Synthesis of Selectively ¹³C‐Labelled Bilin Compounds

Abstract

A series of open-chain tetrapyrroles, each carrying one or more 13 C-labels in its three ring-bridging methine groups, were synthesized. These compounds - [5-, [10-, and [15-13 C]-phycocyanobilins (PCB), [10-13 C]-phytochromobilin, and [10,15-13 C 2 ]-PCB -were each obtained by a convergent route, starting with the four pyrrole building blocks, with the initial formation of the left and the right halves of the tetrapyrrole separately, followed by a final condensation of the two dipyrrole units to yield the target bilin compound. The

Pd‐Catalyzed Threefold Arylation of Baylis–Hillman Bromides and Acetates with Triarylbismuth Reagents

“…Ethyl and n ‐butyl derivatives of 2‐bromomethylacrylates that were required for this study were synthesized by using literature procedures 4. The corresponding benzyl derivative was also prepared by literature methods 12a,12b. Alkyl 2‐(acetoxymethyl)acrylates and 2‐(acetoxymethyl)acrylonitriles were also obtained by using known methods 12c.…”

Chromophore Structure of Cyanobacterial Phytochrome Cph1 in the Pr State: Reconciling Structural and Spectroscopic Data by QM/MM Calculations

“…The synthesis of 13 C(5)-labeled PCB has been described elsewhere (38). Unlabeled PCB was obtained by methanolysis of freeze-dried Spirulina in analogy to the procedure described by Strauss et al (39) and purified by preparative reverse-phase high-performance liquid chromatography.…”

The Chromophore Structures of the Pr States in Plant and Bacterial Phytochromes

“…15-D-PCB was synthesized as described by Knipp et al (13). 5-13 C-PCB was synthesized according to Makhynya et al (14). The synthesis followed the convergent strategy by generating the right and the left half of PCB separately ( Fig.…”