Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

29. Amino Acids

Proteins and Amino Acids

Organic Chemistry

29. Amino Acids

Proteins and Amino Acids

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2:12 minutes

Problem 64

Textbook Question

Draw the product obtained when a lysine side chain in a polypeptide reacts with maleic anhydride.

Verified step by step guidance

Step 1: Identify the reactive groups in the lysine side chain and maleic anhydride. The lysine side chain contains a primary amine (-NH2) group, which is nucleophilic. Maleic anhydride contains an anhydride functional group, which is electrophilic and reactive towards nucleophiles.

Step 2: Understand the reaction mechanism. The primary amine group of lysine will attack one of the carbonyl carbons in the maleic anhydride through nucleophilic addition. This opens the anhydride ring, forming an amide bond and a carboxylic acid group.

Step 3: Consider the stereochemistry and connectivity. The reaction typically results in the formation of a single product where the lysine side chain is covalently bonded to the maleic anhydride derivative. Ensure the structure reflects the correct connectivity between the amine group and the maleic anhydride.

Step 4: Draw the product structure. The lysine side chain will now be attached to the maleic anhydride derivative via an amide bond. The remaining portion of the maleic anhydride will have a carboxylic acid group due to the ring opening.

Step 5: Verify the product. Ensure that the product structure is consistent with the reaction mechanism and that all atoms are accounted for. Double-check the functional groups and connectivity to confirm the accuracy of the drawn product.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Lysine Structure and Reactivity

Lysine is an amino acid with a side chain containing an amino group (-NH2) that is positively charged at physiological pH. This reactivity allows lysine to participate in nucleophilic reactions, where it can attack electrophilic centers in other molecules, such as maleic anhydride. Understanding lysine's structure is crucial for predicting its behavior in chemical reactions.

Maleic Anhydride Chemistry

Maleic anhydride is a cyclic anhydride that is highly reactive due to its electrophilic carbonyl groups. It can undergo nucleophilic addition reactions with amines, leading to the formation of stable adducts. Recognizing the reactivity of maleic anhydride is essential for understanding how it interacts with nucleophiles like the lysine side chain.

Nucleophilic Addition Reaction

Nucleophilic addition is a fundamental reaction in organic chemistry where a nucleophile attacks an electrophile, resulting in the formation of a new bond. In this case, the amino group of lysine acts as the nucleophile, attacking the electrophilic carbonyl carbon of maleic anhydride. This reaction is key to forming the product of the reaction between lysine and maleic anhydride.

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Related Practice

Textbook Question

For each compound,

1. name the functional group.

2. show what compound(s) result from complete hydrolysis.

(c)

Textbook Question

a. Calculate the overall yield of bradykinin when the yield for the addition of each amino acid to the chain is 70%.

b. What would be the overall yield of a peptide containing 15 amino acids if the yield for the incorporation of each is 80%

Textbook Question

What dipeptides would be formed by heating a mixture of valine and N-protected leucine?

Textbook Question

Proof that an imine was formed between aldolase and its substrate was obtained by using D-fructose-1,6-bisphosphate labeled at the C-2 position with ¹⁴C as the substrate. NaBH₄ was added to the reaction mixture. A radioactive product was isolated from the reaction mixture and hydrolyzed in an acidic solution. Draw the structure of the radioactive product obtained from the acidic solution. (Hint: NaBH₄ reduces an imine linkage.)

Textbook Question

Draw the tetrapeptide Ala-Thr-Asp-Asn and indicate the peptide bonds.

Multiple Choice

The unique properties of the 20 common amino acids are determined by which of the following?

Multiple Choice

How many different amino acids are commonly found in proteins?

Multiple Choice

How many standard amino acids are commonly found in proteins?

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