An Alternative Pathway for the Synthesis of Glycerol Phenylbutyrate

Autores
Suchetti, Laura; Foray, Gabriela; Tempesti, Tomas C.; Ferrayoli, Carlos
Año de publicación
2024
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Impact Factor: 2.1
Fil: Suchetti, Laura. Ministerio de Ciencia y Tecnología de la Provincia de Córdoba. Departamento de Química, Argentina.
Fil: Foray, Gabriela. Ministerio de Ciencia y Tecnología de la Provincia de Córdoba. Departamento de Química, Argentina.
Fil: Tempesti Tomas C. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica, Argentina.
Fil: Tempesti Tomas C. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Físico-Química de Córdoba, Argentina.
Fil: Ferrayoli, Carlos. Ministerio de Ciencia y Tecnología de la Provincia de Córdoba. Departamento de Química, Argentina.
Hyperammonemia is a life-threatening condition which can affect patients at any age. In pediatric patients, hyperammonemia can be caused by various acquired or inherited disorders such as urea cycle deficiencies or organic acidemias. Glycerol phenylbutyrate (GPB) is an orphan drug used in the treatment of hyperammonemia. GPB is a triglyceride composed of three phenylbutyric acid (PBA) molecules esterified to a glycerol molecule, which is synthesized through the acyl chloride route using thionyl chloride as an acylating agent. In this work we have developed an alternative synthesis method to obtain GPB directly under ambient conditions and avoiding the use of chlorinated solvents. Moreover, the use of carbodiimides as coupling agents, instead of thionyl chloride, allowed the conversion to the GPB in higher yields and with higher purity, without the need for column purification. We present a methodology that allows the production of GPB in a simple, efficient and environmentally and human health friendly way.
info:eu-repo/semantics/publishedVersion
Fil: Suchetti, Laura. Ministerio de Ciencia y Tecnología de la Provincia de Córdoba. Departamento de Química, Argentina.
Fil: Foray, Gabriela. Ministerio de Ciencia y Tecnología de la Provincia de Córdoba. Departamento de Química, Argentina.
Fil: Tempesti Tomas C. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica, Argentina.
Fil: Tempesti Tomas C. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Físico-Química de Córdoba, Argentina.
Fil: Ferrayoli, Carlos. Ministerio de Ciencia y Tecnología de la Provincia de Córdoba. Departamento de Química, Argentina.
Materia
Synthesis of Glycerol
Phenylbutyrate
Pediatric patients
Hyperammonemia
Nivel de accesibilidad
acceso abierto
Condiciones de uso
Repositorio
Repositorio Digital Universitario (UNC)
Institución
Universidad Nacional de Córdoba
OAI Identificador
oai:rdu.unc.edu.ar:11086/552607

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network_name_str Repositorio Digital Universitario (UNC)
spelling An Alternative Pathway for the Synthesis of Glycerol PhenylbutyrateSuchetti, LauraForay, GabrielaTempesti, Tomas C.Ferrayoli, CarlosSynthesis of GlycerolPhenylbutyratePediatric patientsHyperammonemiaImpact Factor: 2.1Fil: Suchetti, Laura. Ministerio de Ciencia y Tecnología de la Provincia de Córdoba. Departamento de Química, Argentina.Fil: Foray, Gabriela. Ministerio de Ciencia y Tecnología de la Provincia de Córdoba. Departamento de Química, Argentina.Fil: Tempesti Tomas C. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica, Argentina.Fil: Tempesti Tomas C. