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Total synthesis of [(15)N]-labelled C6-substituted purines from [(15)N]-formamide—easy preparation of isotopically labelled cytokinins and derivatives
Cytokinins (CKs) and their metabolites and derivatives are essential for cell division, plant growth regulation and development. They are typically found at minute concentrations in plant tissues containing very complicated biological matrices. Therefore, defined standards labelled with stable isoto...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6281904/ https://www.ncbi.nlm.nih.gov/pubmed/30564417 http://dx.doi.org/10.1098/rsos.181322 |
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author | Buček, Jan Zatloukal, Marek Havlíček, Libor Plíhalová, Lucie Pospíšil, Tomáš Novák, Ondřej Doležal, Karel Strnad, Miroslav |
author_facet | Buček, Jan Zatloukal, Marek Havlíček, Libor Plíhalová, Lucie Pospíšil, Tomáš Novák, Ondřej Doležal, Karel Strnad, Miroslav |
author_sort | Buček, Jan |
collection | PubMed |
description | Cytokinins (CKs) and their metabolites and derivatives are essential for cell division, plant growth regulation and development. They are typically found at minute concentrations in plant tissues containing very complicated biological matrices. Therefore, defined standards labelled with stable isotopes are required for precise metabolic profiling and quantification of CKs, as well as in vivo elucidation of CK biosynthesis in various plant species. In this work, 11 [(15)N]-labelled C6-purine derivatives were prepared, among them 5 aromatic (4, 5, 6, 7, 8) and 3 isoprenoid (9, 10, 11) CKs. Compared to current methods, optimized syntheses of 6-amino-9H-[(15)N(5)]-purine (adenine) and 6-chloro-9H-[(15)N(4)]-purine (6-chloropurine) were performed to achieve more effective, selective and generally easier approaches. The chemical identity and purity of prepared compounds were confirmed by physico-chemical analyses (TLC; HRMS; HPLC–MS; (1)H, (13)C, (15)N NMR). The presented approach is applicable for the synthesis of any other desired [(15)N(4)]-labelled C6-substituted purine derivatives. |
format | Online Article Text |
id | pubmed-6281904 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | The Royal Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-62819042018-12-18 Total synthesis of [(15)N]-labelled C6-substituted purines from [(15)N]-formamide—easy preparation of isotopically labelled cytokinins and derivatives Buček, Jan Zatloukal, Marek Havlíček, Libor Plíhalová, Lucie Pospíšil, Tomáš Novák, Ondřej Doležal, Karel Strnad, Miroslav R Soc Open Sci Chemistry Cytokinins (CKs) and their metabolites and derivatives are essential for cell division, plant growth regulation and development. They are typically found at minute concentrations in plant tissues containing very complicated biological matrices. Therefore, defined standards labelled with stable isotopes are required for precise metabolic profiling and quantification of CKs, as well as in vivo elucidation of CK biosynthesis in various plant species. In this work, 11 [(15)N]-labelled C6-purine derivatives were prepared, among them 5 aromatic (4, 5, 6, 7, 8) and 3 isoprenoid (9, 10, 11) CKs. Compared to current methods, optimized syntheses of 6-amino-9H-[(15)N(5)]-purine (adenine) and 6-chloro-9H-[(15)N(4)]-purine (6-chloropurine) were performed to achieve more effective, selective and generally easier approaches. The chemical identity and purity of prepared compounds were confirmed by physico-chemical analyses (TLC; HRMS; HPLC–MS; (1)H, (13)C, (15)N NMR). The presented approach is applicable for the synthesis of any other desired [(15)N(4)]-labelled C6-substituted purine derivatives. The Royal Society 2018-11-14 /pmc/articles/PMC6281904/ /pubmed/30564417 http://dx.doi.org/10.1098/rsos.181322 Text en © 2018 The Authors. http://creativecommons.org/licenses/by/4.0/ Published by the Royal Society under the terms of the Creative Commons Attribution License http://creativecommons.org/licenses/by/4.0/, which permits unrestricted use, provided the original author and source are credited. |
spellingShingle | Chemistry Buček, Jan Zatloukal, Marek Havlíček, Libor Plíhalová, Lucie Pospíšil, Tomáš Novák, Ondřej Doležal, Karel Strnad, Miroslav Total synthesis of [(15)N]-labelled C6-substituted purines from [(15)N]-formamide—easy preparation of isotopically labelled cytokinins and derivatives |
title | Total synthesis of [(15)N]-labelled C6-substituted purines from [(15)N]-formamide—easy preparation of isotopically labelled cytokinins and derivatives |
title_full | Total synthesis of [(15)N]-labelled C6-substituted purines from [(15)N]-formamide—easy preparation of isotopically labelled cytokinins and derivatives |
title_fullStr | Total synthesis of [(15)N]-labelled C6-substituted purines from [(15)N]-formamide—easy preparation of isotopically labelled cytokinins and derivatives |
title_full_unstemmed | Total synthesis of [(15)N]-labelled C6-substituted purines from [(15)N]-formamide—easy preparation of isotopically labelled cytokinins and derivatives |
title_short | Total synthesis of [(15)N]-labelled C6-substituted purines from [(15)N]-formamide—easy preparation of isotopically labelled cytokinins and derivatives |
title_sort | total synthesis of [(15)n]-labelled c6-substituted purines from [(15)n]-formamide—easy preparation of isotopically labelled cytokinins and derivatives |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6281904/ https://www.ncbi.nlm.nih.gov/pubmed/30564417 http://dx.doi.org/10.1098/rsos.181322 |
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