H2g

Indole-3-glycerol phosphate

Indole-3-glycerol phosphate

PLP-aminoacrylate adduct

MECHANISM FIGURE 22-18 Tryptophan synthase reaction. This enzyme catalyzes a multistep reaction with several types of chemical rearrangements. ©An aldol cleavage produces indole and glyceralde-hyde 3-phosphate; this reaction does not require PLP. ©Dehyd ration of serine forms a PLP-aminoacrylate intermediate. In steps © and @ this condenses with indole, and ©the product is hydrolyzed to release tryptophan. These PLP-facilitated transformations occur at the fi carbon (C-3) of the amino acid, as opposed to the a-carbon reactions described in Figure 18-6. The fi carbon of serine is attached to the indole ring system. ^ Tryptophan Synthase Mechanism

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