Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Buček, Jan, Zatloukal, Marek, Havlíček, Libor, Plíhalová, Lucie, Pospíšil, Tomáš, Novák, Ondřej, Doležal, Karel, Strnad, Miroslav
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society 2018
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
_version_ 1783378885498372096
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
work_keys_str_mv AT bucekjan totalsynthesisof15nlabelledc6substitutedpurinesfrom15nformamideeasypreparationofisotopicallylabelledcytokininsandderivatives
AT zatloukalmarek totalsynthesisof15nlabelledc6substitutedpurinesfrom15nformamideeasypreparationofisotopicallylabelledcytokininsandderivatives
AT havliceklibor totalsynthesisof15nlabelledc6substitutedpurinesfrom15nformamideeasypreparationofisotopicallylabelledcytokininsandderivatives
AT plihalovalucie totalsynthesisof15nlabelledc6substitutedpurinesfrom15nformamideeasypreparationofisotopicallylabelledcytokininsandderivatives
AT pospisiltomas totalsynthesisof15nlabelledc6substitutedpurinesfrom15nformamideeasypreparationofisotopicallylabelledcytokininsandderivatives
AT novakondrej totalsynthesisof15nlabelledc6substitutedpurinesfrom15nformamideeasypreparationofisotopicallylabelledcytokininsandderivatives
AT dolezalkarel totalsynthesisof15nlabelledc6substitutedpurinesfrom15nformamideeasypreparationofisotopicallylabelledcytokininsandderivatives
AT strnadmiroslav totalsynthesisof15nlabelledc6substitutedpurinesfrom15nformamideeasypreparationofisotopicallylabelledcytokininsandderivatives