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Figure 5.
Fig. 5. Model to explain how intramolecular hydrogen
bonding in 2-hydroxyestradiol impacts negatively on its
interaction with Asn82 within the human SHBG steroid-binding
site. Ring A of 2-hydroxyestradiol and the carbamide group of
Asn82, with attached hydrogen atoms (black dots), are modeled
using the coordinates of the crystal structures of catechol (24)
and asparagine monohydrate (32), respectively. When assuming
that the hydroxyl at C-3 of 2-hydroxyestradiol forms a hydrogen
bond with the carboxylate group of Asp65, a steric clash will
occur between the hydroxyl at C-2 of the steroid ring A and the
amido group of Asn82.
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