This work deals with the synthesis of a new nitrogen mustard derivative based on thymine. To introduce the bis(2-chloroethyl)amine group to position 4 of the pyrimidine base, many strategies were explored and the desired compound was finally obtained, thanks to a synthetic pathway in five steps.
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Willardiine and Its Synthetic Analogues: Biological Aspects and Implications in Peptide Chemistry of This Nucleobase Amino Acid.
Pharmaceuticals (Basel)
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Institute of Biostructures and Bioimaging-Italian National Council for Research (IBB-CNR), Via De Amicis 95, 80145 Naples, Italy.
Willardiine is a nonprotein amino acid containing uracil, and thus classified as nucleobase amino acid or nucleoamino acid, that together with isowillardiine forms the family of uracilylalanines isolated more than six decades ago in higher plants. Willardiine acts as a partial agonist of ionotropic glutamate receptors and more in particular it agonizes the non-N-methyl-D-aspartate (non-NMDA) receptors of L-glutamate: ie. the α-amino-3-hydroxy-5-methyl-4-isoxazole-propionic acid (AMPA) and kainate receptors.
View Article and Find Full Text PDFRational magnetic modification of N,N-dioxidized pyrazine ring expanded adenine and thymine: a diradical character induced by base pairing and double protonation.
Phys Chem Chem Phys
September 2019
School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100, People's Republic of China.
Rational modification of biomolecules especially DNA base pairs for the theoretical design of molecular magnets has attracted extensive interest. In this work, we report a modification strategy for adenine/thymine-based magnets through introducing a N,N-dioxidized pyrazine ring to either adenine or thymine to form ring-expanded bases (noA/noT) based on their experimentally synthesized derivatives. Further functionalization is conducted by double protonation and pairing with a normal complementary base (nohA-T/nohT-A), respectively.
View Article and Find Full Text PDFNew thymine-based derivative of nitrogen mustards.
Nucleosides Nucleotides Nucleic Acids
June 2012
Laboratoire de Chimie des Substances Naturelles EA1069, Faculté des Sciences et Techniques, Limoges, France.
This work deals with the synthesis of a new nitrogen mustard derivative based on thymine. To introduce the bis(2-chloroethyl)amine group to position 4 of the pyrimidine base, many strategies were explored and the desired compound was finally obtained, thanks to a synthetic pathway in five steps.
View Article and Find Full Text PDF4-Aminobenzimidazole-1-methylthymine: a model for investigating Hoogsteen base-pairing between adenine and thymine.
J Phys Chem A
October 2011
Institut für Physikalische und Theoretische Chemie, Goethe-Universität, Frankfurt/Main, Germany.
We report the infrared spectrum of the 4-aminobenzimidazole-1-methylthymine (4ABI:1MT) heterodimer, detected by femtosecond multiphoton ionization. Based on calculations of both the harmonic and the anharmonic frequencies, the observed vibrational spectrum is assigned to a structure that mimics the Hoogsteen base pairing of adenine and thymine. A notable observation made in the course of this study is that there is a significant imbalance in the observed strengths of the H-bonds.
View Article and Find Full Text PDFNucleobase-mediated stereospecific radical polymerization and combination with RAFT polymerization for simultaneous control of molecular weight and tacticity.
Macromol Rapid Commun
January 2011
Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa-ku, Nagoya 464-8603, Japan.
A highly soluble thymine-based compound (1-octyl thymine), having an array of hydrogen bonding sites with an ADA sequence (A and D: proton acceptor and donor sites, respectively), was used to mediate the stereospecific radical polymerization of an acrylamide monomer [N-(6-acetamidopyridin-2-yl)acrylamide] possessing the complementary DAD sequence. The thymine derivative interacted with the monomer via the selective 1:1 and strong triple hydrogen-bonding interaction (K = 1.1 × 10(3) in CHCl(3) at 20 °C) and mediated the syndiospecific radical polymerization of the monomer to give syndiotactic rich polymers up to r = 84% in CH(2)Cl(2) at -78 °C.
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