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Físico-Química de Córdoba, Argentina.Fil: Ferrayoli, Carlos. Ministerio de Ciencia y Tecnología de la Provincia de Córdoba. Departamento de Química, Argentina.Hyperammonemia is a life-threatening condition which can affect patients at any age. In pediatric patients, hyperammonemia can be caused by various acquired or inherited disorders such as urea cycle deficiencies or organic acidemias. Glycerol phenylbutyrate (GPB) is an orphan drug used in the treatment of hyperammonemia. GPB is a triglyceride composed of three phenylbutyric acid (PBA) molecules esterified to a glycerol molecule, which is synthesized through the acyl chloride route using thionyl chloride as an acylating agent. In this work we have developed an alternative synthesis method to obtain GPB directly under ambient conditions and avoiding the use of chlorinated solvents. Moreover, the use of carbodiimides as coupling agents, instead of thionyl chloride, allowed the conversion to the GPB in higher yields and with higher purity, without the need for column purification. We present a methodology that allows the production of GPB in a simple, efficient and environmentally and human health friendly way.info:eu-repo/semantics/publishedVersionFil: Suchetti, Laura. Ministerio de Ciencia y Tecnología de la Provincia de Córdoba. Departamento de Química, Argentina.Fil: Foray, Gabriela. Ministerio de Ciencia y Tecnología de la Provincia de Córdoba. Departamento de Química, Argentina.Fil: Tempesti Tomas C. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica, Argentina.Fil: Tempesti Tomas C. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Físico-Química de Córdoba, Argentina.Fil: Ferrayoli, Carlos. Ministerio de Ciencia y Tecnología de la Provincia de Córdoba. Departamento de Química, Argentina.https://orcid.org/0009-0006-7194-2427https://orcid.org/0000-0003-3374-22732024-01-22info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfSuchetti, L., Foray, G., Tempesti, T. C., & Ferrayoli, C. (2024). An Alternative Pathway for the Synthesis of Glycerol Phenylbutyrate. ChemistrySelect, 9(4), e202304021.http://hdl.handle.net/11086/5526072365-6549https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/slct.202304021https://chemistry-europe.onlinelibrary.wiley.com/action/downloadSupplement?doi=10.1002%2Fslct.202304021&file=slct202304021-sup-0001-misc_information.pdfhttps://doi.org/10.1002/slct.202304021enginfo:eu-repo/semantics/openAccessreponame:Repositorio Digital Universitario (UNC)instname:Universidad Nacional de Córdobainstacron:UNC2025-10-16T09:29:31Zoai:rdu.unc.edu.ar:11086/552607Institucionalhttps://rdu.unc.edu.ar/Universidad públicaNo correspondehttp://rdu.unc.edu.ar/oai/snrdoca.unc@gmail.comArgentinaNo correspondeNo correspondeNo correspondeopendoar:25722025-10-16 09:29:31.734Repositorio Digital Universitario (UNC) - Universidad Nacional de Córdobafalse
dc.title.none.fl_str_mv An Alternative Pathway for the Synthesis of Glycerol Phenylbutyrate
title An Alternative Pathway for the Synthesis of Glycerol Phenylbutyrate
spellingShingle An Alternative Pathway for the Synthesis of Glycerol Phenylbutyrate
Suchetti, Laura
Synthesis of Glycerol
Phenylbutyrate
Pediatric patients
Hyperammonemia
title_short An Alternative Pathway for the Synthesis of Glycerol Phenylbutyrate
title_full An Alternative Pathway for the Synthesis of Glycerol Phenylbutyrate
title_fullStr An Alternative Pathway for the Synthesis of Glycerol Phenylbutyrate
title_full_unstemmed An Alternative Pathway for the Synthesis of Glycerol Phenylbutyrate
title_sort An Alternative Pathway for the Synthesis of Glycerol Phenylbutyrate
dc.creator.none.fl_str_mv Suchetti, Laura
Foray, Gabriela
Tempesti, Tomas C.
Ferrayoli, Carlos
author Suchetti, Laura
author_facet Suchetti, Laura
Foray, Gabriela
Tempesti, Tomas C.
Ferrayoli, Carlos
author_role author
author2 Foray, Gabriela
Tempesti, Tomas C.
Ferrayoli, Carlos
author2_role author
author
author
dc.contributor.none.fl_str_mv https://orcid.org/0009-0006-7194-2427
https://orcid.org/0000-0003-3374-2273
dc.subject.none.fl_str_mv Synthesis of Glycerol
Phenylbutyrate
Pediatric patients
Hyperammonemia
topic Synthesis of Glycerol
Phenylbutyrate
Pediatric patients
Hyperammonemia
dc.description.none.fl_txt_mv Impact Factor: 2.1
Fil: Suchetti, Laura. Ministerio de Ciencia y Tecnología de la Provincia de Córdoba. Departamento de Química, Argentina.
