Two adjacent thymidine residues in DNA can dimerize in the presence of UV light to form thymine dimers. The reaction occurs via a [2+2] cycloaddition reaction. Thymine dimers can be repaired by DNA repair enzymes. However, DNA repair enzymes occasionally make mistakes which lead to mutations and eventually skin cancer. There are two [2+2] cycloaddition reactions that can occur between two thymidine residues. detailed mechanisms for both. (HINT: One of them has a heterocyclic ring intermediate.) Draw Me HN N. R Figure 1: thymidine residue. R - sugar phosphate backbone of DNA

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Two adjacent thymidine residues in DNA can dimerize in the presence of UV light to form thymine dimers.
The reaction occurs via a [2+2] cycloaddition reaction. Thymine dimers can be repaired by DNA repair
enzymes. However, DNA repair enzymes occasionally make mistakes which lead to mutations and eventually
skin cancer.
There are two [2+2] cycloaddition reactions that can occur between two thymidine residues. Draw
detailed mechanisms for both. (HINT: One of them has a heterocyclic ring intermediate.)
Me
HN
N.
R
Figure 1: thymidine residue. R - sugar phosphate backbone of DNA
Transcribed Image Text:Two adjacent thymidine residues in DNA can dimerize in the presence of UV light to form thymine dimers. The reaction occurs via a [2+2] cycloaddition reaction. Thymine dimers can be repaired by DNA repair enzymes. However, DNA repair enzymes occasionally make mistakes which lead to mutations and eventually skin cancer. There are two [2+2] cycloaddition reactions that can occur between two thymidine residues. Draw detailed mechanisms for both. (HINT: One of them has a heterocyclic ring intermediate.) Me HN N. R Figure 1: thymidine residue. R - sugar phosphate backbone of DNA
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