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Methilation of the aetiobiliverdin-IV-γ-lactimether yields a lactam-N-methylated derivative the structure of which was proven by an ether cleavage and  1 H NMR spectroscopy. The configuration (Z,Z,Z) was deduced from  1 HNMR experiments. Photo-isomerization exclusively forms the (E,Z,Z) diastereomer. By conformational analysis using the LIS technique and correlations of UV-VIS spectra and PPP-type calculations a more or less helical arrangement for the two diastereomers was confirmed. The twisting is maximal at the methine single bond adjacent to the site of N-methylation, the overall geometry seems to be much more distorted than the non methylated derivatives.

zeitschrift für naturforschung b

Beiträge zur Chemie der Pyrrolpigmente, XXXIV [1]. Über die Konfiguration und Konformation von diastereomeren N-Methyl-O-methyl-bilatrienen-abc / On the Chemistry of Pyrrole Pigments, XXXIV [1] On the Configurations and Conformations of Diastereomeric N-Methyl-O-methyl-bilatrienes-abc