Artificial bioconjugates with naturally occurring linkages: the use of phosphodiester

• Takao Shoji,
• Hiroki Fukutomi,
• Yohei Okada and
• Kazuhiro Chiba

Beilstein J. Org. Chem. 2018, 14, 1946–1955, doi:10.3762/bjoc.14.169

• elaborate bioconjugates. Herein, we describe the use of a phosphodiester bond as a versatile option to access various bioconjugates. An opposite activation strategy, involving 5’-phosphitylation of the supported oligonucleotides, has allowed several biomolecules that possess an unactivated alcohol to be

• linkage. Described herein is a simple and straightforward access to artificial bioconjugates with naturally occurring linkages. Results and Discussion The present work began with the optimization of the reaction conditions for the activation of the 5’-terminus, more specifically, 5’-phosphitylation [74

• of the starting material (Table 1, entries 1–3). The best result was obtained at 25 mM concentration in dichloromethane (CH2Cl2). Although tetrahydrofuran (THF) is one of the typical reaction solvents for ACSS-assisted liquid-phase synthesis, this was not the case for the 5’-phosphitylation (Table 1

Preparation of trinucleotide phosphoramidites as synthons for the synthesis of gene libraries

• Ruth Suchsland,
• Bettina Appel and
• Sabine Müller

Beilstein J. Org. Chem. 2018, 14, 397–406, doi:10.3762/bjoc.14.28

• to 49% [23]. 5. Phosphitylation and coupling of trinucleotide synthons in solid phase DNA synthesis To be used as building blocks in standard phosphoramidite synthesis, fully protected trimers need to be converted in phosphoramidites (Figure 7). This has been described in a number of reports [19][22