Journal
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
Volume 21, Issue 14, Pages -Publisher
MDPI
DOI: 10.3390/ijms21145127
Keywords
RNA; chemical synthesis of RNA; TC-protecting group; 2 ' hydroxyl; selective deprotection; solid-phase synthesis; postsynthetic modification
Funding
- Austrian Science Fund (FWF) [M2517, AAAA-A17-117020210021-7]
- Austrian Science Fund (FWF) [M2517] Funding Source: Austrian Science Fund (FWF)
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We report a universal straightforward strategy for the chemical synthesis of modified oligoribonucleotides containing functional groups of different structures at the 2 ' position of ribose. The on-column synthetic concept is based on the incorporation of two types of commercial nucleotide phosphoramidites containing orthogonal 2 '-O-protecting groups, namely 2 '-O-thiomorpholine-carbothioate (TC, as permanent) and 2 '-O-tert-butyl(dimethyl)silyl (tBDMS, as temporary), to RNA during solid-phase synthesis. Subsequently, the support-bound RNA undergoes selective deprotection and follows postsynthetic 2 ' functionalization of the naked hydroxyl group. This convenient method to tailor RNA, utilizing the advantages of solid phase approaches, gives an opportunity to introduce site-specifically a wide range of linkers and functional groups. By this strategy, a series of RNAs containing diverse 2 ' functionalities were synthesized and studied with respect to their physicochemical properties.
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