1. Below is the structure of N-a-acetyl-lysine. LHO H2N 'N' H unotos TEE MHD N-alpha-acetyl-lysine Label the chiral center(s) in the N-a-acetyl-lysine with *. b. Draw the molecule in its most common protonation state at pH 7. a. HO H2N NH2 TCI lysine acetyl chloride C. The molecule can be made from reaction of lysine with acetyl chloride (see structures above). Draw the reaction mechanism, including any relevant intermediate, using the arrow formalism.

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### Problem 1: Structure and Reaction of N-α-acetyl-lysine

**1. Below is the structure of N-α-acetyl-lysine.**

![N-alpha-acetyl-lysine structure](image-link-placeholder)

**Structure:**
- The structure depicted is N-alpha-acetyl-lysine. It consists of a lysine backbone with an acetyl group attached to the alpha-nitrogen.

**Tasks:**

**a. Label the chiral center(s) in the N-α-acetyl-lysine with *.**

- Identify the carbon atom in the molecule that has four different groups attached to it, which makes it a chiral center, and label it with an asterisk (*).

**b. Draw the molecule in its most common protonation state at pH 7.**

- At pH 7, identify the protonation state of N-alpha-acetyl-lysine, considering the ionizable groups typically found in amino acids and their derivatives (e.g., amino, carboxyl, and side chain groups).

**c. The molecule can be made from the reaction of lysine with acetyl chloride (see structures above). Draw the reaction mechanism, including any relevant intermediate, using the arrow formalism.**

**Structures:**
- Lysine: Contains an amino group, a carboxyl group, and a side chain.
- Acetyl chloride: Contains an acetyl group connected to chlorine.

- Illustrate the step-by-step reaction pathway, using arrows to show the movement of electrons during the formation of N-alpha-acetyl-lysine from lysine and acetyl chloride.

**d. What's the name of the new functional group that is formed in (c)?**

- Identify the new functional group produced during the reaction between lysine and acetyl chloride (e.g., amide bond).

**e. Imagine that you carry out the reaction under the following conditions: neutral pH, acetonitrile, 10 mM lysine, 10 mM acetyl chloride. The reaction will yield one other (i.e., additional) major organic product. Draw this organic product.**

- Consider possible additional reactions or side products that can form under these conditions, and draw the structure of the major product.

**f. Now imagine that you carry out the reaction under the following conditions: neutral pH, acetonitrile, 10 mM lysine
Transcribed Image Text:### Problem 1: Structure and Reaction of N-α-acetyl-lysine **1. Below is the structure of N-α-acetyl-lysine.** ![N-alpha-acetyl-lysine structure](image-link-placeholder) **Structure:** - The structure depicted is N-alpha-acetyl-lysine. It consists of a lysine backbone with an acetyl group attached to the alpha-nitrogen. **Tasks:** **a. Label the chiral center(s) in the N-α-acetyl-lysine with *.** - Identify the carbon atom in the molecule that has four different groups attached to it, which makes it a chiral center, and label it with an asterisk (*). **b. Draw the molecule in its most common protonation state at pH 7.** - At pH 7, identify the protonation state of N-alpha-acetyl-lysine, considering the ionizable groups typically found in amino acids and their derivatives (e.g., amino, carboxyl, and side chain groups). **c. The molecule can be made from the reaction of lysine with acetyl chloride (see structures above). Draw the reaction mechanism, including any relevant intermediate, using the arrow formalism.** **Structures:** - Lysine: Contains an amino group, a carboxyl group, and a side chain. - Acetyl chloride: Contains an acetyl group connected to chlorine. - Illustrate the step-by-step reaction pathway, using arrows to show the movement of electrons during the formation of N-alpha-acetyl-lysine from lysine and acetyl chloride. **d. What's the name of the new functional group that is formed in (c)?** - Identify the new functional group produced during the reaction between lysine and acetyl chloride (e.g., amide bond). **e. Imagine that you carry out the reaction under the following conditions: neutral pH, acetonitrile, 10 mM lysine, 10 mM acetyl chloride. The reaction will yield one other (i.e., additional) major organic product. Draw this organic product.** - Consider possible additional reactions or side products that can form under these conditions, and draw the structure of the major product. **f. Now imagine that you carry out the reaction under the following conditions: neutral pH, acetonitrile, 10 mM lysine
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