What is base tautomerization?

What is base tautomerization?

In DNA bases, tautomerization results in altered base pairing configurations or mispairing due to changes in hydrogen-bonding capabilities. DNA mutations are likely to be caused by such alterations. Cytosine is one of the building pyrimidine nucleobases of RNA.

What is the mechanism of tautomerism?

What is the mechanism of tautomerism? In given environments, the enol will converts into its keto form when pi electrons of the alkene abstract a hydrogen from the environment (either nearby on the compound or in the reagents), causing the lone pairs on the enol group to move down and form a carbon-oxygen double bond.

What are the types of tautomerism?

Tautomerism

• Table of Content. Tautomerism Example.
• Prototropy. It is a type of tautomerism that occurs due to the acid-base behaviour of the compound.
• Annular Tautomerism. If a proton occupies two or more position of a heterocyclic system, then such process is called annular tautomerism.
• Valence Tautomerism.

What is tautomerization with example?

Consider few examples of tautomerism given below: Page 2 Ketone-enol, enamine-imine,lactam-lactim, etc are some of the examples of tautomers. In this phenomenon, there is an exchange of a hydrogen atom between two other atoms while forming a covalent bond to either one. Tautomerism is a reversible process.

What causes tautomeric shift of bases?

The spontaneous isomerization of a nitrogen base to an alternative hydrogen-bonding form, possibly resulting in a mutation. Reversible shifts of proton position in a molecule. bases in nucleic acids shift between keto and enol forms or between amino and imino forms.

How can base tautomers lead to mutations?

(A) Spontaneous transfer of two protons from one strand to another in A-T and G-C base pairs generate minor tautomers, which can form mismatches during replication to cause mutations.

How tautomerism is different from resonance?

Tautomerism involves making and breaking of a sigma as well as pi bond. While in resonance, only the electrons in pi bonds or lone- pairs n heteroatoms shift; the sigma framework is not disturbed. This difference results in a shift of an atom from one position to another in tautomerism.

What is enol and keto?

In organic chemistry, keto–enol tautomerism refers to a chemical equilibrium between a keto form (a ketone or an aldehyde) and an enol (an alcohol). The keto and enol forms are said to be tautomers of each other.

How many forms of tautomerism are there?

There are several types of tautomerism, keto-enol tautomerism being the most important. In this type, one tautomer exists as a ketone while the other tautomer exists as an enol. Acetone and phenol are the two most common examples. Tautomerism usually happens in the presence of a catalyst.

What is another name for tautomerism?

The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the relocation of a hydrogen atom within the compound. The phenomenon of tautomerization is called tautomerism, also called desmotropism.

What is tautomeric shift in base of a DNA and what is its effect?

What is tautomeric shift in base of DNA?