Beilstein J. Org. Chem.2011,7, 1504–1507, doi:10.3762/bjoc.7.175
-4CR was utilized for the synthesis of a molecular probe prototype of 1, which can be used for intercalation studies (Scheme 3). For this propose, the natural product scaffold should be attached through a spacer to a reporter tag, which is normally a luminescent group or a dye. The advanced
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Graphical Abstract
Figure 1:
Retrosynthetic scheme for (−)-julocrotine (1).
Beilstein J. Org. Chem.2010,6, No. 13, doi:10.3762/bjoc.6.13
this chromophore to DNA.
We interpret the similarity of the absorption properties together with the results from the thermal dehybridization studies, as discussed above, as a result of the intercalation of the Nile Blue dye in duplex DNA. To further explore the optical properties we recorded steady
chains and the triazolyl group represents the most critical issue for intercalation. From both molecular models it became obvious that this tether is long and flexible enough allowing the Nile Blue chromophore to intercalate in a nearly perfectly stacked position between the adjacent base pairs. This
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Graphical Abstract
Scheme 1:
Chirality of C-3 of natural 2′-deoxyribofuranosides (left) in comparison with the acyclic D-threoni...