Synthesis of Sterically Fixed Phytochrome Chromophore Derivatives Bearing a 15E-Fixed or 15E-Anti-Fixed CD-Ring Component

Synthesis of Sterically Fixed Phytochrome Chromophore Derivatives Bearing a 15E-Fixed or 15E-Anti-Fixed CD-Ring Component

To analyze the structure and function of phytochrome chromophores, we have been synthesizing natural and unnatural bilin chromophores of phytochromes. In this manuscript, we report the synthesis of sterically fixed 15E-fixed 18Et-biliverdin (BV) and 15E-anti-fixed 18Et-BV derivatives. The key reacti...

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Veröffentlicht in:Journal of organic chemistry 2018-09, Vol.83 (18), p.10743-10748
Hauptverfasser: Soeta, Takahiro, Ohashi, Nobuhiko, Kobayashi, Toshiharu, Sakata, Yoko, Suga, Takuya, Ukaji, Yutaka
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container_end_page 10748
container_issue 18
container_start_page 10743
container_title Journal of organic chemistry
container_volume 83
creator Soeta, Takahiro
Ohashi, Nobuhiko
Kobayashi, Toshiharu
Sakata, Yoko
Suga, Takuya
Ukaji, Yutaka
description To analyze the structure and function of phytochrome chromophores, we have been synthesizing natural and unnatural bilin chromophores of phytochromes. In this manuscript, we report the synthesis of sterically fixed 15E-fixed 18Et-biliverdin (BV) and 15E-anti-fixed 18Et-BV derivatives. The key reaction is the introduction of an sp3 carbon alkyl chain bearing a leaving group at the meso-position of the CD-ring component by using the corresponding Grignard reagents in the presence of LiCl.
doi_str_mv 10.1021/acs.joc.8b01252
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title Synthesis of Sterically Fixed Phytochrome Chromophore Derivatives Bearing a 15E-Fixed or 15E-Anti-Fixed CD-Ring Component
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