Table of contents

1. Matter and Measurements4h 31m
2. Atoms and the Periodic Table5h 23m
3. Ionic Compounds2h 18m
4. Molecular Compounds2h 18m
5. Classification & Balancing of Chemical Reactions3h 17m
6. Chemical Reactions & Quantities2h 27m
7. Energy, Rate and Equilibrium3h 46m
8. Gases, Liquids and Solids3h 25m
9. Solutions4h 10m
10. Acids and Bases3h 29m
11. Nuclear Chemistry56m
BONUS: Lab Techniques and Procedures1h 38m
BONUS: Mathematical Operations and Functions47m
12. Introduction to Organic Chemistry1h 34m
13. Alkenes, Alkynes, and Aromatic Compounds2h 12m
14. Compounds with Oxygen or Sulfur1h 6m
15. Aldehydes and Ketones1h 1m
16. Carboxylic Acids and Their Derivatives1h 11m
17. Amines39m
18. Amino Acids and Proteins1h 51m
19. Enzymes1h 37m
20. Carbohydrates1h 41m
21. The Generation of Biochemical Energy2h 8m
22. Carbohydrate Metabolism2h 22m
23. Lipids2h 26m
24. Lipid Metabolism1h 45m
25. Protein and Amino Acid Metabolism1h 37m
26. Nucleic Acids and Protein Synthesis2h 54m

26. Nucleic Acids and Protein Synthesis

Phosphodiester Bond Formation

GOB Chemistry

26. Nucleic Acids and Protein Synthesis

Phosphodiester Bond Formation

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Problem 74

Textbook Question

Cyclic ribose nucleotide phosphates, such as cyclic AMP (cAMP), are important signaling agents in living cells; all have the general structure shown here. What kind of linkage holds the phosphate to the ribose (see arrows; ribose is highlighted in blue)?

Verified step by step guidance

Identify the structure of the ribose sugar: Ribose is a five-carbon sugar with hydroxyl (-OH) groups attached to its carbon atoms. In this case, the ribose is cyclic, forming a furanose ring structure.

Examine the phosphate group: The phosphate group is attached to the ribose sugar through specific bonds. Look at the arrows in the image to determine which carbons of the ribose are involved in the linkage.

Determine the type of bond: The phosphate group forms ester linkages with the hydroxyl groups on the ribose. Specifically, these are phosphoester bonds, which occur when a phosphate group reacts with an -OH group, releasing water.

Analyze the cyclic nature: In cyclic AMP (cAMP), the phosphate group forms two ester linkages with two different hydroxyl groups on the ribose, creating a cyclic structure. This is known as a cyclic phosphodiester bond.

Conclude the linkage type: The linkage holding the phosphate to the ribose in cyclic AMP is a cyclic phosphodiester bond, as the phosphate is connected to two hydroxyl groups on the ribose, forming a ring structure.

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Key Concepts

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

Cyclic Nucleotide Structure

Cyclic nucleotides, like cyclic AMP (cAMP), are formed by the cyclization of ribonucleotides. This structure includes a ribose sugar, a phosphate group, and a nitrogenous base. The cyclic nature arises from a covalent bond that connects the phosphate group to the ribose, creating a ring structure that is crucial for their function as signaling molecules.

Phosphate-Ribose Linkage

The linkage between the phosphate group and the ribose in cyclic nucleotides is a phosphoester bond. This bond forms when the hydroxyl group of the ribose sugar reacts with the phosphate group, resulting in the release of a water molecule. This covalent bond is essential for the stability and functionality of cyclic nucleotides in cellular signaling.

Signaling Role of cAMP

Cyclic AMP (cAMP) serves as a secondary messenger in various signaling pathways within cells. It is produced from ATP by the enzyme adenylate cyclase and activates protein kinase A (PKA), which then phosphorylates target proteins to elicit cellular responses. Understanding the role of cAMP is vital for grasping how cells communicate and respond to external stimuli.

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