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Amphiphilic Iodine(III) Reagents for the Lipophilization of Peptides in Water

We report the functionalization of cysteine residues with lipophilic alkynes bearing a silyl group or an alkyl chain using amphiphilic ethynylbenziodoxolone reagents (EBXs). The reactions were carried out in buffer (pH 6 to 9), without organic co‐solvent or removal of oxygen, either at 37 °C or room...

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Autores principales: Mishra, Abhaya Kumar, Tessier, Romain, Hari, Durga Prasad, Waser, Jerome
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8456932/
https://www.ncbi.nlm.nih.gov/pubmed/34038604
http://dx.doi.org/10.1002/anie.202106458
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author Mishra, Abhaya Kumar
Tessier, Romain
Hari, Durga Prasad
Waser, Jerome
author_facet Mishra, Abhaya Kumar
Tessier, Romain
Hari, Durga Prasad
Waser, Jerome
author_sort Mishra, Abhaya Kumar
collection PubMed
description We report the functionalization of cysteine residues with lipophilic alkynes bearing a silyl group or an alkyl chain using amphiphilic ethynylbenziodoxolone reagents (EBXs). The reactions were carried out in buffer (pH 6 to 9), without organic co‐solvent or removal of oxygen, either at 37 °C or room temperature. The transformation led to a significant increase of peptide lipophilicity and worked for aromatic thiols, homocysteine, cysteine, and peptides containing 4 to 18 amino acids. His(6)‐Cys‐Ubiquitin was also alkynylated under physiological conditions. Under acidic conditions, the thioalkynes were converted into thioesters, which could be cleaved in the presence of hydroxylamine.
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spelling pubmed-84569322021-09-27 Amphiphilic Iodine(III) Reagents for the Lipophilization of Peptides in Water Mishra, Abhaya Kumar Tessier, Romain Hari, Durga Prasad Waser, Jerome Angew Chem Int Ed Engl Communications We report the functionalization of cysteine residues with lipophilic alkynes bearing a silyl group or an alkyl chain using amphiphilic ethynylbenziodoxolone reagents (EBXs). The reactions were carried out in buffer (pH 6 to 9), without organic co‐solvent or removal of oxygen, either at 37 °C or room temperature. The transformation led to a significant increase of peptide lipophilicity and worked for aromatic thiols, homocysteine, cysteine, and peptides containing 4 to 18 amino acids. His(6)‐Cys‐Ubiquitin was also alkynylated under physiological conditions. Under acidic conditions, the thioalkynes were converted into thioesters, which could be cleaved in the presence of hydroxylamine. John Wiley and Sons Inc. 2021-07-12 2021-08-09 /pmc/articles/PMC8456932/ /pubmed/34038604 http://dx.doi.org/10.1002/anie.202106458 Text en © 2021 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Mishra, Abhaya Kumar
Tessier, Romain
Hari, Durga Prasad
Waser, Jerome
Amphiphilic Iodine(III) Reagents for the Lipophilization of Peptides in Water
title Amphiphilic Iodine(III) Reagents for the Lipophilization of Peptides in Water
title_full Amphiphilic Iodine(III) Reagents for the Lipophilization of Peptides in Water
title_fullStr Amphiphilic Iodine(III) Reagents for the Lipophilization of Peptides in Water
title_full_unstemmed Amphiphilic Iodine(III) Reagents for the Lipophilization of Peptides in Water
title_short Amphiphilic Iodine(III) Reagents for the Lipophilization of Peptides in Water
title_sort amphiphilic iodine(iii) reagents for the lipophilization of peptides in water
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8456932/
https://www.ncbi.nlm.nih.gov/pubmed/34038604
http://dx.doi.org/10.1002/anie.202106458
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