Table S7. Proton chemical shifts () and coupling constants (J) for the decomposition products arising from heating or UV-irradiation
of the cyclobutane dimers of 5-bromo-2’-deoxyuridine.
Product
VIIc
PB6d1
PB6d2†
H6
8.11 (s)
8.27 (s)
8.84 (s,1.0)
H1’
6.33 (t)
6.32 (t)
6.44 (t,1.1)
H2’
H2”
2.39
2.46
2.41
2.49
2.35 (1.9) 2.67 (1.6)
H3’
4.47
4.48
4.47 (1.0)
H4’
4.06
4.08
4.20 (0.5)
H5’
3.83
3.85
3.94(1.0)
H5”
3.76
3.77
3.84 (1.4)
Product
H1'-H2'
H1'-H2''
H2'-H2''
H2'-H3'
H2''-H3'
H3'-H4'
H4'-H5'
H4'-H5''
6.5
6.4
14.3
6.5
4.4
3.8
3.0
4.9
VIIc
PB6d1
6.2
5.9
14.0
6.3
5.6
4.4
3.1
4.5
PB6d2
6.0
6.0
14.0
6.3
5.3
4.0
3.0
5.0
Proton NMR spectra were run in D2O, using TSP as a reference compound. The chemical shifts in ppm () (upper table) and
H5'-H5''
12.6
12.5
12.4
magnitudes of the coupling constants in Hz (J) (lower table) for the sugar protons were estimated with SpinWorks (Version 3.1, 2009,
Kirt Marat, University of Minnesota), using the simulation module, NUMMRIT, with default parameters. (NUMMRIT algorithm
reference: J. S. Martin and A. R. Quirt, J. Magn. Reson. 5, 318 (1971)). For each product, the simulated proton NMR spectrum
provided a reasonable match for the experimental spectrum. †While the integrated areas for the various protons in VIIc and PB6d1 are
in reasonable agreement with the expected values for compounds with two and one deoxyribose rings respectively, interpretation of
the corresponding values for PB6d2 is not straightforward. These integrated areas, rounded to one decimal place and normalized to H6
as unity, are given in parentheses. However, these values for PB6d2 may be artefactual, resulting from dealing with a baseline of less
than ideal quality.