Chorismate mutase is an enzyme that promotes a pericyclic reaction by forcing the substrate to assume the conformation needed for the reaction. The product of the pericyclic reaction is prephenate that is subsequently converted into the amino acids phenylalanine and tyrosine. What kind of a pericyclic reaction does chorismate mutase catalyze?
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Verified step by step guidance

1. Identify the substrate involved in the reaction catalyzed by chorismate mutase, which is chorismate.
2. Understand that chorismate mutase catalyzes a pericyclic reaction, which involves a concerted process where bonds are formed and broken in a cyclic transition state.
3. Recognize that the reaction type is a [3,3]-sigmatropic rearrangement, specifically known as the Claisen rearrangement, which is a common pericyclic reaction.
4. Note that in this rearrangement, a six-membered cyclic transition state is formed, leading to the conversion of chorismate to prephenate.
5. Acknowledge that this reaction is crucial in the biosynthesis pathway of aromatic amino acids, such as phenylalanine and tyrosine.

Key Concepts

Pericyclic Reactions

Pericyclic reactions are a class of organic reactions that occur through a concerted mechanism, involving the cyclic rearrangement of electrons. These reactions typically involve the simultaneous breaking and forming of bonds in a cyclic transition state, which can lead to various products. Common types include cycloadditions, electrocyclic reactions, and sigmatropic rearrangements, each characterized by specific electron movement and stereochemical outcomes.

Chorismate Mutase Function

Chorismate mutase is an enzyme that catalyzes the conversion of chorismate to prephenate, a key step in the biosynthesis of aromatic amino acids. This enzyme facilitates a pericyclic rearrangement, specifically a Claisen rearrangement, which involves the migration of a substituent within the molecule. Understanding its mechanism is crucial for grasping how it influences the production of phenylalanine and tyrosine.

Aromatic Amino Acid Biosynthesis

Aromatic amino acid biosynthesis refers to the metabolic pathways that produce essential amino acids like phenylalanine and tyrosine from simpler precursors. These amino acids are vital for protein synthesis and serve as precursors for various biomolecules. The conversion of prephenate to these amino acids involves additional enzymatic steps, highlighting the interconnectedness of metabolic pathways in living organisms.