8‐Aza‐2′‐deoxyguanosine and Related 1,2,3‐Triazolo[4,5‐<i>d</i>]pyrimidine 2′‐Deoxyribofuranosides

Seela, Frank; Lampe, S.

doi:10.1002/hlca.19930760625

Cited by 25 publications

(22 citation statements)

References 15 publications

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“…[72] Ribosides and deoxyribosides of 8-azaDaPur have been synthesized many years ago, [73,74] but their fluorescence properties were not examined until recently. We have found that enzymatically generated N9-, N8-, and N7-β-d-ribosides of 8-azaDaPur are highly fluorescent, [75] with yields of ca.…”

Section: 6-diamino-8-azapurine and The Corresponding Ribosidesmentioning

confidence: 99%

Excited-State Proton Transfer and Phototautomerism in Nucleobase and Nucleoside Analogs: A Mini-Review

Wierzchowski¹

2014

Nucleosides, Nucleotides and Nucleic Acids

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Intermolecular excited-state proton transfer (ESPT) has been observed in several fluorescent nucleobase and/or nucleoside analogs. In the present work, some new examples of ESPT in this class of compounds are presented together with a brief recapitulation of the previously published data. The nucleobases, nucleosides, and their analogs contain many basic and acidic centers and therefore their ESPT behavior may be complex. To interpret the complex data, it is usually necessary to determine the microscopic pK* values for each (or most) of the possible ESPT centers. Typical approach to solve this problem is by analysis of the alkyl derivatives, in which the possibility of the ESPT is reduced. Of particular interest are examples of "phototautomerization via the cation," observed in several systems, which in the neutral media do not undergo ESPT. Protonation of the molecule in the ground state facilitates the two-step phototautomerism in several systems, including formycin A and 2-amino-8-azadenine. Fluorescence of the nucleobase and nucleoside analogs undergoing ESPT is usually solvent-, isotope-, and buffer-ion sensitive, and in some systems the ESPT can be promoted by environmental factors, e.g., the presence of buffer ions. This sensitivity to the microenvironment parameters makes the ESPT systems potentially useful for biological applications.

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Section: 6-diamino-8-azapurine and The Corresponding Ribosidesmentioning

confidence: 99%

Excited-State Proton Transfer and Phototautomerism in Nucleobase and Nucleoside Analogs: A Mini-Review

Wierzchowski¹

2014

Nucleosides, Nucleotides and Nucleic Acids

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“…[17,18] Therefore, the incorporation of Z G instead of guanine into β-peptide 14helices should suppress higher aggregation due to Hoogsteen pairing of guanine. [19] In addition, the incorporation of Z G as a guanine analog into double strands diminishes the double-strand stability if guanine recognition on the Hoogsteen site is required. A comparison of guanine-and Z G-containing oligomers might allow conclusions to be drawn on the preferred guanine-pairing mode in β-peptide double strands.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a 7‐Deazaguanine‐Functionalized β‐Amino Acid: Improved Specificity of β‐Peptide Helix Organization

2006

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Nucleobase‐functionalized β‐peptides are a suitable scaffold for the construction of well‐defined tertiary structures organized by nucleobase pair recognition. Since guanine‐rich oligomers are especially known to form higher aggregates, an enantiomerically pure 7‐deazaguanine (zG)‐functionalized nucleo‐β3‐amino acid was synthesized from a β‐lactam derivative as a key intermediate. Incorporated into β‐peptide 14‐helices it was possible to reduce aggregation phenomena and to increase recognition selectivity. Evidence for base‐pair‐mediated helix recognition was obtained by temperature‐dependent UV and CD spectroscopy. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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“…The glycosylation reactions then proceeded smoothly. Nucleosides derived from sugars 13b, 13 13d, 14 and 13f 15 by virtue of lacking a protected 3¢-hydroxyl gave a mixture of anomers as anticipated. The a/b anomers were separated by chromatography and the stereochemistry determined by comparison of the 1 H NMR's to analogus purine nucleosides for the same sugars.…”

Section: Figurementioning

confidence: 83%

Synthesis of Novel 2-Cyano-7-deaza-8-azapurine- and 2-Cyano-8-azapurine-Derived Nucleosides

Wainwright¹,

Maddaford²,

Simms³

et al. 2011

Synlett

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A novel systematic approach to the synthesis of 2-cyano-7-deaza-8-azapurine derived nucleosides is described. It is shown how this chemistry was developed with the labile 2-substituted nitrile position in mind, and also how the same approach is applicable to 2-cyano-8-azapurine derived nucleosides.Nucleosides and their analogues continue to be investigated to treat a range of diseases including cancer and viral infections. 1 In addition, nucleosides and nucleotides form the primary building blocks for the construction of natural and modified genetic material. For example, oligomeric nucleoside constructs form the basis of antisense/RNA interference applications. 2 Finally, nucleosides are intimately involved in key processes such as metabolic regulation and energy storage. 3 A large body of synthetic methodology to access modified bases and riboses has accumulated over the last several decades, 4 spurred along by several highly successful drugs in this class. 5 Research in this area is complicated by a requirement that the nucleoside must be converted into its triphosphate in cellular assays followed by effective inhibition of the target in the designated pathway. Lack of biological activity due to poor or no recognition by the cellular kinases required to activate the parent nucleoside is often a high hurdle to overcome. The effect of structural modifications on the conformational preference of nucleoside analogues has been proposed as a significant driver of subsequent recognition by biological systems. 6 Two strong drivers in nucleoside design include a desire to stay close in structure to the natural bases and riboses, while designing novelty into target compounds.With these considerations in mind, we became interested in 2-cyano-8-aza-7-deazapurines ( Figure 1) as a potential adenine mimic by virtue of a replacement of the C2-hydrogen of adenine with CN and an isomeric movement of N7 to C8. 7 Figure 1

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8‐Aza‐2′‐deoxyguanosine and Related 1,2,3‐Triazolo[4,5‐d]pyrimidine 2′‐Deoxyribofuranosides

Cited by 25 publications

References 15 publications

Excited-State Proton Transfer and Phototautomerism in Nucleobase and Nucleoside Analogs: A Mini-Review

Excited-State Proton Transfer and Phototautomerism in Nucleobase and Nucleoside Analogs: A Mini-Review

Synthesis of a 7‐Deazaguanine‐Functionalized β‐Amino Acid: Improved Specificity of β‐Peptide Helix Organization

Synthesis of Novel 2-Cyano-7-deaza-8-azapurine- and 2-Cyano-8-azapurine-Derived Nucleosides

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