Synthesis of 1,4-azaphosphinine nucleosides and evaluation as inhibitors of human cytidine deaminase and APOBEC3A

• Maksim V. Kvach,
• Stefan Harjes,
• Harikrishnan M. Kurup,
• Geoffrey B. Jameson,
• Elena Harjes and
• Vyacheslav V. Filichev

Beilstein J. Org. Chem. 2024, 20, 1088–1098, doi:10.3762/bjoc.20.96

• ssDNA. Results and Discussion Synthesis of nucleosides It is more straightforward to start the synthesis of a modified nucleoside from the assembly of a nucleobase that can be coupled to the sugar afterwards using the Hilbert–Johnson reaction or a silyl variation of it as described in the literature [65

Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

• Umesh P. Aher,
• Dhananjai Srivastava,
• Girij P. Singh and
• Jayashree B. S

Beilstein J. Org. Chem. 2021, 17, 2680–2715, doi:10.3762/bjoc.17.182

• in the corresponding analogues of ᴅ- and ʟ-configured nucleosides and other unnatural nucleoside derivatives [16][17][18][19]. Therefore, further demand for various effective chemical syntheses of these nucleoside analogues is rapidly growing. The FDA has approved modified nucleoside analogues such

Double-headed nucleosides: Synthesis and applications

• Vineet Verma,
• Jyotirmoy Maity,
• Vipin K. Maikhuri,
• Ritika Sharma,
• Himal K. Ganguly and
• Ashok K. Prasad

Beilstein J. Org. Chem. 2021, 17, 1392–1439, doi:10.3762/bjoc.17.98

• sugar [3][4]. The synthetic accessibility of these organic molecules encouraged researchers to prepare sugar-modified nucleosides [5][6] and nucleobase-modified nucleosides [7][8]. Modified nucleoside monomers comprising more than one nucleobase are called double-headed nucleosides [9][10]. A thorough

Beyond ribose and phosphate: Selected nucleic acid modifications for structure–function investigations and therapeutic applications

• Christopher Liczner,
• Kieran Duke,
• Gabrielle Juneau,
• Martin Egli and
• Christopher J. Wilds

Beilstein J. Org. Chem. 2021, 17, 908–931, doi:10.3762/bjoc.17.76

• by way of an HCV polymerase and extended to give a full-length oligonucleotide product, whereas 2',4'-diF-rUTP inhibited RNA synthesis at the early stages of dinucleotide-primed reactions [206]. Standard solid-phase synthesis allowed for the incorporation of this modified nucleoside into both RNA and

Interactions between 4-thiothymidine and water-soluble cyclodextrins: Evidence for supramolecular structures in aqueous solutions

• Vito Rizzi,
• Sergio Matera,
• Paola Semeraro,
• Paola Fini and
• Pinalysa Cosma

Beilstein J. Org. Chem. 2016, 12, 549–563, doi:10.3762/bjoc.12.54

• described in [18], the preparation of simple physical mixtures with CDs was already shown to be effective in terms of protective activity. Starting from these considerations, the main goal of this work is to study the ability of the modified nucleoside S4TdR to form inclusion complexes with five CDs: 2-HP-α

Versatile synthesis and biological evaluation of novel 3’-fluorinated purine nucleosides

• Hang Ren,
• Haoyun An,
• Paul J. Hatala,
• William C. Stevens Jr,
• Jingchao Tao and
• Baicheng He

Beilstein J. Org. Chem. 2015, 11, 2509–2520, doi:10.3762/bjoc.11.272

• nucleosides have limited the synthesis and biological testing of these promising fluorine modified nucleoside derivatives. To open up research and therapeutic exploration of this class of compounds, we developed efficient synthetic routes for the construction of 3’-deoxy-3’-fluoroadenosine and guanosine

• -modified nucleoside derivatives, and it was utilized for the synthesis of all analogues reported herein. This strategy avoids tedious orthogonal protecting group manipulations previously reported in literature [31][32][33][34][35]. Our strategy provides the desired nucleoside intermediates and also opens

Versatile synthesis of amino acid functionalized nucleosides via a domino carboxamidation reaction

• Vicky Gheerardijn,
• Jos Van den Begin and
• Annemieke Madder

Beilstein J. Org. Chem. 2014, 10, 2566–2572, doi:10.3762/bjoc.10.268

• Scheme 3. Protected lysine 10 is commercially available and was coupled with the TBDMS-protected nucleoside 1 to afford product 11 in high yield. After deprotection of the tert-butyldimethylsilyl protecting groups using the above described protocol, modified nucleoside 12 could be selectively protected

Reversibly locked thionucleobase pairs in DNA to study base flipping enzymes

• Christine Beuck and
• Elmar Weinhold

Beilstein J. Org. Chem. 2014, 10, 2293–2306, doi:10.3762/bjoc.10.239

• opposing adenine, resulting in ring opening and formation of an ethylene cross-linked base pair [29][30]. Other aziridine-substituted nucleobases have been incorporated enzymatically by a DNA polymerase, but elongation past the modified nucleoside has not been reported [31]. Another approach uses

Synthesis of a bifunctional cytidine derivative and its conjugation to RNA for in vitro selection of a cytidine deaminase ribozyme

• Nico Rublack and
• Sabine Müller

Beilstein J. Org. Chem. 2014, 10, 1906–1913, doi:10.3762/bjoc.10.198

• derivative suitable for conjugation to RNA and linkage of the conjugated library to a streptavidine-coated surface. Successful conjugation of the cytidine derivative to the 3'-terminus of a model RNA is demonstrated. Keywords: cytidine deaminase; modified nucleoside; nucleic acids; ribozyme; RNA world

• -position of 3 in order to attach a biotin unit to the modified nucleoside. Linker 4 was synthesized from 2,2’-(ethylenedioxy)diethylamine (8) with di-tert-butyl dicarbonate (Boc2O) in dioxane [35] (Figure 3). The mono protected diamino linker 4 was purified by chromatography on silica gel and subsequently

Diarylethene-modified nucleotides for switching optical properties in DNA

• Sebastian Barrois and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2012, 8, 905–914, doi:10.3762/bjoc.8.103

• diarylethene-modified nucleoside 4 then continues by cleavage of the TMS protecting group of 11 with K2CO3 in MeOH. Finally, the synthesis is concluded by the Sonogashira-type coupling of diarylethene 13 to 5-iodo-2’-deoxyuridine (14) in 65% yield. For the second and third modified nucleosides 5 and 6, the

• 310 nm cannot be performed in an efficient way. This result is in contrast to that for the first diarylethene-modified nucleoside 4 described above and limits the applicability of nucleoside 5 significantly as a photochromic switch in nucleic acids. The diarylethene 5 can be switched several times

The C–F bond as a conformational tool in organic and biological chemistry

• Luke Hunter

Beilstein J. Org. Chem. 2010, 6, No. 38, doi:10.3762/bjoc.6.38

• amount of research into fluorinated nucleoside analogues as potential treatments for cancer and viral infection [21][22]. Fluorine is an obvious choice for incorporating into sugar-modified nucleoside analogues, since fluorine can be considered a reasonable mimic of either a hydrogen atom or a hydroxyl