Scope and Limitations of γ-Valerolactone (GVL) as a Green Solvent to be Used with Base for Fmoc Removal in Solid Phase Peptide Synthesis

GVL is a green solvent used in Fmoc-based solid-phase peptide synthesis. It is susceptible to ring opening in the presence of bases such as piperidines, which are used to remove the Fmoc protecting group. Here we studied the formation of the corresponding acyl piperidides by time-dependent monitorin...

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Detalles Bibliográficos
Autores principales: Kumar, Ashish, Sharma, Anamika, de la Torre, Beatriz G., Albericio, Fernando
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6864637/
https://www.ncbi.nlm.nih.gov/pubmed/31694279
http://dx.doi.org/10.3390/molecules24214004
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author Kumar, Ashish
Sharma, Anamika
de la Torre, Beatriz G.
Albericio, Fernando
author_facet Kumar, Ashish
Sharma, Anamika
de la Torre, Beatriz G.
Albericio, Fernando
author_sort Kumar, Ashish
collection PubMed
description GVL is a green solvent used in Fmoc-based solid-phase peptide synthesis. It is susceptible to ring opening in the presence of bases such as piperidines, which are used to remove the Fmoc protecting group. Here we studied the formation of the corresponding acyl piperidides by time-dependent monitoring using NMR. The results, corroborated by theoretical calculations, indicate that a solution of piperidines in GVL should be prepared daily for a better Fmoc removal.
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spelling pubmed-68646372019-12-23 Scope and Limitations of γ-Valerolactone (GVL) as a Green Solvent to be Used with Base for Fmoc Removal in Solid Phase Peptide Synthesis Kumar, Ashish Sharma, Anamika de la Torre, Beatriz G. Albericio, Fernando Molecules Article GVL is a green solvent used in Fmoc-based solid-phase peptide synthesis. It is susceptible to ring opening in the presence of bases such as piperidines, which are used to remove the Fmoc protecting group. Here we studied the formation of the corresponding acyl piperidides by time-dependent monitoring using NMR. The results, corroborated by theoretical calculations, indicate that a solution of piperidines in GVL should be prepared daily for a better Fmoc removal. MDPI 2019-11-05 /pmc/articles/PMC6864637/ /pubmed/31694279 http://dx.doi.org/10.3390/molecules24214004 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Kumar, Ashish
Sharma, Anamika
de la Torre, Beatriz G.
Albericio, Fernando
Scope and Limitations of γ-Valerolactone (GVL) as a Green Solvent to be Used with Base for Fmoc Removal in Solid Phase Peptide Synthesis
title Scope and Limitations of γ-Valerolactone (GVL) as a Green Solvent to be Used with Base for Fmoc Removal in Solid Phase Peptide Synthesis
title_full Scope and Limitations of γ-Valerolactone (GVL) as a Green Solvent to be Used with Base for Fmoc Removal in Solid Phase Peptide Synthesis
title_fullStr Scope and Limitations of γ-Valerolactone (GVL) as a Green Solvent to be Used with Base for Fmoc Removal in Solid Phase Peptide Synthesis
title_full_unstemmed Scope and Limitations of γ-Valerolactone (GVL) as a Green Solvent to be Used with Base for Fmoc Removal in Solid Phase Peptide Synthesis
title_short Scope and Limitations of γ-Valerolactone (GVL) as a Green Solvent to be Used with Base for Fmoc Removal in Solid Phase Peptide Synthesis
title_sort scope and limitations of γ-valerolactone (gvl) as a green solvent to be used with base for fmoc removal in solid phase peptide synthesis
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6864637/
https://www.ncbi.nlm.nih.gov/pubmed/31694279
http://dx.doi.org/10.3390/molecules24214004
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