Department of Chemistry
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.
Jacobi PA, Adel Odeh IM, Buddhu SC, Cai G, Rajeswari S, Fry D, Zheng W, Desimone RW, Guo J, Coutts LD, Hauck SI, Leung SH, Ghosh I, Pippin D. Synthetic Studies in Phytochrome Chemistry. Synlett. 2005;19(19):2861-2885. doi: 10.1055/s-2005-918956. PMID: 18633455; PMCID: PMC2467512.
Dartmouth Digital Commons Citation
Jacobi, Peter A.; Odeh, Imad; Buddhu, Subhas; Cai, Guolin; Rajeswari, Sundaramoorthi; Fry, Douglas; Zheng, Wanjun; DeSimone, Robert W.; Guo, Jiasheng; Coutts, Lisa D.; Hauck, Sheila I.; Leung, Sam H.; Ghosh, Indranath; and Pippin, Douglas, "Synthetic Studies in Phytochrome Chemistry" (2005). Dartmouth Scholarship. 3630.