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#tautomeric shift

2 public questions tagged with this topic.

Tautomeric shift leads to

Tautomeric shift is transient isomerization where hydrogen relocates within nitrogenous base converting keto to enol or amino to imino forms, changing hydrogen-bond donor-acceptor pattern. Rare tautomer can form non-Watson-Crick pair during replication, for example enol guanine pairs with thymine instead of cytosine. If proofreading fails to excise, next replication round incorporates adenine opposite thymine, fixing single nucleotide substitution. Thus tautomerization provides classic molecular basis for spontaneous point mutations, both transitions and occasional transversions, without altering backbone. This principle illustrates essential molecular mechanisms governing replication fidelity and mutation fixation relevant for exam interpretation.

Ref: NCBI Bookshelf, Biochemistry 5th ed., Section: Tautomeric Shifts Causing Point Mutations

Tautomeric shift in guanine can cause pairing with

Purines and pyrimidines normally exist in keto-amino tautomers that form canonical Watson-Crick pairs G-C and A-T. Rare enol-imino tautomers relocate hydrogen bonding donors and acceptors altering pairing face. A transient tautomeric shift converts guanine to enol form presenting hydrogen bonding pattern similar to adenine, allowing stable pairing with thymine instead of cytosine. If uncorrected before next round of replication, replication past this mispair fixes G-C to A-T transition mutation. Phenomenon underlies spontaneous point mutations and explains mutagenesis by base analogs like bromouracil.

Ref: Watson JD et al., Molecular Biology of the Gene, 7th ed., Chapter 9: Rare tautomeric shifts and mispairing