Naphthoquinone-mediated Inhibition of Lysine Acetyltransferase KAT3B/p300 - KEY

The following questions are based on data, graphs, and figures from the following article: Naphthoquinone-mediated Inhibition of Lysine Acetyltransferase KAT3B/p300, Basis for Non-toxic Inhibitor Synthesis. Mohankrishna Dalvoy Vasudevarao et al. The Journal of Biological Chemistry, 289, 7702-7717. March 14, 2014 . doi: 10.1074/jbc.M113.486522


Fig 3A:  These data suggest a chemical reaction of NAC and DTT with plumgartin.   The generic structure of 1,4-Naphthoquinone derivatives, including plumgartin, are shown below, along with NAC and DTT. 

KAT 3A

Fig 3B; The thiol group on NAC is likely to react with a sp2 C, ultimately leading to a product which retains conjugation if possible. Draw a mechanism showing how NAC might react with the structure below, and show the final products.

KAT 3B MECH

 

KAT 3B