Fil: Foray, Gabriela. Ministerio de Ciencia y Tecnología de la Provincia de Córdoba. Departamento de Química, Argentina.
Fil: Tempesti Tomas C. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica, Argentina.
Fil: Tempesti Tomas C. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Físico-Química de Córdoba, Argentina.
Fil: Ferrayoli, Carlos. Ministerio de Ciencia y Tecnología de la Provincia de Córdoba. Departamento de Química, Argentina.
Hyperammonemia is a life-threatening condition which can affect patients at any age. In pediatric patients, hyperammonemia can be caused by various acquired or inherited disorders such as urea cycle deficiencies or organic acidemias. Glycerol phenylbutyrate (GPB) is an orphan drug used in the treatment of hyperammonemia. GPB is a triglyceride composed of three phenylbutyric acid (PBA) molecules esterified to a glycerol molecule, which is synthesized through the acyl chloride route using thionyl chloride as an acylating agent. In this work we have developed an alternative synthesis method to obtain GPB directly under ambient conditions and avoiding the use of chlorinated solvents. Moreover, the use of carbodiimides as coupling agents, instead of thionyl chloride, allowed the conversion to the GPB in higher yields and with higher purity, without the need for column purification. We present a methodology that allows the production of GPB in a simple, efficient and environmentally and human health friendly way.
info:eu-repo/semantics/publishedVersion
Fil: Suchetti, Laura. Ministerio de Ciencia y Tecnología de la Provincia de Córdoba. Departamento de Química, Argentina.
Fil: Foray, Gabriela. Ministerio de Ciencia y Tecnología de la Provincia de Córdoba. Departamento de Química, Argentina.
Fil: Tempesti Tomas C. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica, Argentina.
Fil: Tempesti Tomas C. Consejo Nacional de Investigaciones Científicas y Técnicas. Instituto de Investigaciones en Físico-Química de Córdoba, Argentina.
Fil: Ferrayoli, Carlos. Ministerio de Ciencia y Tecnología de la Provincia de Córdoba. Departamento de Química, Argentina.
description Impact Factor: 2.1
publishDate 2024
dc.date.none.fl_str_mv 2024-01-22
dc.type.none.fl_str_mv info:eu-repo/semantics/publishedVersion
info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
status_str publishedVersion
format article
dc.identifier.none.fl_str_mv Suchetti, L., Foray, G., Tempesti, T. C., & Ferrayoli, C. (2024). An Alternative Pathway for the Synthesis of Glycerol Phenylbutyrate. ChemistrySelect, 9(4), e202304021.
http://hdl.handle.net/11086/552607
2365-6549
https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/slct.202304021
https://chemistry-europe.onlinelibrary.wiley.com/action/downloadSupplement?doi=10.1002%2Fslct.202304021&file=slct202304021-sup-0001-misc_information.pdf
https://doi.org/10.1002/slct.202304021
identifier_str_mv Suchetti, L., Foray, G., Tempesti, T. C., & Ferrayoli, C. (2024). An Alternative Pathway for the Synthesis of Glycerol Phenylbutyrate. ChemistrySelect, 9(4), e202304021.
2365-6549
url http://hdl.handle.net/11086/552607
https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/slct.202304021
https://chemistry-europe.onlinelibrary.wiley.com/action/downloadSupplement?doi=10.1002%2Fslct.202304021&file=slct202304021-sup-0001-misc_information.pdf
https://doi.org/10.1002/slct.202304021
dc.language.none.fl_str_mv eng
language eng
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:Repositorio Digital Universitario (UNC)
instname:Universidad Nacional de Córdoba
instacron:UNC
reponame_str Repositorio Digital Universitario (UNC)
collection Repositorio Digital Universitario (UNC)
instname_str Universidad Nacional de Córdoba
instacron_str UNC
institution UNC
repository.name.fl_str_mv Repositorio Digital Universitario (UNC) - Universidad Nacional de Córdoba
repository.mail.fl_str_mv oca.unc@gmail.com
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