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Synthesis of coumarin or ferrocene labeled nucleosides via Staudinger ligation
BACKGROUND: Reaction of azides with triaryl phosphines under mild conditions gives iminophosphoranes which can react with almost any kind of electrophilic reagent, e.g. aldehydes/ketones to form imines or esters to form amides. This so-called Staudinger ligation has been employed in a wide range of...
Autores principales: | , , |
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Formato: | Texto |
Lenguaje: | English |
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Beilstein-Institut
2006
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1779791/ https://www.ncbi.nlm.nih.gov/pubmed/17137496 http://dx.doi.org/10.1186/1860-5397-2-23 |
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author | Kosiova, Ivana Janicova, Andrea Kois, Pavol |
author_facet | Kosiova, Ivana Janicova, Andrea Kois, Pavol |
author_sort | Kosiova, Ivana |
collection | PubMed |
description | BACKGROUND: Reaction of azides with triaryl phosphines under mild conditions gives iminophosphoranes which can react with almost any kind of electrophilic reagent, e.g. aldehydes/ketones to form imines or esters to form amides. This so-called Staudinger ligation has been employed in a wide range of applications as a general tool for bioconjugation including specific labeling of nucleic acids. RESULTS: A new approach for the preparation of labeled nucleosides via intermolecular Staudinger ligation is described. Reaction of azidonucleosides with triphenylphosphine lead to iminophosphorane intermediates, which react subsequently with derivatives of coumarin or ferrocene to form coumarin or ferrocene labeled nucleosides. Fluorescent properties of coumarin labeled nucleosides are determined. CONCLUSION: New coumarin and ferrocene labeled nucleosides were prepared via intermolecular Staudinger ligation. This reaction joins the fluorescent coumarin and biospecific nucleoside to the new molecule with promising fluorescent and electrochemical properties. The isolated yields of products depend on the structure of azidonucleoside and carboxylic acids. A detailed study of the kinetics of the Staudinger ligation with nucleoside substrates is in progress. |
format | Text |
id | pubmed-1779791 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2006 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-17797912007-01-20 Synthesis of coumarin or ferrocene labeled nucleosides via Staudinger ligation Kosiova, Ivana Janicova, Andrea Kois, Pavol Beilstein J Org Chem Full Research Paper BACKGROUND: Reaction of azides with triaryl phosphines under mild conditions gives iminophosphoranes which can react with almost any kind of electrophilic reagent, e.g. aldehydes/ketones to form imines or esters to form amides. This so-called Staudinger ligation has been employed in a wide range of applications as a general tool for bioconjugation including specific labeling of nucleic acids. RESULTS: A new approach for the preparation of labeled nucleosides via intermolecular Staudinger ligation is described. Reaction of azidonucleosides with triphenylphosphine lead to iminophosphorane intermediates, which react subsequently with derivatives of coumarin or ferrocene to form coumarin or ferrocene labeled nucleosides. Fluorescent properties of coumarin labeled nucleosides are determined. CONCLUSION: New coumarin and ferrocene labeled nucleosides were prepared via intermolecular Staudinger ligation. This reaction joins the fluorescent coumarin and biospecific nucleoside to the new molecule with promising fluorescent and electrochemical properties. The isolated yields of products depend on the structure of azidonucleoside and carboxylic acids. A detailed study of the kinetics of the Staudinger ligation with nucleoside substrates is in progress. Beilstein-Institut 2006-11-30 /pmc/articles/PMC1779791/ /pubmed/17137496 http://dx.doi.org/10.1186/1860-5397-2-23 Text en Copyright © 2006, Kosiova et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms) |
spellingShingle | Full Research Paper Kosiova, Ivana Janicova, Andrea Kois, Pavol Synthesis of coumarin or ferrocene labeled nucleosides via Staudinger ligation |
title | Synthesis of coumarin or ferrocene labeled nucleosides via Staudinger ligation |
title_full | Synthesis of coumarin or ferrocene labeled nucleosides via Staudinger ligation |
title_fullStr | Synthesis of coumarin or ferrocene labeled nucleosides via Staudinger ligation |
title_full_unstemmed | Synthesis of coumarin or ferrocene labeled nucleosides via Staudinger ligation |
title_short | Synthesis of coumarin or ferrocene labeled nucleosides via Staudinger ligation |
title_sort | synthesis of coumarin or ferrocene labeled nucleosides via staudinger ligation |
topic | Full Research Paper |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1779791/ https://www.ncbi.nlm.nih.gov/pubmed/17137496 http://dx.doi.org/10.1186/1860-5397-2-23 |
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