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. Author manuscript; available in PMC: 2018 Oct 11.
Published in final edited form as: Org Biomol Chem. 2017 Oct 11;15(39):8341–8353. doi: 10.1039/c7ob02096a

Scheme 4.

Scheme 4

Attack trajectory of H2O on oxidized dOG determines the stereochemistry of dSp. (A) The re vs. si faces of dOG when base paired with dC in a duplex. (B) Attack trajectory of H2O on oxidized dOG determines the stereochemistry of the intermediate 5-HO-dOG that undergoes stereospecific 1,2-acyl shift to dSp.