Synthesis of 4,6-Difluoro-Tryptophan as a Probe for Protein 19F NMR

A scalable procedure for the synthesis of 4,6-difluorotryptophan is reported based on a deaminative coupling of a 4,6-difluorogramine with 2-benzylthio-1,5-dihydro-4H-imidazolone as glycine equivalent. Thus prepared 4,6-difluorotryptophan was incorporated into the C-terminal domain of the HIV-1 caps...

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Autores: Monnie, Christina M., Hernández Morales, Iker, Meléndez Pacheco, Raixie, Bhinderwala, Fatema, Soloshonok, Vadym Anatolievch, Gronenborn, Angela M., Landa Álvarez, Aitor, Oyarbide Garmendia, Juan Miguel
Tipo de recurso: artículo
Fecha de publicación:2024
País:España
Institución:Universidad del País Vasco
Repositorio:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/68415
Acceso en línea:http://hdl.handle.net/10810/68415
Access Level:acceso abierto
Palabra clave:fluorinated tryptophans
amino acid synthesis
gramines coupling
protein 19F NMR
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spelling Synthesis of 4,6-Difluoro-Tryptophan as a Probe for Protein 19F NMRMonnie, Christina M.Hernández Morales, IkerMeléndez Pacheco, RaixieBhinderwala, FatemaSoloshonok, Vadym AnatolievchGronenborn, Angela M.Landa Álvarez, AitorOyarbide Garmendia, Juan Miguelfluorinated tryptophansamino acid synthesisgramines couplingprotein 19F NMRA scalable procedure for the synthesis of 4,6-difluorotryptophan is reported based on a deaminative coupling of a 4,6-difluorogramine with 2-benzylthio-1,5-dihydro-4H-imidazolone as glycine equivalent. Thus prepared 4,6-difluorotryptophan was incorporated into the C-terminal domain of the HIV-1 capsid protein (CA-CTD), and 19F spectra of the 4,6-difluoro Trp CA CTD were recorded and compared to the singly fluorinated counterparts.We thank the Basque Government (EJ, grant IT1583-22) and Agencia Estatal de Investigación (grants PID2019-109633GB-C21/AEI/10.13039/501100011033 and PID2022-137153NB-C21/AEI/10.13039/501100011033) for financial support. The authors are grateful for the technical and human support provided by SGIker (UPV/EHU/ERDF, EU). I.H. thanks EJ for a fellowship. R.M-P. was supported by the Health Sciences Diversity Scholars Program at the University of Pittsburgh and F.B. by a post-doctoral fellowship from the American Heart Association. The work in the Gronenborn laboratory was supported by NIH grant U54AI170791.Wiley-VCH GmbH, Weinheim202420242024info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10810/68415reponame:Addi. Archivo Digital para la Docencia y la Investigacióninstname:Universidad del País VascoIngléshttps://onlinelibrary.wiley.com/doi/full/10.1002/adsc.202400031info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/4.0/© 2024 The Authors. Advanced Synthesis & Catalysis published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License.oai:addi.ehu.eus:10810/684152026-06-18T09:23:17Z
dc.title.none.fl_str_mv Synthesis of 4,6-Difluoro-Tryptophan as a Probe for Protein 19F NMR
title Synthesis of 4,6-Difluoro-Tryptophan as a Probe for Protein 19F NMR
spellingShingle Synthesis of 4,6-Difluoro-Tryptophan as a Probe for Protein 19F NMR
Monnie, Christina M.
fluorinated tryptophans
amino acid synthesis
gramines coupling
protein 19F NMR
title_short Synthesis of 4,6-Difluoro-Tryptophan as a Probe for Protein 19F NMR
title_full Synthesis of 4,6-Difluoro-Tryptophan as a Probe for Protein 19F NMR
title_fullStr Synthesis of 4,6-Difluoro-Tryptophan as a Probe for Protein 19F NMR
title_full_unstemmed Synthesis of 4,6-Difluoro-Tryptophan as a Probe for Protein 19F NMR
title_sort Synthesis of 4,6-Difluoro-Tryptophan as a Probe for Protein 19F NMR
dc.creator.none.fl_str_mv Monnie, Christina M.
Hernández Morales, Iker
Meléndez Pacheco, Raixie
Bhinderwala, Fatema
Soloshonok, Vadym Anatolievch
Gronenborn, Angela M.
Landa Álvarez, Aitor
Oyarbide Garmendia, Juan Miguel
author Monnie, Christina M.
author_facet Monnie, Christina M.
Hernández Morales, Iker
Meléndez Pacheco, Raixie
Bhinderwala, Fatema
Soloshonok, Vadym Anatolievch
Gronenborn, Angela M.
Landa Álvarez, Aitor
Oyarbide Garmendia, Juan Miguel
author_role author
author2 Hernández Morales, Iker
Meléndez Pacheco, Raixie
Bhinderwala, Fatema
Soloshonok, Vadym Anatolievch
Gronenborn, Angela M.
Landa Álvarez, Aitor
Oyarbide Garmendia, Juan Miguel
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv fluorinated tryptophans
amino acid synthesis
gramines coupling
protein 19F NMR
topic fluorinated tryptophans
amino acid synthesis
gramines coupling
protein 19F NMR
description A scalable procedure for the synthesis of 4,6-difluorotryptophan is reported based on a deaminative coupling of a 4,6-difluorogramine with 2-benzylthio-1,5-dihydro-4H-imidazolone as glycine equivalent. Thus prepared 4,6-difluorotryptophan was incorporated into the C-terminal domain of the HIV-1 capsid protein (CA-CTD), and 19F spectra of the 4,6-difluoro Trp CA CTD were recorded and compared to the singly fluorinated counterparts.
publishDate 2024
dc.date.none.fl_str_mv 2024
2024
2024
dc.type.none.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10810/68415
url http://hdl.handle.net/10810/68415
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv https://onlinelibrary.wiley.com/doi/full/10.1002/adsc.202400031
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/4.0/
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/4.0/
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley-VCH GmbH, Weinheim
publisher.none.fl_str_mv Wiley-VCH GmbH, Weinheim
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 15,811543

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