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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2021
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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. |
format | Online Article Text |
id | pubmed-8456932 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
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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