Applications of bio-orthogonal tools towards RNA synthesis and imaging of RNA

Date of Award

1-1-2019

Language

English

Document Type

Dissertation

Degree Name

Doctor of Philosophy (PhD)

College/School/Department

Department of Chemistry

Content Description

1 online resource (xiv, 155 pages) : illustrations.

Dissertation/Thesis Chair

Maksim Royzen

Committee Members

Rabi Musah, Jia Sheng, Thomas Begley

Keywords

Oligonucleotide Chemistry, Organic Synthesis, RNA Synthesis, Solid Phase Synthesis, Bioconjugates, RNA, Diels-Alder reaction, Tetrazine, Fluorescence microscopy

Subject Categories

Chemistry

Abstract

This thesis describes several applications of the bio-orthogonal inverse electron demand Diels-Alder reaction between trans-cyclooctene and tetrazine. The two functional groups are highly selective for each other and the reaction proceeds in high yield in organic solvents, water, cell media and cell lysate. One application focuses on site-specific fluorescence labeling of RNA. We developed methodology to incorporate the trans-cyclooctene group into RNA strands by in vitro transcription. Subsequent fluorescent labelling has been achieved using fluorescein-modified tetrazine. This approach has been illustrated using a model RNA strand, miR-122.

Comments

Requested ProQuest takedown; no end date

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