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Search for "purine nucleosides" in Full Text gives 12 result(s) in Beilstein Journal of Organic Chemistry.
Synthetic strategies toward 1,3-oxathiolane nucleoside analogues
Beilstein J. Org. Chem. 2021, 17, 2680–2715, doi:10.3762/bjoc.17.182
- of TMSOTf for the N-glycosylation procedure afforded a racemic mixture. This could be due to the opening as well as closing of the oxathiolane ring under the reaction conditions. Optically pure β-ᴅ- and α-ᴅ-configured 1,3-oxathiolane pyrimidine and 1,3-oxathiolane purine nucleosides with natural
1,2,3-Triazoles as leaving groups: SNAr reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles
Beilstein J. Org. Chem. 2021, 17, 410–419, doi:10.3762/bjoc.17.37
- ring at the C6 position of purine to act as leaving group. Keywords: 2,6-bistriazolyl purines; nucleophilic aromatic substitution; purine nucleosides; triazoles; Introduction Modified purine derivatives are an important class of compounds which possess a wide spectrum of biological activities [1][2
Changed reactivity of secondary hydroxy groups in C8-modified adenosine – lessons learned from silylation
Beilstein J. Org. Chem. 2020, 16, 2854–2861, doi:10.3762/bjoc.16.234
- building blocks of the purine nucleosides with functionalities suitable for post-synthetic conjugation at the nucleobase are basically missing, and also in the pyrimidine series, the few existing derivatives of uridine do not offer much variety. Motivated by this lack of functional building blocks, we have
Anion exchange resins in phosphate form as versatile carriers for the reactions catalyzed by nucleoside phosphorylases
Beilstein J. Org. Chem. 2020, 16, 2607–2622, doi:10.3762/bjoc.16.212
- enzymatic syntheses of biologically important purine nucleosides, on the other hand (Scheme 1). As might be expected, the replacement of phosphate buffer with Dowex-nPi in the phosphorolysis of uridine (Urd), thymidine (Thd), and 1-(β-ᴅ-arabinofuranosyl)uracil (Ara-U) slowed down the reaction rate and
- discussed above prompted us to start the search for simple and at the same time effective methods for the enzymatic synthesis of α-ᴅ-pentofuanose-1-phosphates (PF-1Pis) as key intermediates for the synthesis of nucleosides according to Kalсkar by phosphorolysis of readily available pyrimidine and purine
- nucleosides. With this aim in view, studies have initiated on the synthesis of Rib-1Pi, dRib-1Pi, and Ara-1Pi based on the corresponding pyrimidine nucleosides and E. coli UP and TP in the presence of Dowex® 1X8 in phosphate form (100–200 mesh; Dowex-nPi) as a source of inorganic phosphate in water instead of
Recent developments in photoredox-catalyzed remote ortho and para C–H bond functionalizations
Beilstein J. Org. Chem. 2020, 16, 248–280, doi:10.3762/bjoc.16.26
- previously reported methods required high temperatures [118][119][120]. A library of compounds was reported by that group using this approach, and a plausible mechanism is shown in Figure 13. Arylation of purines: Purine bases and purine nucleosides, which are common structural motifs in DNA and RNA, have an
Synthetic mRNA capping
Beilstein J. Org. Chem. 2017, 13, 2819–2832, doi:10.3762/bjoc.13.274
- hydrolytically less stable than other purine nucleosides. Under basic conditions which are commonly used for RNA deprotection and cleavage from the solid support, opening of the imidazole ring of the 7-methylguanine would occur [111]. Thus, for synthesis of the cap structure on the solid support, standard
Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill
Beilstein J. Org. Chem. 2017, 13, 87–92, doi:10.3762/bjoc.13.11
- ′-tosylates in five to 60 minutes. Under these conditions, commonly-encountered nucleoside cyclisation byproducts (especially of purine nucleosides) were not observed. Liquid-assisted grinding of the same 5'-iodide and 5′-tosylate substrates with potassium selenocyanate in the presence of DMF produced the
The role of alkyl substituents in deazaadenine-based diarylethene photoswitches
Beilstein J. Org. Chem. 2016, 12, 1103–1110, doi:10.3762/bjoc.12.106
- diarylethenes by direct comparison, and ii) we wanted to test whether our prior successful violation of this “rule” with photochromic pyrimidine nucleosides could be expanded to purine nucleosides. Our analysis reveals that – depending on the substituents – the one-methyl 7-deaza-2’-deoxyadenosine compounds can
Versatile synthesis and biological evaluation of novel 3’-fluorinated purine nucleosides
Beilstein J. Org. Chem. 2015, 11, 2509–2520, doi:10.3762/bjoc.11.272
- ’-fluororibofuranose intermediate. Employing Suzuki and Stille cross-coupling reactions, fifteen 3’-fluororibose purine nucleosides 1–15 and eight 3’-fluororibose 2-chloro/2-aminopurine nucleosides 16–23 with various substituents at position 6 of the purine ring were efficiently synthesized. Furthermore, 3’-fluorine
- -lines [14][15][16]. Moreover, some 6-heterocyclic substituted purine ribonucleosides also demonstrate strong antiviral activities [17]. Purine derivatives such as, 2’-β-C-methyl-6-substituted purine nucleosides exhibit promising anti-HCV activity by blocking RNA dependent RNA polymerase [18][19][20
- potent novel antiviral and anticancer therapeutics. Various fluorine-modified ribonucleoside derivatives were designed, synthesized, and tested. The preliminary results are presented herein. We utilized the structural characteristics of 3’-fluorine and 6-substituted purine nucleosides to expand their
Versatile synthesis of amino acid functionalized nucleosides via a domino carboxamidation reaction
Beilstein J. Org. Chem. 2014, 10, 2566–2572, doi:10.3762/bjoc.10.268
- lysine derivatives onto nucleosides via a straightforward and easy domino carboxamidation reaction. Previously the groups of Gait and Eaton [41][42][43] have used this reaction to couple histamine or simple amine derivatives to both 5-iodo-2’-deoxyuridine and purine nucleosides. Although a large number
Facile synthesis of 1-alkoxy-1H-benzo- and 7-azabenzotriazoles from peptide coupling agents, mechanistic studies, and synthetic applications
Beilstein J. Org. Chem. 2014, 10, 1919–1932, doi:10.3762/bjoc.10.200
- appeared implausible on the basis of prior observations, where no reaction of BOP with the free hydroxy groups of nucleosides was observed [23][25]. Our recent work on a two-step one-pot etherification of purine nucleosides, quinazoline, and pyrimidines, had led some interesting preliminary observations
The chemoenzymatic synthesis of clofarabine and related 2′-deoxyfluoroarabinosyl nucleosides: the electronic and stereochemical factors determining substrate recognition by E. coli nucleoside phosphorylases
Beilstein J. Org. Chem. 2014, 10, 1657–1669, doi:10.3762/bjoc.10.173
- [35]: (MeOH) λmax, nm (ε, M−1cm−1) 258 (14,600). The 1H and 13C NMR spectra of the synthesized nucleoside 4a are similar to those previously described for the authentic sample [35]. The structures of purine nucleosides studied in the chemoenzymatic synthesis and in a cascade one-pot transformation of
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