Synthetic Studies in Phytochrome Chemistry

摘要

An account is given of the author’s several approaches to the synthesis of the parent chromophore of phytochrome (>1), a protein-bound linear tetrapyrrole derivative that controls photomorphogenesis in higher plants. These studies culminated in enantioselective syntheses of both 2R- and 2S-phytochromobilin (>4), as well as several ¹³C-labeled derivatives designed to probe the site of Z,E-isomerization during photoexcitation. When reacted in vitro, synthetic 2R->4 and recombinant-derived phytochrome apoprotein >N-C produced a protein-bound chromophore with identical difference spectra to naturally occurring >1.