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. Author manuscript; available in PMC: 2010 Oct 14.
Published in final edited form as: J Am Chem Soc. 2009 Oct 14;131(40):14426–14433. doi: 10.1021/ja905206k

Figure 5.

Figure 5

Reaction pathway energetics and structure for coupled chlorination of L-Thr by SyrB2 model compound. Energetics (left) of coupled mechanism show a reduced barrier of 3 kcal/mol (purple circles) compared to that of 7 kcal/mol for separate hydrogen abstraction (red diamonds) and halogenation (blue diamonds) steps. Cartoon representations (left) and tracking of key structural parameters (right) show that in coupled hydrogen abstraction (TS−H), equatorial Fe-Cl elongation stabilizes L-Thr, and in coupled chlorination (TS+Cl), hydrogen bonding from Fe-OH stabilizes L-Thr.