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

21. Aldehydes and Ketones: Nucleophilic Addition

Imine vs Enamine

Organic Chemistry

21. Aldehydes and Ketones: Nucleophilic Addition

Imine vs Enamine

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2:29 minutes

Problem 72

Textbook Question

The nucleosides that make up DNA have heterocyclic rings linked to deoxyribose by an aminoacetal functional group. Point out the aminoacetal linkages in deoxycytidine and deoxyadenosine.

Verified step by step guidance

Step 1: Understand the structure of nucleosides. Nucleosides consist of a nitrogenous base (heterocyclic ring) linked to a sugar molecule (deoxyribose in DNA) via a glycosidic bond. In this case, the bond is an aminoacetal linkage.

Step 2: Identify the nitrogenous bases in deoxycytidine and deoxyadenosine. Deoxycytidine contains cytosine as its base, while deoxyadenosine contains adenine as its base. These bases are heterocyclic rings.

Step 3: Locate the deoxyribose sugar in the structures. The sugar is a five-membered ring with hydroxyl groups and a hydrogen atom replacing the hydroxyl group at the 2' position, characteristic of deoxyribose.

Step 4: Examine the bond between the nitrogenous base and the sugar. The aminoacetal linkage is formed between the nitrogen atom of the base and the anomeric carbon of the sugar. This bond is a glycosidic bond, specifically an N-glycosidic bond.

Step 5: In the provided structures, identify the aminoacetal linkage. For deoxyadenosine, the bond between the nitrogen atom in adenine and the anomeric carbon of deoxyribose is the aminoacetal linkage. Similarly, for deoxycytidine, the bond between the nitrogen atom in cytosine and the anomeric carbon of deoxyribose is the aminoacetal linkage.

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Key Concepts

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

Nucleosides

Nucleosides are organic molecules composed of a nitrogenous base linked to a sugar molecule, specifically ribose or deoxyribose. In DNA, nucleosides consist of a deoxyribose sugar attached to one of four nitrogenous bases: adenine, cytosine, guanine, or thymine. Understanding the structure of nucleosides is crucial for recognizing how they form the building blocks of DNA.

Aminoacetal Functional Group

An aminoacetal functional group is formed when an amine group is attached to a carbon atom that is also bonded to an ether or acetal group. In the context of nucleosides, this linkage connects the nitrogenous base to the sugar, facilitating the formation of nucleotides. Identifying this linkage is essential for understanding the structural integrity and function of nucleic acids.

Chemical Structure of Deoxycytidine and Deoxyadenosine

Deoxycytidine and deoxyadenosine are specific nucleosides that contain the nitrogenous bases cytosine and adenine, respectively, linked to deoxyribose. Analyzing their chemical structures reveals the aminoacetal linkages that connect the bases to the sugar. Recognizing these structures is vital for understanding how nucleosides contribute to the overall architecture of DNA.

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