Synthetic Studies in Phytochrome Chemistry

Authors

Peter A. Jacobi, Dartmouth College
Imad Odeh, Dartmouth College
Subhas Buddhu, Dartmouth College
Guolin Cai, Dartmouth CollegeFollow
Sundaramoorthi Rajeswari, Dartmouth College
Douglas Fry, Dartmouth College
Wanjun Zheng, Dartmouth College
Robert W. DeSimone, Dartmouth College
Jiasheng Guo, Dartmouth College
Lisa D. Coutts, Dartmouth College
Sheila I. Hauck, Dartmouth College
Sam H. Leung, Dartmouth College
Indranath Ghosh, Dartmouth College
Douglas Pippin, Dartmouth College

Document Type

Article

Publication Date

2005

Publication Title

Synlett

Department

Department of Chemistry

Abstract

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.

DOI

10.1055/s-2005-918956

Original Citation

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.
https://digitalcommons.dartmouth.edu/facoa/3630