A Regioselective Synthesis of Alkyl 2-(Guanin-9-yl)acetates as PNA Building Blocks from 7-(4-Nitrobenzyl)guanine Derivatives

Ferenc, Györgyi; Forgó, Péter; Kele, Zoltán; Kovács, Lajos

doi:10.1135/cccc20050085

Cited by 3 publications

(8 citation statements)

References 56 publications

(73 reference statements)

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“…[173] Sodium sulfide is known to be used for the removal of PNB group, but in the case of imidazolium 258 hydroxyl mediated ring opening occurred instead of protecting group removal and the PNB protected FAPY 259 was obtained (Scheme 43). [174] FAPY fragments are also found in natural products, for example, agelasines 260 a-c are bioactive purine derivatives with terpene side chain found in marine sponges of genus Agelas. They are associated with antimicrobial bioactivity and cytotoxic effects in cells.…”

Section: Ring Opening Of the Imidazole Moiety In Purines 31 Ring Open...mentioning

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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Section: Ring Opening Of the Imidazole Moiety In Purines 31 Ring Open...mentioning

confidence: 99%

“…Sodium sulfide is known to be used for the removal of PNB group, but in the case of imidazolium 258 hydroxyl mediated ring opening occurred instead of protecting group removal and the PNB protected FAPY 259 was obtained (Scheme 43). [174] …”

Section: Ring Opening Of the Imidazole Moiety In 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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“…( N 2 ‐Acyl‐guanin‐9‐yl)acetic esters 1 (9IbuMe), 3 (9IbutBu)4 and 5 (9PnttBu)14 have been synthesized in our laboratory as PNA monomer building blocks and studied by electrospray ionization tandem mass spectrometry (ESI‐MS/MS) along with their N 7 ‐regioisomer pairs 2 (7IbuMe) and 4 (7IbutBu), respectively4 (Fig. 1).…”

Section: Structures Of Alkylated Guanine Derivatives Studied By Ms/msmentioning

confidence: 99%

Promotion of Platinum‐Ruthenium Catalyst for Electrooxidation of Methanol by Crystalline Ruthenium Dioxide

et al. 2007

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The fuel cell is currently being established as a future 'green' energy source. The direct methanol fuel cell (DMFC) uses aqueous methanol solution as a fuel and has potential application in mobile electronics.[1] However, the high electrocatalyst cost and poor anode performance are two key handicaps which restrain the commercialization of DMFC. [2,3] The fabrication of low-loaded but active Pt catalysts for the anode is essential for the DMFC development. Practical approaches include 1) a decrease in the particle size (or high density of active sites) of Pt electrocatalysts, [4][5][6] 2) an increase in the accessibility of active sites for methanol, [7][8][9] and 3) a high resistance against CO poison.[10]CO is an intermediate in the oxidation of methanol [Eq. (1)] and poisons active Pt sites at the anode of DMFC:Adsorbed CO can be oxidized to poisonless CO 2 by water [Eq. (2)] at a cost of overpotential (h):The h required depends on the electrocatalysts used. [11,12] For monometallic Pt/C catalysts, a high h % 0.6 V is generally needed. Advanced electrocatalyst design relies on "bifunctional catalysts" [13][14][15] in which other metals are added to promote Equation (2). Ruthenium has been extensively explored as the best promoter. [1][2][3] A decrease of h to % 0.2 V was generally found for Pt-Ru/C bimetallic catalysts.Recently, Steigerwalt and co-workers [16] prepared a Pt-Ru/ GCNF nanocomposite (oxidized at 623 K) as the anode catalyst in a DMFC, and found a 50 % increase in the cell performance from an unsupported Pt-Ru catalyst. The enhanced performance was attributed to the existence of oxidized Ru species in the Pt-Ru/GCNF catalyst. In a previous report, [17] electroactivity of methanol oxidation with PtRu/C catalyst was also found promoted by oxidation treatments. The extent of promotion, however, depends on the temperature (T o ) of oxidation treatment. The promotion increased initially with T o value and optimized at T o = 520 K when the crystalline RuO 2 (c-RuO 2 ) phase began (seen through XRD) on the studied Pt-Ru/C catalyst. Herein, we report our experience on the reversibility between RuO 2 and Ru, during repetitive redox treatments of reduction (by hydrogen at T r = 620 K) and oxidation (by air at T o = 520 K) on a Pt-Ru/C bimetallic catalyst, and on the stability of c-RuO 2 during electrooxidation of methanol. A supported bimetallic catalyst of 11.1 wt % Pt-Ru/C (with a Pt/Ru atomic ratio of 1.0) was prepared by the method of incipient wetness impregnation.[10] The freshly impregnated catalyst was subsequently treated by the repetitive redox treatment. The treated catalysts were coded as Red m or Ox m , in which symbols Red and Ox denote the type (reduction or oxidation) of final treatment while the subscript m represents the number of repetitive treatments. For example, Red 1 presents an electrocatalyst from reduction of the freshly impregnated catalyst while Ox 2 catalyst is obtained from oxidation of catalyst Red 2 .

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“… The statistical analysis of 13 C NMR chemical shift parameters of over 50 compounds [3,16] revealed that guanine's δ C−5 is the most sensitive to the N 9 / N 7 substitution pattern (for the compounds studied δ C−5 (N‐9): 113.75–123.70 ppm; δ C−5 (N‐7): 104.56–115.09 ppm). However, due to the overlapping of chemical shift ranges for regioisomers (especially for glycosides) this chemical shift alone might not be sufficient for unambiguous assignment.…”

Section: Peptide Nucleic Acidsmentioning

confidence: 99%

“…En route to PNA oligomers, the difficulties accompanying the regioselective alkylation of guanine derivatives prompted us to continue our efforts towards elaborating a synthetic method to solve this vexing problem [16] …”

Section: Peptide Nucleic Acidsmentioning

confidence: 99%

From Peptide Nucleic Acids to Supramolecular Structures of Nucleic Acid Derivatives

Kovács

2022

The Chemical Record

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A Regioselective Synthesis of Alkyl 2-(Guanin-9-yl)acetates as PNA Building Blocks from 7-(4-Nitrobenzyl)guanine Derivatives

Cited by 3 publications

References 56 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

Promotion of Platinum‐Ruthenium Catalyst for Electrooxidation of Methanol by Crystalline Ruthenium Dioxide

From Peptide Nucleic Acids to Supramolecular Structures of Nucleic Acid Derivatives

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