Total synthesis of [N-15]-labelled C6-substituted purines from [N-15]-formamide-easy preparation of isotopically labelled cytokinins and derivatives

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61989592%3A15310%2F18%3A73591174" target="_blank" >RIV/61989592:15310/18:73591174 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/61389030:_____/18:00498271

Výsledek na webu

<a href="https://royalsocietypublishing.org/doi/full/10.1098/rsos.181322" target="_blank" >https://royalsocietypublishing.org/doi/full/10.1098/rsos.181322</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1098/rsos.181322." target="_blank" >10.1098/rsos.181322.</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Total synthesis of [N-15]-labelled C6-substituted purines from [N-15]-formamide-easy preparation of isotopically labelled cytokinins and derivatives

Popis výsledku v původním jazyce

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 [N-15]-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-[N-15(5)]-purine (adenine) and 6-chloro-9H-[N-15(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; H-1, C-13, N-15 NMR). The presented approach is applicable for the synthesis of any other desired [N-15(4) ]-labelled C6-substituted purine derivatives.

Název v anglickém jazyce

Total synthesis of [N-15]-labelled C6-substituted purines from [N-15]-formamide-easy preparation of isotopically labelled cytokinins and derivatives

Popis výsledku anglicky

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 [N-15]-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-[N-15(5)]-purine (adenine) and 6-chloro-9H-[N-15(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; H-1, C-13, N-15 NMR). The presented approach is applicable for the synthesis of any other desired [N-15(4) ]-labelled C6-substituted purine derivatives.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2018

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Royal Society Open Science

ISSN

2054-5703

e-ISSN

—

Svazek periodika

5

Číslo periodika v rámci svazku

11

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

14

Strana od-do

"181322-1"-"181322-14"

Kód UT WoS článku

000451777500038

EID výsledku v databázi Scopus

2-s2.0-85058399839