Inverted Binding of Non-natural Substrates in Strictosidine Synthase Leads to a Switch of Stereochemical Outcome in Enzyme-Catalyzed Pictet-Spengler Reactions.

The data in Figure 6 C show a clear trend in which ( R )- int-II often achieves a conformation close to the transition structure, or an optimal near-attack-conformation, whereas ( S )- int-II has a poor geometry for deprotonation despite being proximal to the catalytic residue.

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