Preparation and Study of Chiral Magnesium Porphyrin-Amino Acid Complexes

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Mixtures of magnesium protoporphyrin or magnesium mesoporphyrin with a variety of chiral amino acids (L-histidine, D- and L-proline, L-serine and L-threonine) produce prominent induced Cotton effects in the UV-visible region. By contrast magnesium deuteroporphyrin mixtures exhibit no optical rotatory dispersion (ORD)/circular dichroism (CD) spectra. It is proposed that the species producing the Cotton effects are six-coordinate species of the type Mg (porphyrin) (amino acid)2. For L-histidine and L-threonine CD spectra have shown that complexes of the opposite chirality can be obtained for different samples of magnesium protoporphyrin. For D- and L-proline such a change in sign of spectra was not found for the same magnesium porphyrin samples. Reasons for these observations are presented together with proposals regarding structural details of the six-coordinate complexes. It is also suggested that racemic samples of such amino acid-magnesium porphyrin mixtures could yield optical resolution of products on irradiation with circularly polarised light. Details of a study of this type are presented.

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