ArticleBiochemistry2010
Biliverdin amides reveal roles for propionate side chains in bilin reductase recognition and in holophytochrome assembly and photoconversion.
Article in Biochemistry, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 34 citations in OpenAlex.
- Circular dichroism spectroscopy reveals multiple phytochrome photoproducts in equilibrium.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2025Article
- Conserved histidine and tyrosine determine spectral responses through the water network in Deinococcus radiodurans phytochrome.Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology · 2022Article
- Pressurized Liquid Extraction of a Phycocyanobilin Chromophore and Its Reconstitution with a Cyanobacteriochrome Photosensor for Efficient Isotopic Labeling.Plant & cell physiology · 2021Article
- Spectral and photochemical diversity of tandem cysteine cyanobacterial phytochromes.The Journal of biological chemistry · 2020Article
- Article
- The phycocyanobilin chromophore of streptophyte algal phytochromes is synthesized by HY2.The New phytologist · 2017Article
- A substrate-bound structure of cyanobacterial biliverdin reductase identifies stacked substrates as critical for activity.Nature communications · 2017Article
- Structure of the cyanobacterial phytochrome 2 photosensor implies a tryptophan switch for phytochrome signaling.The Journal of biological chemistry · 2013Article
- Genomic analysis reveals key aspects of prokaryotic symbiosis in the phototrophic consortium "Chlorochromatium aggregatum".Genome biology · 2013Article
- Green/red cyanobacteriochromes regulate complementary chromatic acclimation via a protochromic photocycle.Proceedings of the National Academy of Sciences of the United States of America · 2013Article
- Diverse two-cysteine photocycles in phytochromes and cyanobacteriochromes.Proceedings of the National Academy of Sciences of the United States of America · 2011Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Linear tetrapyrroles (bilins) perform important antioxidant and light-harvesting functions in cells from bacteria to humans. To explore the role of the propionate moieties in bilin metabolism, we report the semisynthesis of mono- and diamides of biliverdin IXalpha and those of its non-natural XIIIalpha isomer. Initially, these were examined as substrates of two types of NADPH-dependent biliverdin reductase, BVR and BvdR, and of the representative ferredoxin-dependent bilin reductase, phycocyanobilin:ferredoxin oxidoreductase (PcyA). Our studies indicate that the NADPH-dependent biliverdin reductases are less accommodating to amidation of the propionic acid side chains of biliverdin IXalpha than PcyA, which does not require free carboxylic acid side chains to yield its phytobilin product, phycocyanobilin. Bilin amides were also assembled with BV-type and phytobilin-type apophytochromes, demonstrating a role for the 8-propionate in the formation of the spectroscopically native P(r) dark states of these biliprotein photosensors. Neither ionizable propionate side chain proved to be essential to primary photoisomerization for both classes of phytochromes, but an unsubstituted 12-propionate was required for full photointerconversion of phytobilin-type phytochrome Cph1. Taken together, these studies provide insight into the roles of the ionizable propionate side chains in substrate discrimination by two bilin reductase families while further underscoring the mechanistic differences between the photoconversions of BV-type and phytobilin-type phytochromes.
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