ISBN 978-3-8439-3460-2

978-3-8439-3460-2, Reihe Organische Chemie

Julia Carola Schneider
8-Vinyl Guanine - A Fluorescent Probe and Tool for Nucleoside-Peptide-Conjugation

210 Seiten, Dissertation Georg-August-Universität Göttingen (2017), Softcover, A5

Zusammenfassung / Abstract

Fluorescent probes are widely used in various fields of life sciences and their trend is moving towards fluorescent properties caused by substitution or minimal interference with natural occurring systems. In the present thesis, the previously reported fluorescent nucleobase 8-Vinyl guanine was used as an anchor for so called click reactions, which are becoming increasingly important in biological and pharmaceutical chemistry as well. The additional vinyl group in position eight of the nucleobase, which causes minimal change in the natural structure of guanine, leads to fluorescent properties. Therefore, the vinylated analogs of guanosine and 2’-deoxyguanosine as well as modified oligonucleotides were used as an anchor for a variety of click reactions, including cycloadditions and thiol-ene reactions. The obtained results are discussed within this work.

Small messenger molecules play important roles in cells, since they are responsible for communication inside cells. For a more detailed understanding of these communication processes, fluorescent probes can be used as a useful tool for minimal interference with the biological system. The focus in the last chapter is on the syntheses of two fluorescent second messengers bearing additional vinyl groups in position eight.