Oligonucleotides Containing 1-Aminomethyl or 1-Mercaptomethyl-2-deoxy-d-ribofuranoses: Synthesis, Purification, Characterization, and Conjugation with Fluorophores and Lipids
Open Access
- 5 February 2021
- journal article
- research article
- Published by American Chemical Society (ACS) in Bioconjugate Chemistry
- Vol. 32 (2) , 350-366
Abstract
Oligonucleotide conjugates are widely used as therapeutic drugs, gene analysis, and diagnostic tools. A critical step in the biologically relevant oligonucleotide conjugates is the design and synthesis of functional molecules that connect oligonucleotide with ligands. Here, we report the synthesis and application for oligonucleotide functionalization of novel tethers based on aminomethyl and mercaptomethyl sugar derivatives. Starting from a common cyano sugar precursor, three novel phosphoramidites have been prepared in the two α- and β-anomeric forms. The mercaptomethyl sugar was protected with the S-acetyl group, while two different protecting groups have been developed for the aminomethyl sugar. These two protecting groups are orthogonal, as they can be removed independently using photolysis or ammonolysis. This combination allowed the introduction of two different ligands in a single oligonucleotide.Keywords
Funding Information
- Departament d'Innovaci?, Universitats i Empresa, Generalitat de Catalunya (2017SGR114)
- Ministerio de Ciencia e Innovaci?n (CTQ2014-55015-P, CTQ2017-84415-R)
- Centro de Investigaci?n Biom?dica en Red en Bioingenier?a, Biomateriales y Nanomedicina (CB06_0019)
- Gobierno del Principado de Asturias (IDI/2018/000181)
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