Recent synthesis of thietanes

• Jiaxi Xu

Beilstein J. Org. Chem. 2020, 16, 1357–1410, doi:10.3762/bjoc.16.116

Glycosylation reactions mediated by hypervalent iodine: application to the synthesis of nucleosides and carbohydrates

• Yuichi Yoshimura,
• Hideaki Wakamatsu,
• Yoshihiro Natori,
• Yukako Saito and
• Noriaki Minakawa

Beilstein J. Org. Chem. 2018, 14, 1595–1618, doi:10.3762/bjoc.14.137

• described the potent antiherpesvirus activity of 2’-deoxy-4’-thionucleoside 2, in which sulfur was introduced in place of the sugar ring oxygen of 2’-deoxynucleoside. The results for 2’-substituted nucleosides and 2’-deoxy-4’-thionucleosides strongly suggested that 2’-substituted 4’-thionucleosides would be

• its α-anomer [27][28] (Scheme 1). After we reported the synthesis of 4’-thioDMDC using a Pummerer-type glycosylation reaction, Minakawa and Matsuda applied the reaction to the syntheses of 4’-thioribonucleosides. Applying the synthetic scheme of 2’-deoxy-4’-thionucleoside by Walker to a ribo

• ’-thionucleoside derivatives by other groups and became a standard approach for the glycosylation [33][34][35][36][37]. On the other hand, the conversion from the sulfide to 4’-thionucleoside using the Pummerer-type glycosylation included an oxidation step. If the oxidation of sulfide 31 and the Pummerer-type

Mechanochemistry of nucleosides, nucleotides and related materials

• Olga Eguaogie,
• Joseph S. Vyle,
• Patrick F. Conlon,
• Manuela A. Gîlea and
• Yipei Liang

Beilstein J. Org. Chem. 2018, 14, 955–970, doi:10.3762/bjoc.14.81

• for nucleoside and nucleotide chemistry as, although considerably cheaper, leaching of iron from stainless steel vessels in the presence of sulfur-containing materials [21] has been found to inhibit the preparation of thionucleoside [22] or thionucleotide [23] analogues. Although grinding using PTFE

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

• attributed to the reduction of the thiocarbonyl group, (C4=S) (Figure 3, solid black line). In particular, as reported in [37] about the electrochemical properties of some thiones, the redox process involving the thionucleoside could be attributable to an electron transfer process centered on the C=S moiety

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

• been described in the literature, but most of them fall short of at least one of the above criteria. We developed an efficient method to site-specifically and reversibly cross-link thionucleoside base pairs in synthetic duplex oligodeoxynucleotides by bisalkylation with 1,2-diiodoethane resulting in an

• ; DNA methyltransferase; nucleic acids; oligodeoxynucleotide; thionucleoside; Introduction Covalent interstrand DNA cross-links have long sparked clinical and biochemical interest. The cytotoxicity of bisfunctional alkylating agents like nitrogen mustards or chloroethyl nitrosourea (CENU) derivatives

• contacts between the proteins and their DNA targets that are formed before the target base is flipped or strands are separated. Conclusion In conclusion, we have developed a new efficient method to site-specifically and reversibly cross-link thionucleoside base pairs in duplex DNA via an ethylene bridge