Sigma-Aldrich or Alfa Aesar and were used without further purification.
The UV light was provided by a Philips HB175 Facial Solarium (UVA,
365 nm, P = 4 × 15 W). Reverse phase column
chromatography was conducted on a Fluka Ltd. silica gel 100 C18 reversed
phase column. Analytical TLC analysis was performed using Merck 60
RP-18 F254S aluminum-supported thin layer chromatography
sheets and visualized using an ethanolic solution of ninhydrin. 1H and 13C nuclear magnetic resonance (NMR) spectra
were recorded on a Bruker Avance 400 (400 and 100 MHz) or Bruker Avance
III (500 and 125 MHz) spectrometer. Optical rotations were recorded
at 20 °C at the sodium D line (589 nm).
DNGSH was synthesized
from GSH and N-allyl-5-(dimethylamino)naphthalene-1-sulfonamide
via the photochemical thiol-ene. Glutathione-S-conjugates were synthesized
from GSH and a range of electrophiles in H2O or a H2O/methanol mixture and sodium hydroxide, via 1,4-addition.
Further details of synthesis and compound characterization are provided
in the