Assign an \(R\) or \(S\) configuration to the chiral center in each amino acid. (a) L-Phenylalanine (b) L-Glutamic acid (c) L-Methionine

Short Answer

Expert verified
Answer: The chiral center configurations for each amino acid are L-Phenylalanine (S), L-Glutamic acid (S), and L-Methionine (S).

Step by step solution

01

Determine the chiral centers

In each amino acid, the chiral center is the α-carbon, which is the carbon atom attached to the amino group (NH2), carboxyl group (COOH), and the side chain (R group).
02

Assign priorities to the groups around the chiral center

Using the Cahn-Ingold-Prelog priority rules, assign priorities to the groups attached to the chiral center. Number the atoms in decreasing order of priority (1 for the highest priority, 4 for the lowest priority). The priority is usually determined by atomic number, with higher atomic numbers having higher priority.
03

Arrange the lowest priority group away from the observer

Position the molecule in space so that the lowest-priority group (4) is pointing away from the observer.
04

Determine the orientation of the three remaining groups

Observe the orientation of the remaining three groups around the chiral center. If the order of priority from 1 to 3 is clockwise, the configuration is R (rectus). If the order of priority from 1 to 3 is counterclockwise, the configuration is S (sinister).
05

Assign configuration to each amino acid

(a) L-Phenylalanine: 1. Chiral center: α-carbon 2. Priorities: COOH (1) > NH2 (2) > Phenyl group (3) > H (4) 3. Arrange H away from the observer 4. Orientation: counterclockwise (sinister) Configuration: S (b) L-Glutamic acid: 1. Chiral center: α-carbon 2. Priorities: COOH (1) > NH2 (2) > CH2-COOH (3) > H (4) 3. Arrange H away from the observer 4. Orientation: counterclockwise (sinister) Configuration: S (c) L-Methionine: 1. Chiral center: α-carbon 2. Priorities: COOH (1) > NH2 (2) > CH2-CH2-S-CH3 (3) > H (4) 3. Arrange H away from the observer 4. Orientation: counterclockwise (sinister) Configuration: S In conclusion, the chiral center configurations for each amino acid are L-Phenylalanine (S), L-Glutamic acid (S), and L-Methionine (S).

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