Transformations of the natural cytokinin N6-isopentenyladenine in aqueous acidic media: structural aspects

Trávníček, Zdeněk; Novotná, Radka; Marek, Jaromı́r; Popa, Igor; Šipl, Michal

doi:10.1039/c1ob05649b

Cited by 6 publications

(6 citation statements)

References 35 publications

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“…Cycloisomerization to 210 and opening of the activated pyrimidine moiety yielded the ring‐opened product 211 (Scheme 32). [151] …”

Section: Ring Opening Of the Pyrimidine Moiety In Purinesmentioning

confidence: 99%

“…Cycloisomerization to 210 and opening of the activated pyrimidine moiety yielded the ring-opened product 211 (Scheme 32). [151] Guanosine deamination product -oxanine (215) formed via transnitrosation from N-nitrosoindole-3-acetonitrile 216, a plant growth hormone present in various vegetables, notably Chinese cabbage. The reaction was initiated by nitrosation of guanosine (212) that produced the diazonium salt 213.…”

Section: Ring Opening Of N-1-quaternized Purinesmentioning

confidence: 99%

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Applications of Purine Ring Opening in the Synthesis of Imidazole, Pyrimidine, and New Purine Derivatives

et al. 2021

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Purines, which are regarded as relatively stable heterocyclic systems, can be opened at both pyrimidine and imidazole rings. Purine ring opening also serves as a tool for the preparation of ring-modified purines through rearrangement/recyclization mechanisms. The obtained imidazole, pyrimidine, and purine derivatives are privileged molecular scaffolds in medicinal and agricultural chemistry. Purine ring-opening approach is a useful alternative for their synthesis, which competes well with de novo approach or modification of a conserved heterocyclic core. The substitution patterns and groups that activate purines towards ring opening are reviewed. Moreover, mechanistic studies using labelled substrates, which are leading to rearranged purine derivatives are covered. Furthermore, an insight into imidazole ring opening upon exposure of purine system to DNA damaging agents is provided.

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“…Cycloisomerization to 210 and opening of the activated pyrimidine moiety yielded the ring‐opened product 211 (Scheme 32). [151] …”

Section: Ring Opening Of the Pyrimidine Moiety In Purinesmentioning

confidence: 99%

Section: Ring Opening Of N-1-quaternized Purinesmentioning

confidence: 99%

Applications of Purine Ring Opening in the Synthesis of Imidazole, Pyrimidine, and New Purine Derivatives

et al. 2021

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“…Acid hydrolysis of cytokinin nucleosides with aromatic residues leads to CKs in high yields. At the same time, the isopentenyl side chain is rather labile under these conditions (Trávníček, Novotná, Marek, Popa, & Šipl, ). The enzymatic hydrolysis of the N ‐glycosidic bond can be a method of choice for the preparation of various CK derivatives starting from N 6 ‐substituted adenosines.…”

Section: Commentarymentioning

confidence: 99%

“…According to our TLC results, most of the reactions were complete in 3 hr, after which they were cooled and neutralized to pH 7 with 25% aqueous ammonia. However, this method is suitable only for the preparation of aromatic and non‐labile saturated CK derivatives and cannot be used for isopentenyl derivatives (Trávníček et al., ). Nucleoside phosphorylases catalyze the formation of nucleosides from the corresponding nucleobases and α‐ D ‐ribose‐1‐phosphate and are widely used for the preparation of practically important nucleosides (Figure ).…”

Section: Commentarymentioning

confidence: 99%

Synthesis of Cytokinins via Enzymatic Arsenolysis of Purine Nucleosides

Oslovsky

Drenichev

Alexeev

et al. 2018

CP Nucleic Acid Chemistry

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This unit describes an effective method for the preparation of natural cytokinins and their synthetic derivatives based on enzymatic cleavage of the N‐glycosidic bond of N6‐substituted adenosine or O6‐substituted inosine derivatives in the presence of purine nucleoside phosphorylase (PNP) and Na2HAsO4. The arsenolysis reaction is irreversible due to the hydrolysis of the resulting α‐D‐ribose‐1‐arsenate. As a result, the desired products are formed in near‐quantitative yields, as indicated by high‐performance liquid chromatography (HPLC) analysis, and can easily be isolated. In the strategy used here, the ribose residue acts as a protective group. © 2018 by John Wiley & Sons, Inc.

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“…Natural occurring CTKs are derived from adenine and carry either an aromatic or isoprene side chain on their N6 position as shown in Figure . Some CTKs like kinetin (KT), N6‐isopentenyl adenine (IP), zeatin and 6‐benzylaminopurine, have been commonly used in agricultural production in recent years. CTKs are well‐known to function as plant hormones and to interfere many physiological processes through their interactions with enzymes and proteins involved in plant growth and development process …”

Section: Introductionmentioning

confidence: 99%

Molecular Interaction Kinetics and Mechanism Study of Phytohormones and Plant Protein with Fluorescence and Synchronous Fluorescence Techniques

Zheng

Sun

et al. 2017

ChemistrySelect

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Cytokinins (CTKs) are widely used in agriculture to enhance crop production. To understand the role of CTKs in plant growth is vital, however, molecular mechanisms underlying CTKs action particularly their binding kinetics with proteins are not clear. The study of these interactions can obtain important information on how these signal molecules regulate cellular processes in targeted cells locally or transport to other functional parts of plants. In this study, the interactions between two CTKs and soy protein were investigated. The binding constants determined at 30 o C were K KT-soy = 1.5 3 10 3 M À1 and K IP-soy = 0.67 3 10 2 M À1 and the binding stoichiometry was n KT-soy = 0.530 and n IP-soy = 0.5165 respectively. Moreover, the CTK-protein interaction is found to be a static quenching process via an energy transfer mechanism. The adduct formed through electrostatic interactions under the plant acidity conditions was thus transported to the action parts of the plant to control growth process.

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Transformations of the natural cytokinin N6-isopentenyladenine in aqueous acidic media: structural aspects

Cited by 6 publications

References 35 publications

Applications of Purine Ring Opening in the Synthesis of Imidazole, Pyrimidine, and New Purine Derivatives

Applications of Purine Ring Opening in the Synthesis of Imidazole, Pyrimidine, and New Purine Derivatives

Synthesis of Cytokinins via Enzymatic Arsenolysis of Purine Nucleosides

Molecular Interaction Kinetics and Mechanism Study of Phytohormones and Plant Protein with Fluorescence and Synchronous Fluorescence Techniques

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