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Struck, A. and Cmiel, Edmund and Katheder, Ingrid and Schäfer, W. and Scheer, Hugo (1992): Bacteriochlorophylls modified at position C-3. long-range intramolecular interaction with position C-132. In: Biochimica et Biophysica Acta (BBA) - Protein Structure and Molecular Enzymology, Vol. 1101, No. 3: pp. 321-328




[3-Vinyl]-bacteriochlorophyll a and related pigments modified at C-3 and/or C-132 have been synthesized from bacteriochlorophyll a. The reactivity at C-3 is strongly influenced by the C-132 substituent, and vice versa. Spectroscopical data and comparison among derivatives modified at the isocyclic ring indicate that this interaction is related to formation of an intermediate enol(ate) structure. The possible role of enol(ate) formation in (bacterio)chlorophylls in nature is discussed.