- Exploration of charge-transfer solids utilizing nucleobases: Nanoarchitectures by hydrogen-bonds in the ionic assemblies of guanine and TCNQ derivatives
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We studied formation and structural characteristics of charge-transfer solids of 9-n-butylguanine (BuG) with fluorinated tetracyanoquinodimethane derivatives (FnTCNQ, n = 4, 2, and 1). Complex formation in a methanol (MeOH)-containing solvent generated two types of salts composed of either a methoxy-substituted anion or a fully ionic anion radical of F nTCNQ. In all anion radical salts, BuG existed as a protonated or a hemiprotonated species, BuGH+ or (BuG)(BuGH+), respectively, and formed hydrogen-bonded (H-bonded) assemblies. In these BuGH+ assemblies, FnTCNQ?- molecules were fixed and aligned periodically, providing H-bonded polycationic templates. In (BuGH+)(F4TCNQ?-), BuGH+ dimers by complementary H-bonds formed a two-dimensional (2D) polycationic sheet. The F4TCNQ?- face-to-face dimers formed a one-dimensional (1D) segregated column aided by formation of H-bonds with BuGH+. In (BuGH+)(F2TCNQ?-)(MeOH), BuGH+ dimers by complementary double H-bonds formed a 1D polycationic ribbon supported by MeOH-mediated H-bonds. A 1D mixed stack column of (BuGH+) 2 and (F2TCNQ?-)2 dimers was formed owing to their complementary geometry and size. In (BuG)(BuGH +)(F1TCNQ?-), a new type of BuG-BuGH + pair formed a 1D ribbon supported by complementary H-bonds, and F1TCNQ?- dimers were aligned by H-bonds with the BuG-BuGH+ ribbon.
- Murata, Tsuyoshi,Saito, Gunzi,Nakamura, Kenji,Maesato, Mitsuhiko,Hiramatsu, Takaaki,Yoshida, Yukihiro
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- Concise access to N9-mono-, N2-mono- and N2,N9-di-substituted guanines via efficient Mitsunobu reactions
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Guanine poses several problems to the synthetic chemist owing to its polyfunctional nature and poor solubility. Over the past few decades, synthetic guanines have found applications as anti-cancer and anti-viral agents. Coupled with the ever-growing inter
- Fletcher, Steven,Shahani, Vijay M.,Lough, Alan J.,Gunning, Patrick T.
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experimental part
p. 4621 - 4632
(2010/07/06)
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- Mitsunobu coupling of nucleobases and alcohols: An efficient, practical synthesis for novel nonsugar carbon nucleosides
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(Chemical Equation Presented) A simple facile synthesis of substituted purine derivatives has been developed by using Mitsunobu conditions for an alcohol and a respective nucleobase. A wide range of alcohols produces good to excellent yield (>90%). The resulting purine analogues show good regioselectivity with N-9 substitution as the dominant products in most of the cases. Application of diastereospecific alcohols reveals a complete inversion of the carbon stereogenic center giving a single diastereomer. More than two dozen novel nucleobase derivatives have been prepared in high yield.
- Lu, Weibing,Sengupta, Sujata,Petersen, Jeffrey L.,Akhmedov, Novruz G.,Shi, Xiaodong
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p. 5012 - 5015
(2008/02/07)
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- Alkylpurines as immunopotentiating agents. Synthesis and antiviral activity of certain alkylguanines.
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Several simple 8-substituted 9-alkyl- and 7,8-disubstituted 9-alkylguanine derivatives were synthesized as potential antiviral agents. These were tested for antiviral protection against a lethal Semliki Forest virus (SFV) infection in mice, and their anti
- Michael,Cottam,Smee,Robins,Kini
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p. 3431 - 3436
(2007/10/02)
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- ALKYLATION OF 6-METHYLTHIO- AND 6-BENZYLOXYGUANINE UNDER PHASE-TRANSFER CONDITIONS
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Phase-transfer-catalyzed alkylation of 6-methylthio- and 6-benzyloxyguanine followed by acid hydrolysis provides a simple procedure for the preparation of various 9- and 7-substituted guanines.
- Ramzaeva, N.,Alksnis, E.,Goldberg, Yu.,Lidaks, M.
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p. 3121 - 3128
(2007/10/02)
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