Total Syntheses of Sterically Locked Phycocyanobilin Derivatives Bearing a 15Z-anti or a 15E-anti CD-Ring Component

Total syntheses of sterically locked phycocyanobilin derivatives with a 15Z-anti or a 15E-anti CD-ring component were performed toward elucidation of the stereochemistry and function of the chromophore in phytochromes. In the course of the construction of a sterically locked 15E-anti CD-ring compone...

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Published inBulletin of the Chemical Society of Japan Vol. 83; no. 11; pp. 1309 - 1322
Main Authors Nishiyama, Kaori, Kamiya, Ayumi, Hammam, Mostafa A. S, Kinoshita, Hideki, Fujinami, Shuhei, Ukaji, Yutaka, Inomata, Katsuhiko
Format Journal Article
LanguageEnglish
Published TOKYO The Chemical Society of Japan 2010
Chemical Soc Japan
Chemical Society of Japan
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
BILIVERDIN DERIVATIVES
RED-ABSORBING FORM
PSEUDOMONAS-AERUGINOSA BACTERIOPHYTOCHROME
CHROMOPHORE
CRYSTAL-STRUCTURE
LIGHT
PHOTOCONVERSION
AGROBACTERIUM PHYTOCHROMES AGP1
A,B-RINGS COMPONENT
PFR
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Summary:Total syntheses of sterically locked phycocyanobilin derivatives with a 15Z-anti or a 15E-anti CD-ring component were performed toward elucidation of the stereochemistry and function of the chromophore in phytochromes. In the course of the construction of a sterically locked 15E-anti CD-ring component employing 5-tosylpyrrolin-2-one derivatives as the D-ring, the Ts group was found to be rearranged under acidic conditions to give a mixture of regioisomers, both of which could be transformed into the same CD-ring precursor via detosylation with a base followed by Wittig-like coupling reaction. In addition, a sterically locked 15E-anti biliverdin derivative was also synthesized.
Bibliography:KAKEN
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.20100168