Biosynthesis of porphyrins and related macrocycles. Part 25. Synthesis of analogues of coproporphyrinogen-III and studies of their interaction with coproporphyrinogen-III oxidase from Euglena gracilis

Abstract

Analogues of coproporphyrinogen-III have been synthesized in which the propionate groups respectively on ring-A and on ring-B are modified either by homologation or esterification. Coproporphyrinogen-III oxidase from Euglena gracilis acts on the analogues which possess normal substituents on ring-A to generate a vinyl group on that ring. The enzyme does not affect the analogues in which the ring-A propionate group has been changed.

Conditions have been defined for the MacDonald synthesis of porphyrins which yield products of high isomeric purity.