujons, Jordi|||0000-0003-2944-2905
Parella Coll, Teodor|||0000-0002-1914-2709
Clapés, Pere|||0000-0001-5541-4794
author_role author
author2 Hernández, Karel|||0000-0001-7367-4426
Charnok, Simon J.
Gittings, Samantha
Bolte, Michael|||0000-0001-5296-6251
Joglar, Jesús|||0000-0002-3391-1682
Bujons, Jordi|||0000-0003-2944-2905
Parella Coll, Teodor|||0000-0002-1914-2709
Clapés, Pere|||0000-0001-5541-4794
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Biocatalysis
2-oxoacid aldolase
Transaminases
Aldol addition
Reductive amination
Γ-hydroxy-α-amino acids
topic Biocatalysis
2-oxoacid aldolase
Transaminases
Aldol addition
Reductive amination
Γ-hydroxy-α-amino acids
description Three enzymatic routes toward γ-hydroxy-α-amino acids by tandem aldol addition-transamination one-pot two-step reactions are reported. The approaches feature an enantioselective aldol addition of pyruvate to various nonaromatic aldehydes catalyzed by trans - o -hydroxybenzylidene pyruvate hydratase-aldolase (HBPA) from Pseudomonas putida. This affords chiral 4-hydroxy-2-oxo acids, which were subsequently enantioselectively aminated using S -selective transaminases. Three transamination processes were investigated involving different amine donors and transaminases: (i) -Ala as an amine donor with pyruvate recycling, (ii) a benzylamine donor using benzaldehyde lyase from Pseudomonas fluorescens Biovar I (BAL) to transform the benzaldehyde formed into benzoin, minimizing equilibrium limitations, and (iii) -Glu as an amine donor with a double cascade comprising branched-chain α-amino acid aminotransferase (BCAT) and aspartate amino transferase (AspAT), both from E. coli, using -Asp as a substrate to regenerate -Glu. The γ-hydroxy-α-amino acids thus obtained were transformed into chiral α-amino-γ-butyrolactones, structural motifs found in many biologically active compounds and valuable intermediates for the synthesis of pharmaceutical agents.
publishDate 2021
dc.date.none.fl_str_mv 2
2021-01-01
2021
2021-01-01
dc.type.none.fl_str_mv Article
http://purl.org/coar/resource_type/c_6501
VoR
http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv https://ddd.uab.cat/record/250459
https://dx.doi.org/urn:doi:10.1021/acscatal.1c00210
url https://ddd.uab.cat/record/250459
https://dx.doi.org/urn:doi:10.1021/acscatal.1c00210
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.relation.none.fl_str_mv Agencia Estatal de Investigación https://doi.org/10.13039/501100011033 RTI2018-094637-B-I00
Agencia Estatal de Investigación https://doi.org/10.13039/501100011033 PGC2018-095808-B-I00
Agencia Estatal de Investigación https://doi.org/10.13039/501100011033 PCI2018-092937
European Commission https://doi.org/10.13039/501100000780 722361
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
https://creativecommons.org/licenses/by/4.0/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
https://creativecommons.org/licenses/by/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:Dipòsit Digital de Documents de la UAB
instname:Universitat Autònoma de Barcelona
instname_str Universitat Autònoma de Barcelona
reponame_str Dipòsit Digital de Documents de la UAB
collection Dipòsit Digital de Documents de la UAB
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,223283

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