Beilstein J. Org. Chem.2018,14, 114–129, doi:10.3762/bjoc.14.7
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Keywords: B-to-Z-DNA transition; fluorescent base analogues; FRET; netropsin; nucleic acid structure and dynamics; quadracyclic adenines; tricycliccytosines; Z-DNA; Review
Introduction
The importance of nucleic acid structure and dynamics in the understanding of vital processes in living organisms has
developing the family of fluorescent base analogues known as the tricycliccytosines (tC) [14][29][30][31][35][36][37][38]. The aromatic core of tC was first prepared by Roth et al. in 1963 as part of a study to obtain pharmacologically active compounds structurally similar to phenothiazines [39]. Compound 1
where the acid-catalyzed cyclization as well as the glycosylation proved challenging. The latter two steps proceeded with a yield of 15% or less (17, Scheme 3).
A new synthetic approach to access substituted tricycliccytosines was envisioned in 2014 by Rodgers et al. (Scheme 4). This protocol increased
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Graphical Abstract
Figure 1:
a) Angles and unit vectors used to define the relative orientations of the donor and acceptor trans...