Chemoselective Attachment of the Water-Soluble Dark Quencher Hydrodabcyl to Amino Groups in Peptides and Preservation of Its Spectroscopic Properties over a Wide pH Range

[Image: see text] The water-soluble quencher hydrodabcyl can be activated as an N-succinimidyl ester that is readily accessible from crude hydrodabcyl and storable for a long time. With primary and secondary amines, it reacts swiftly and chemoselectively, even in the presence of other competing nucl...

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Autores principales: Kempf, Oxana, Ullmann, G. Matthias, Schobert, Rainer, Kempf, Karl, Bombarda, Elisa
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8655893/
https://www.ncbi.nlm.nih.gov/pubmed/34901640
http://dx.doi.org/10.1021/acsomega.1c04891
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author Kempf, Oxana
Ullmann, G. Matthias
Schobert, Rainer
Kempf, Karl
Bombarda, Elisa
author_facet Kempf, Oxana
Ullmann, G. Matthias
Schobert, Rainer
Kempf, Karl
Bombarda, Elisa
author_sort Kempf, Oxana
collection PubMed
description [Image: see text] The water-soluble quencher hydrodabcyl can be activated as an N-succinimidyl ester that is readily accessible from crude hydrodabcyl and storable for a long time. With primary and secondary amines, it reacts swiftly and chemoselectively, even in the presence of other competing nucleophiles such as those typically present in natural peptides. One of the three phenolic OH groups of hydrodabcyl is amenable to selective mono-Boc protection resulting in reduced polarity, advantageous to its further use in organic synthesis. The advantages of hydrodabcyl over dabcyl in spectrometric applications are exemplified by the pH dependence of its absorbance spectra.
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spelling pubmed-86558932021-12-10 Chemoselective Attachment of the Water-Soluble Dark Quencher Hydrodabcyl to Amino Groups in Peptides and Preservation of Its Spectroscopic Properties over a Wide pH Range Kempf, Oxana Ullmann, G. Matthias Schobert, Rainer Kempf, Karl Bombarda, Elisa ACS Omega [Image: see text] The water-soluble quencher hydrodabcyl can be activated as an N-succinimidyl ester that is readily accessible from crude hydrodabcyl and storable for a long time. With primary and secondary amines, it reacts swiftly and chemoselectively, even in the presence of other competing nucleophiles such as those typically present in natural peptides. One of the three phenolic OH groups of hydrodabcyl is amenable to selective mono-Boc protection resulting in reduced polarity, advantageous to its further use in organic synthesis. The advantages of hydrodabcyl over dabcyl in spectrometric applications are exemplified by the pH dependence of its absorbance spectra. American Chemical Society 2021-11-22 /pmc/articles/PMC8655893/ /pubmed/34901640 http://dx.doi.org/10.1021/acsomega.1c04891 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Kempf, Oxana
Ullmann, G. Matthias
Schobert, Rainer
Kempf, Karl
Bombarda, Elisa
Chemoselective Attachment of the Water-Soluble Dark Quencher Hydrodabcyl to Amino Groups in Peptides and Preservation of Its Spectroscopic Properties over a Wide pH Range
title Chemoselective Attachment of the Water-Soluble Dark Quencher Hydrodabcyl to Amino Groups in Peptides and Preservation of Its Spectroscopic Properties over a Wide pH Range
title_full Chemoselective Attachment of the Water-Soluble Dark Quencher Hydrodabcyl to Amino Groups in Peptides and Preservation of Its Spectroscopic Properties over a Wide pH Range
title_fullStr Chemoselective Attachment of the Water-Soluble Dark Quencher Hydrodabcyl to Amino Groups in Peptides and Preservation of Its Spectroscopic Properties over a Wide pH Range
title_full_unstemmed Chemoselective Attachment of the Water-Soluble Dark Quencher Hydrodabcyl to Amino Groups in Peptides and Preservation of Its Spectroscopic Properties over a Wide pH Range
title_short Chemoselective Attachment of the Water-Soluble Dark Quencher Hydrodabcyl to Amino Groups in Peptides and Preservation of Its Spectroscopic Properties over a Wide pH Range
title_sort chemoselective attachment of the water-soluble dark quencher hydrodabcyl to amino groups in peptides and preservation of its spectroscopic properties over a wide ph range
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8655893/
https://www.ncbi.nlm.nih.gov/pubmed/34901640
http://dx.doi.org/10.1021/acsomega.1c04891
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