Novel Convenient Approach to the Solid-Phase Synthesis of Oligonucleotide Conjugates
1
Institute of Chemical Biology and Fundamental Medicine SB RAS, Lavrentiev ave.8, Novosibirsk 630090, Russia
2
Department of Natural Sciences, Novosibirsk State University, Pirogova str.2, Novosibirsk 630090, Russia
*
Author to whom correspondence should be addressed.
Academic Editor: Yoshiyuki Hari
Molecules 2019, 24(23), 4266; https://doi.org/10.3390/molecules24234266
Received: 1 November 2019 / Revised: 19 November 2019 / Accepted: 20 November 2019 / Published: 22 November 2019
(This article belongs to the Special Issue Recent Development of Nucleic Acid Analogs)
A novel and convenient approach for the solid-phase 5′-functionalization of oligonucleotides is proposed in this article. The approach is based on the activation of free 5′-hydroxyl of polymer support-bound protected oligonucleotides by N,N′-disuccinimidyl carbonate followed by interaction with amino-containing ligands. Novel amino-containing derivatives of closo-dodecaborate, estrone, cholesterol, and α-tocopherol were specially prepared. A wide range of oligonucleotide conjugates bearing closo-dodecaborate, short peptide, pyrene, lipophilic residues (cholesterol, α-tocopherol, folate, estrone), aliphatic diamines, and propargylamine were synthesized and characterized to demonstrate the versatility of the approach. The developed method is suitable for the conjugate synthesis of oligonucleotides of different types (ribo-, deoxyribo-, 2′-O-methylribo-, and others).
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Keywords:
oligonucleotide conjugates; solid-phase 5′-functionalization; N,N′-disuccinimidyl carbonate (DSC); amino ligands; boron clusters
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MDPI and ACS Style
Meschaninova, M.I.; Novopashina, D.S.; Semikolenova, O.A.; Silnikov, V.N.; Venyaminova, A.G. Novel Convenient Approach to the Solid-Phase Synthesis of Oligonucleotide Conjugates. Molecules 2019, 24, 4266.
AMA Style
Meschaninova MI, Novopashina DS, Semikolenova OA, Silnikov VN, Venyaminova AG. Novel Convenient Approach to the Solid-Phase Synthesis of Oligonucleotide Conjugates. Molecules. 2019; 24(23):4266.
Chicago/Turabian StyleMeschaninova, Mariya I.; Novopashina, Darya S.; Semikolenova, Olga A.; Silnikov, Vladimir N.; Venyaminova, Alya G. 2019. "Novel Convenient Approach to the Solid-Phase Synthesis of Oligonucleotide Conjugates" Molecules 24, no. 23: 4266.
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