- Cytidine and ribothymidine nucleolipids synthesis, organogelation, and selective anion and metal ion responsiveness
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Extending the functional utility of nucleolipids to natural nucleosides such as cytidine and ribothymidine would facilitate the development of supramolecular gels and responsive smart materials. We have reported long-acyl chain conjugated novel cytidine and ribothymidine nucleolipids. It is known that small chemical variations result in significant differences in the self-assembling processes of nucleolipids. When the fatty acid acyl chain is attached onto the cytidine (diacylated) or ribothymidine (triacylated) it does not support organogelation. But diacylated ribothymidines produce stable organogels in various organic solvents, ranging from polar to non-polar solvents. Further, single-crystal and 1H NMR analysis indicated that multiple H-bonding, CH-π, hydrophobic effects and solvent-mediated interactions are the main driving forces for the organogelation. These supramolecular gels show a selective responsive behavior with respective fluoride and mercury ions by gel to sol phase transitions. Unusual mercury mediated base pairing through sugar residues (sugar-Hg2+-sugar) and also mercury specificity for nucleolipid 7d in the presence of mixture of toxic metal ions have been thoroughly investigated.
- Nuthanakanti, Ashok
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- Synthesis and Multiple Incorporations of 2′-O-Methyl-5-hydroxymethylcytidine, 5-Hydroxymethylcytidine and 5-Formylcytidine Monomers into RNA Oligonucleotides
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The synthesis of 2′-O-methyl-5-hydroxymethylcytidine (hm5Cm), 5-hydroxymethylcytidine (hm5C) and 5-formylcytidine (f5C) phosphoramidite monomers has been developed. Optimisation of mild post-synthetic deprotection conditions enabled the synthesis of RNA containing all four naturally occurring cytosine modifications (hm5Cm, hm5C, f5C plus 5-methylcytosine). Given the considerable interest in RNA modifications and epitranscriptomics, the availability of synthetic monomers and RNAs containing these modifications will be valuable for elucidating their biological function(s).
- Tanpure, Arun A.,Balasubramanian, Shankar
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- Tightly linked morpholino-nucleoside chimeras: new, compact cationic oligonucleotide analogues
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The polyanionic phosphodiester backbone of nucleic acids contributes to high nuclease sensitivity and low cellular uptake and is therefore a major obstacle to the biological application of native oligonucleotides. Backbone modifications, particularly charge alterations is a proven strategy to provide artificial oligonucleotides with improved properties. Here, we describe the synthesis of a new type of oligonucleotide analogues consisting of a morpholino and a ribo- or deoxyribonucleoside in which the 5′-amino group of the nucleoside unit provides the nitrogen of the morpholine ring. The synthetic protocol is compatible with trityl and dimethoxytrityl protecting groups and azido functionality, and was extended to the synthesis of higher oligomers. The chimeras are positively charged in aqueous medium, due to theN-alkylated tertiary amine structure of the morpholino unit.
- Batta, Gyula,Bege, Miklós,Bereczki, Ilona,Borbás, Anikó,Debreczeni, Nóra,Herczeg, Mihály,Herczegh, Pál
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supporting information
p. 8711 - 8721
(2021/10/22)
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- SYNTHESIS OF BACKBONE MODIFIED MORPHOLINO OLIGONUCLEOTIDES AND CHIMERAS USING PHOSPHORAMIDITE CHEMISTRY
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Amine substituted morpholino oligonucleotides, other than the classical N,N-dimethylamino PMO analogue, and methods of efficiently synthesizing these oligonucleotides with high yield are provided. Morpholino oligonucleotides having thiophosphoramidate, ph
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- Synthesis and properties of morpholino chimeric oligonucleotides
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Chimeric oligonucleotides with the novel morpholino modification and the phosphoramidate linkers have been synthesized and characterized. These oligonucleotides showed moderate thermal stability with complementary RNA and DNA, and enhanced resistance towa
- Zhang, Nan,Tan, Chunyan,Cai, Puqin,Jiang, Yuyang,Zhang, Peizhuo,Zhao, Yufen
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p. 3570 - 3573
(2008/09/21)
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- 2'-O,5-dimethyluridine: A total synthesis and single crystal X-ray diffraction study
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A new method for the synthesis of 2'-O,5-dimethyluridine (5) has provided the title compound in a higher yield. Application of a one-pot ribosylation methodology resulted in an efficient, high yield synthesis of 5-methyluridine (ribothymine, 3b). An X-ray diffraction analysis of 5 disclosed the conformation of the sugar moiety of this nucleoside as anti, N(3'-endo), g+.
- Lewis,Revankar,Hogan
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p. 1309 - 1316
(2007/10/02)
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- 1-(2,3-anhydro-β-D-lyxofuranosyl)cytosine derivatives as potential inhibitors of the human immunodeficiency virus
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We report here that 1-(2,3-anhydro-β-D-lyxofuranosyl)cytosine has activity against the human immunodeficiency virus in vitro. A number of 2',3'-anhydro-β-D-lyxofuranosyl nucleoside derivatives were prepared, but none had the activity of the title compound. New efficient procedures were developed for the synthesis of 3'-deoxy-3'-alkyl- and 3'-deoxy-β-D-arabinosylpyrimidine derivatives.
- Webb,Mitsuya,Broder
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p. 1475 - 1479
(2007/10/02)
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