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Water-Soluble Leaving Group Enables Hydrophobic Functionalization of RNA.

ABSTRACT: Attachment of hydrophobic groups to RNA is challenging because of their poor aqueous solubility. One-step acylation of RNA 2'-OH groups in water using a water-soluble imidazole leaving group is described. The effect of the hydrophobic groups on hybridization is reported. Furthermore, propargyl-functionalized RNA is shown to be readily labeled with a fluorophore. Lastly, heptyl-functionalized RNA is found to exhibit the unusual property of solubility in organic solvents.

SUBMITTER: Velema WA

PROVIDER: S-EPMC6478029 | biostudies-literature | 2018 Oct

REPOSITORIES: biostudies-literature

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Water-Soluble Leaving Group Enables Hydrophobic Functionalization of RNA.

Velema Willem A WA Kool Eric T ET

Organic letters 20181009 20

Attachment of hydrophobic groups to RNA is challenging because of their poor aqueous solubility. One-step acylation of RNA 2'-OH groups in water using a water-soluble imidazole leaving group is described. The effect of the hydrophobic groups on hybridization is reported. Furthermore, propargyl-functionalized RNA is shown to be readily labeled with a fluorophore. Lastly, heptyl-functionalized RNA is found to exhibit the unusual property of solubility in organic solvents. ...[more]

PMID: 30299958

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