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Novel Convenient Approach to the Solid-Phase Synthesis of Oligonucleotide Conjugates.

ABSTRACT: 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 ?-tocopherol were specially prepared. A wide range of oligonucleotide conjugates bearing closo-dodecaborate, short peptide, pyrene, lipophilic residues (cholesterol, ?-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).

SUBMITTER: Meschaninova MI

PROVIDER: S-EPMC6930482 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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Novel Convenient Approach to the Solid-Phase Synthesis of Oligonucleotide Conjugates.

Meschaninova Mariya I MI Novopashina Darya S DS Semikolenova Olga A OA Silnikov Vladimir N VN Venyaminova Alya G AG

Molecules (Basel, Switzerland) 20191122 23

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 con ...[more]

PMID: 31771111

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