77236-72-7Relevant academic research and scientific papers
Synthese von Gallenfarbstoffen, XI. Totalsynthese und Zuordnung der relativen Konfiguration zweier epimerer Methanol-Addukte des Phycocyanobilin-dimethylesters
Gossauer, Albert,Hinze, Ralf-Peter,Kutschan, Reinhard
, p. 132 - 146 (2007/10/02)
On treatment of phycocyanobilin dimethyl ester (racem. 1) with boiling methanol, one molecule of the latter is reversibly added at the ethylidene group of the chromophore leading to the formation of only two of the four possible diastereomeric adducts.The same pigments are obtained, besides phycocyanobilin dimethyl ester, on methanolysis of the protein moiety of C-phycocyanin after esterification of the methanolic extracts.The structure and relative configurations of both methanol adducts have been elucidated by stereospecific total synthesis from the corresponding monothioimides of known relative configuration.In order to determine the latter, all four racemic stereoisomeres of 3-(1-methoxyethyl)-4-methylsuccinimide (racem. 13a - d) were synthesized, and their relative configurations - with exeption of that of racem. 13a - were determined by X-ray analysis.
