Effect of Vitamin D Conformation on Interactions and Packing in the Crystal Lattice,Crystal Growth & Design

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Effect of Vitamin D Conformation on Interactions and Packing in the Crystal Lattice
Crystal Growth & Design ( IF 3.2 ) Pub Date : 2018-04-19 00:00:00 , DOI: 10.1021/acs.cgd.8b00091
Monika Wanat _{1,

2} , Maura Malinska ₁ , Andrzej Kutner ₃ , Krzysztof Wozniak ₁

Affiliation

The crystal and molecular structures of a series of structurally related analogues of 1,25-dihydroxyvitamin D₂ 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.

中文翻译：

维生素D构象对晶格相互作用和堆积的影响

1,25-二羟基维生素D ₂的一系列与结构相关的类似物的晶体和分子结构通过单晶X射线结构分析确定了具有所有羟基被保护的第一个类似物。利用新的结构数据，我们提出了A环的构型取决于A环的羟基的氢键。1α-羟基化维生素D类似物的A环以固态存在于优选的椅子β构象中，该构象是由1-OH和3-OH羟基之间的直接氢键引起的。在相同的A环构象中，维生素D类似物与维生素D受体相互作用。A环羟基之间的间接氢键（例如通过水分子的氢键）或A环羟基和侧链羟基之间的氢键可诱导α构象。在真空中进行的理论计算表明，β-形式的能量略低于α-形式。不仅羟基而且环外亚甲基也极大地影响分子间的相互作用，包括晶格中的氢键模式。

更新日期：2018-04-19

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