Supporting Information
© Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2007
1
© Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2007
Supporting Information
for
Synthesis of 5-(1,2,3-Triazol-4-yl)-2'-deoxy-uridines by a Click Chemistry
Approach; Stacking of Triazoles in the Major Groove Gives Increased
Nucleic Acid Duplex Stability
Petr Kocalka, Nicolai K. Andersen, Frank Jensen and Poul Nielsen*
2
Figure S1
UV-spectra of compounds 3, 4 and 5 measured in aqueous solution
with 2 M sulfuric acid and 1 M NaOH for adjusting pH.
UV spectra of compound 3 at varying pH (3-12).
Absorbance of compound 3 as a function of pH values (-<-) measured at 290 nm
and the 1st derivative curve (–––).
3
UV spectra of compound 4 at varying pH (3-12).
Absorbance of compound 4 as a function of pH values (-<-) measured at 232 nm
and the 1st derivative curve (–––).
4
UV spectra of compound 5 at varying pH (3-12).
Absorbance of compound 5 as a function of pH values (-<-) measured at 290 nm
and the 1st derivative curve (–––).
5
Table S1. Changes in the dihedral angle between C-5 of the pyrimidines and C-4 of
the triazoles as obtained from molecular modeling on the duplexes in an average
over 501 measurements:
Position
from 5´end
1
complementary DNA
ON5
2
–9.1°
ON6
ON9
–12.9°
–10.3°
ON10
ON13
–9.5°
–14.2°
–5.2°
ON14
–14.2°
–15.3°
–8.8°
3
–5.7°
–0.9°
–7.1°
4
2.2°
14.1°
2.7°
Position
from 5´end
1
complementary RNA
ON5
2
–11.1°
ON6
ON9
–7.3°
–4.7°
ON10
ON13
–10.9°
–9.2°
–4.4°
ON14
–16.4°
–17.5°
–13.7°
3
–11.8°
0.6°
–6.8°
4
–5.4°
12.7°
5.8°
In general, the average changes in the dihedral angle spanned by the nucleobase
and the triazole ring indicate that the modifications are becoming more restricted in
terms of torsional rotation as the amount of π-π-stacking is increased.