Cysteine Pseudoprolines for Thiol Protection and Peptide Macrocyclization Enhancement in Fmoc-Based Solid-Phase Peptide Synthesis

[Image: see text] Contrary to other studies, here we describe cysteine (Cys) pseudoproline-containing peptides with short deprotection times in TFA. The deprotection times fell in the same range as other protecting groups commonly used in SPPS (e.g., 1–3 h). Moreover, when using Cys pseudoprolines a...

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Autores principales: Postma, Tobias M., Albericio, Fernando
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3971734/
https://www.ncbi.nlm.nih.gov/pubmed/24617568
http://dx.doi.org/10.1021/ol5004725
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author Postma, Tobias M.
Albericio, Fernando
author_facet Postma, Tobias M.
Albericio, Fernando
author_sort Postma, Tobias M.
collection PubMed
description [Image: see text] Contrary to other studies, here we describe cysteine (Cys) pseudoproline-containing peptides with short deprotection times in TFA. The deprotection times fell in the same range as other protecting groups commonly used in SPPS (e.g., 1–3 h). Moreover, when using Cys pseudoprolines as peptide macrocyclization-enhancing moieties a considerable reduction in reaction time was observed compared to a peptide containing trityl protected Cys.
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spelling pubmed-39717342014-04-01 Cysteine Pseudoprolines for Thiol Protection and Peptide Macrocyclization Enhancement in Fmoc-Based Solid-Phase Peptide Synthesis Postma, Tobias M. Albericio, Fernando Org Lett [Image: see text] Contrary to other studies, here we describe cysteine (Cys) pseudoproline-containing peptides with short deprotection times in TFA. The deprotection times fell in the same range as other protecting groups commonly used in SPPS (e.g., 1–3 h). Moreover, when using Cys pseudoprolines as peptide macrocyclization-enhancing moieties a considerable reduction in reaction time was observed compared to a peptide containing trityl protected Cys. American Chemical Society 2014-03-11 2014-03-21 /pmc/articles/PMC3971734/ /pubmed/24617568 http://dx.doi.org/10.1021/ol5004725 Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Postma, Tobias M.
Albericio, Fernando
Cysteine Pseudoprolines for Thiol Protection and Peptide Macrocyclization Enhancement in Fmoc-Based Solid-Phase Peptide Synthesis
title Cysteine Pseudoprolines for Thiol Protection and Peptide Macrocyclization Enhancement in Fmoc-Based Solid-Phase Peptide Synthesis
title_full Cysteine Pseudoprolines for Thiol Protection and Peptide Macrocyclization Enhancement in Fmoc-Based Solid-Phase Peptide Synthesis
title_fullStr Cysteine Pseudoprolines for Thiol Protection and Peptide Macrocyclization Enhancement in Fmoc-Based Solid-Phase Peptide Synthesis
title_full_unstemmed Cysteine Pseudoprolines for Thiol Protection and Peptide Macrocyclization Enhancement in Fmoc-Based Solid-Phase Peptide Synthesis
title_short Cysteine Pseudoprolines for Thiol Protection and Peptide Macrocyclization Enhancement in Fmoc-Based Solid-Phase Peptide Synthesis
title_sort cysteine pseudoprolines for thiol protection and peptide macrocyclization enhancement in fmoc-based solid-phase peptide synthesis
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3971734/
https://www.ncbi.nlm.nih.gov/pubmed/24617568
http://dx.doi.org/10.1021/ol5004725
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