Effect of Vitamin D Conformation on Interactions and
Packing in the Crystal Lattice
Monika Wanat
Maura Malinska
Andrzej Kutner
Krzysztof Wozniak
10.1021/acs.cgd.8b00091.s001
https://acs.figshare.com/articles/journal_contribution/Effect_of_Vitamin_D_Conformation_on_Interactions_and_Packing_in_the_Crystal_Lattice/6205799
The
crystal and molecular structures of a series of structurally
related analogues of 1,25-dihydroxyvitamin D<sub>2</sub> and of the
first analogue with all hydroxyl groups protected were established
with single crystal X-ray structural analysis. With the use of the
new structural data, we proposed that the A-ring conformation depends
on hydrogen bonding of the hydroxyl groups of the A-ring. The A-ring
of the 1α-hydroxylated vitamin D analogues exists in the solid
state in a preferred chair β-conformation induced by direct
hydrogen bonds between the 1-OH and 3-OH hydroxyl groups. In the same
A-ring conformation, the vitamin D analogue interacts with the vitamin
D receptor. Indirect hydrogen bonds between the A-ring hydroxyl groups,
such as the ones through the water molecule, or hydrogen bonds between
the A-ring hydroxyl groups and side-chain hydroxyl groups, induce
the α-conformation. Theoretical calculations performed in vacuo
showed that the β-form has a slightly lower energy than the
α-form. Not only the hydroxyl groups but also the exocyclic
methylene highly influences intermolecular interactions including
the hydrogen bond pattern in the crystal lattices.
2018-04-19 00:00:00
vitamin D analogue
A-ring conformation
Indirect hydrogen bonds
Vitamin D Conformation
hydrogen bonds
side-chain hydroxyl groups
vitamin D receptor
3- OH hydroxyl groups
A-ring hydroxyl groups
hydrogen bond pattern
hydroxyl groups
chair β- conformation
1α- hydroxylated vitamin D analogues
crystal