Single chirality through crystal grinding
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RU Radboud Universiteit Nijmegen, 13 januari 2010
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Solid State Chemistry
SubjectSolid State Chemistry
The properties of chiral molecules in living organisms can be different for left- and right-handed molecules. Therefore, ways to produce molecules of single handedness are of paramount importance, especially for economical, high yielding processes to synthesize pharmaceutical compounds that must be registered in one form. This thesis describes a novel method to transform a mixture of left- and right-handed molecules into one desired handedness. Simply by grinding a mixture of left- and right-handed crystals of these molecules in contact with a solution, in which the left- and right-handed molecules can be converted into each other, the solid phase evolves to single handedness. Having proven this principle, we moved on to demonstrate the general applicability by applying this grinding method to a variety of molecules including amino acids and a pharmaceutical compound. Additionally, we discovered a gamut of ways to steer the end state either to left or right handedness. For instance, the rotation sense of circularly polarized light could be used to dictate the outcome. Compared to asymmetric synthesis and separation of enantiomers, this grinding method is a promising route to make pharmaceutical compounds of single handedness. From another perspective, the results presented in this thesis outline a possible pathway to the single handedness found in nature, thereby contributing to the discussion on the emergence of prebiotic molecules that formed the building blocks of life.
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