Figure 1.
HPLC-UV chromatograms of DNA and the mechlorethamine-crosslinked DNA duplex.
A: Top-strand DNA. B: Bottom-strand DNA. C: DNA duplex (denatured on the column). D: The mechlorethamine-crosslinked DNA duplex.
Figure 2.
MALDI-TOF-MS spectrum of the mechlorethamine-crosslinked DNA duplex.
Figure 3.
HPLC-UV chromatograms of monodeoxynucleosides.
A: SVPD and CIP-digested poly-dC, poly-dG, poly-dT and poly-dA. B: Standard dC, dG, dT and dA. C: SVPD- and CIP-digested products of top-strand DNA. D: SVPD- and CIP-digested products of bottom-strand DNA. E: SVPD- and CIP-digested products of DNA duplex. F: SVPD- and CIP-digested products of the mechlorethamine-crosslinked DNA duplex.
Figure 4.
Structures of possible mechlorethamine crosslinks at a cytosine-cytosine mismatch pair.
A: A mechlorethamine crosslink through O2 of cytosine. B: A mechlorethamine crosslink through N3 of cytosine. C: A mechlorethamine crosslink through N4 of cytosine. Note that the O2 and N4 crosslinks are neutral species that form with loss of 2H+ from the nucleosides, whereas the N3 crosslink has a double positive charge.
Figure 5.
ESI-MS/MS analysis of N3dC-mech-N3dC.
A: ESI-MS/MS spectrum of N3dC-mech-N3dC. B: Fragmentation pattern of N3dC-mech-N3dC. The IUPAC name for N3dC-mech-N3dC is [4-amino-3-[2-[2-[6-amino-3-[4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-2-oxo-pyrimidin-1-ium-1-yl]ethyl-methyl-amino]ethyl]-1-[4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-3-ium-2-one].
Figure 6.
ESI-MS/MS analysis of N3dC-mech-OH.
A: ESI-MS/MS spectrum of N3dC-mech-OH. B: Fragmentation pattern of N3dC-mech-OH. The IUPAC name for N3dC-mech-OH is [4-amino-3-[2-(2-hydroxyethyl(methyl)amino)ethyl]-1-[4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-3-ium-2-one].