ArticleScientific reports2014
In vitro conversion of vinyl to formyl groups in naturally occurring chlorophylls.
Article in Scientific reports, 2014. 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, 35 citations in OpenAlex.
- Article
- An Update on the Use of Natural Pigments and Pigment Nanoparticle Adducts for Metal Detection Based on Colour Response.Biosensors · 2023Review
- Rieske Oxygenase Catalyzed C-H Bond Functionalization Reactions in ChlorophyllACS central science · 2022Article
- Far-red light allophycocyanin subunits play a role in chlorophyll d accumulation in far-red light.Photosynthesis research · 2020Article
- Characterization of chlorophyll f synthase heterologously produced in Synechococcus sp. PCC 7002.Photosynthesis research · 2019Article
- Spectral signatures of five hydroxymethyl chlorophyll a derivatives chemically derived from chlorophyll b or chlorophyll f.Photosynthesis research · 2019Article
- Global Transcriptional Profiling of the CyanobacteriumFrontiers in microbiology · 2019Article
- The C2The Journal of biological chemistry · 2017Article
- Photosynthesis at the far-red region of the spectrum in Acaryochloris marina.Biological research · 2017Review
- The Complex Transcriptional Response ofG3 (Bethesda, Md.) · 2017Article
- Two Unrelated 8-Vinyl Reductases Ensure Production of Mature Chlorophylls in Acaryochloris marina.Journal of bacteriology · 2016Article
Corrections and comments
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Authors and funding
3 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The chemical structural differences distinguishing chlorophylls in oxygenic photosynthetic organisms are either formyl substitution (chlorophyll b, d, and f) or the degree of unsaturation (8-vinyl chlorophyll a and b) of a side chain of the macrocycle compared with chlorophyll a. We conducted an investigation of the conversion of vinyl to formyl groups among naturally occurring chlorophylls. We demonstrated the in vitro oxidative cleavage of vinyl side groups to yield formyl groups through the aid of a thiol-containing compound in aqueous reaction mixture at room temperature. Heme is required as a catalyst in aqueous solution but is not required in methanolic reaction mixture. The conversion of vinyl- to formyl- groups is independent of their position on the macrocycle, as we observed oxidative cleavages of both 3-vinyl and 8-vinyl side chains to yield formyl groups. Three new chlorophyll derivatives were synthesised using 8-vinyl chlorophyll a as substrate: 8-vinyl chlorophyll d, [8-formyl]-chlorophyll a, and [3,8-diformyl]-chlorophyll a. The structural and spectral properties will provide a signature that may aid in identification of the novel chlorophyll derivatives in natural systems. The ease of conversion of vinyl- to formyl- in chlorophylls demonstrated here has implications regarding the biosynthetic mechanism of chlorophyll d in vivo.
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