Figure 5 - full size

 

Figure 5.
FIGURE 5. Two proposed forms of the first tetrahedral intermediate (A and B) interchangeable via N-inversion and/or rotation about the C-N bond. In A, the P1' nitrogen lone pair projects away from His-57, and in B it projects toward it. In intermediate B, R and R' refer to either hydrogen or the P1' residue, depending on whether N-inversion has occurred. The amide nitrogen of Ser-195, which forms part of the oxyanion hole, is not shown for clarity; from the viewpoint shown, it lies behind the plane of the picture. Note that steric constraints mean that the conformation in which the nitrogen lone pair is exactly coplanar with the C-O(Ser-195) bond is unlikely.

The above figure is reprinted by permission from the ASBMB: J Biol Chem (2006, 281, 24024-24035) copyright 2006.