Ch.17 Nucleic Acids and Protein Synthesis

Timberlake - Chemistry: An Introduction to General, Organic, and Biological Chemistry 13th Edition

Timberlake13th EditionChemistry: An Introduction to General, Organic, and Biological ChemistryISBN: 9780134421353Not the one you use?Change textbook

Timberlake 13th Edition

Ch.17 Nucleic Acids and Protein Synthesis

Problem 14

Chapter 17, Problem 14

A deficiency of the enzyme adenine transferase causes a lack of adenine for purine synthesis and a high level of adenine in the urine. Draw the condensed structural formula for adenosine monophosphate.

Verified step by step guidance

Understand the problem: Adenosine monophosphate (AMP) is a nucleotide composed of three main components: the nitrogenous base adenine, the sugar ribose, and a single phosphate group. The task is to draw its condensed structural formula.

Identify the structure of adenine: Adenine is a purine base with the molecular formula C₅H₅N₅. It consists of a fused double-ring system containing carbon and nitrogen atoms.

Identify the structure of ribose: Ribose is a five-carbon sugar (C₅H₁₀O₅) in its furanose (cyclic) form. In AMP, ribose is connected to adenine via a β-N-glycosidic bond at the 1' carbon of ribose and the 9th nitrogen of adenine.

Add the phosphate group: A single phosphate group (PO₄³⁻) is attached to the 5' carbon of the ribose sugar. This completes the structure of adenosine monophosphate.

Combine all components into the condensed structural formula: Write the condensed formula by combining adenine, ribose, and the phosphate group, ensuring proper connectivity. The final formula should reflect the structure of AMP, such as C₁₀H₁₄N₅O₇P.

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Key Concepts

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

Adenine and Purine Synthesis

Adenine is one of the four nucleobases in DNA and RNA, classified as a purine. Purines are essential for various biological processes, including DNA and RNA synthesis. A deficiency in adenine transferase disrupts the normal production of adenine, leading to an imbalance that affects cellular functions and results in elevated levels of adenine in urine.

Adenosine Monophosphate (AMP)

Adenosine monophosphate (AMP) is a nucleotide composed of adenine, ribose (a sugar), and a single phosphate group. It plays a crucial role in cellular energy transfer and signaling. Understanding its structure is essential for grasping how it functions in metabolic pathways and how deficiencies in related enzymes can impact its levels.

Condensed Structural Formula

A condensed structural formula is a way of representing a chemical compound that shows the arrangement of atoms and the connectivity between them without depicting all the bonds explicitly. For AMP, this formula highlights the key components—adenine, ribose, and phosphate—allowing for a clear understanding of its molecular structure and how it relates to other nucleotides.

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Condensed Formula Concept 1

Related Practice

Textbook Question

What components join together to form the backbone of a nucleic acid?

Textbook Question

What nucleic acid subunits are connected in a phosphodiester linkage in a polynucleotide?

Textbook Question

State whether each of the following components is present in DNA only, RNA only, or both DNA and RNA:

c. uracil

Textbook Question

In the genetic disease uridine monophosphate synthase deficiency, symptoms include anemia, cardiac malformations, and infections. Draw the condensed structural formula for uridine monophosphate.

Textbook Question

What component in a nucleic acid determines the 5' free end?

Textbook Question

State whether each of the following components is present in DNA only, RNA only, or both DNA and RNA:

c. deoxycytidine monophosphate