Title
Pyrroles and related compounds. Part 39. Structural and biosynthetic studies of the Chlorobium chlorophylls-660 (bacteriochlorophylls c). Incorporations of methionine and porphobilinogen
Document Type
Article
Publication Date
1-1-1978
Abstract
Treatment of the phaeofarnesins (4) isolated from the Chlorobium chlorophylls-660 (ex. Chloropseudomonas ethylicum) with sulphuric acid in methanol gives the methyl phaeophorbides (1) which can be dehydrated by refluxing in benzene in the presence of acid to afford the 2-vinyl derivatives (2); prolonged refluxing gives the novel cyclised compounds (6). By-products from handling the pigments are the 8′-acetylbilitrienes (5), obtained by photo-oxygenation. [14CH3]-, [13CH 3]-, and [13C2H3]-L-methionine are efficiently incorporated into the Chlorobium chlorophylls-660, showing that the extra methylation present in the δ-methyl, 4-isobutyl, 4-n-propyl, and 5-ethyl groups of these pigments is methionine derived. Using 6-14C labelled material, porphobilinogen is also confirmed as an important building block in these bacterial chlorophylls.
Publication Source (Journal or Book title)
Journal of the Chemical Society, Perkin Transactions 1
First Page
845
Last Page
852
Recommended Citation
Kenner, G., Rimmer, J., Smith, K., & Unsworth, J. (1978). Pyrroles and related compounds. Part 39. Structural and biosynthetic studies of the Chlorobium chlorophylls-660 (bacteriochlorophylls c). Incorporations of methionine and porphobilinogen. Journal of the Chemical Society, Perkin Transactions 1 (8), 845-852. https://doi.org/10.1039/p19780000845