Question

Describe a tautomeric shift and how it may lead to a mutation.

Short answer

Answer: A tautomeric shift is an isomeric transformation within DNA bases that involves the migration of a hydrogen atom and the switch of a single and double bond. It can result in rare alternative forms of the DNA bases adenine, guanine, cytosine, and thymine. If this rare tautomeric form is present during DNA replication, it can lead to incorrect base pairing and potentially cause mutations if not corrected by the cell's repair mechanisms. Mutations can have various effects on the organism, ranging from neutral to harmful, depending on the specific alteration in the DNA sequence and its impact on gene function.

Step-by-step solution

Defining Tautomeric Shifts

Tautomeric shifts are isomeric transformations that involve the migration of a hydrogen atom within a molecule and the switch of a single and double bond. In the context of DNA, tautomeric shifts refer to rare alternative forms of the DNA bases adenine, guanine, cytosine, and thymine. These alternative forms can lead to incorrect base pairing during DNA replication, potentially causing mutations.

Types of Tautomeric Shifts

There are two main types of tautomeric shifts: keto-enol and amino-imino. Keto-enol tautomeric shifts involve the movement of a hydrogen atom between the carbonyl (keto) and hydroxyl (enol) groups. In terms of DNA, this shift occurs in adenine and thymine. Amino-imino tautomeric shifts involve the movement of a hydrogen atom between the amino and imino groups and occur in cytosine and guanine. In both cases, the shift results in a rare tautomeric form of the DNA base.

Effects of Tautomeric Shifts

When a rare tautomeric form is present during DNA replication, it can lead to incorrect base pairing. For example, a keto-enol shift in adenine could cause it to pair with cytosine, while a keto-enol shift in thymine could cause it to pair with guanine. Similarly, an amino-imino shift in guanine could cause it to pair with thymine, and an amino-imino shift in cytosine could cause it to pair with adenine. The mispairing of bases may lead to a permanent mutation if not corrected by DNA repair mechanisms.

Tautomeric Shifts and Mutations

Tautomeric shifts can lead to mutations if the altered base pairing persists and is not corrected by the cell. The replication of DNA with a rare tautomeric form present can result in a permanent base pair change, altering the genetic information encoded within the DNA. These mutations can cause various effects, ranging from neutral or harmless to potentially harmful or lethal, depending on the specific alteration in the DNA sequence and its impact on gene function. In summary, a tautomeric shift is an isomeric transformation within DNA bases that can lead to incorrect base pairings during DNA replication. If these incorrect pairings are not corrected, they can result in permanent mutations with various consequences for the organism and its future generations.