1978
DOI: 10.1039/p19780000845
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Pyrroles and related compounds. Part 39. Structural and biosynthetic studies of the Chlorobium chlorophylls-660 (bacteriochlorophylls c). Incorporations of methionine and porphobilinogen

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. [l4CH3]-, [l3CCH,J -, and [ 13C2H,] -L-methionine are e… Show more

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Cited by 31 publications
(14 citation statements)
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“…Figure 1C shows the natural abundance ,3C NMR spectrum of the Bmph mixture produced by this strain of bacteria. Figure 1B shows the spectrum from the l3C-enriched glutamate feeding; on the basis of previously published 13C assignments (Kenner et al, 1978;Smith et al, 1980;Oh-Hama et al, 1986b), it is clear that Q of glutamate is incorporated into ALA via the C5 pathway.…”
Section: Resultsmentioning
confidence: 70%
See 1 more Smart Citation
“…Figure 1C shows the natural abundance ,3C NMR spectrum of the Bmph mixture produced by this strain of bacteria. Figure 1B shows the spectrum from the l3C-enriched glutamate feeding; on the basis of previously published 13C assignments (Kenner et al, 1978;Smith et al, 1980;Oh-Hama et al, 1986b), it is clear that Q of glutamate is incorporated into ALA via the C5 pathway.…”
Section: Resultsmentioning
confidence: 70%
“…[1-14C]-/-Glutamic acid (0.05 mCi, 0.15 mg) and [2-14C]glycine (0.05 mCi, 0.075 mg) were obtained from New England Nuclear. [I4C-CH3]Methionine (5.28 mCi/mol) was prepared from 14CH3I and homocysteine (Kenner et al, 1978).…”
Section: Methodsmentioning
confidence: 99%
“…48 Lash et al reported the condensation of one dipyrromethane bearing an annulated ring with a second dipyrromethane to form a free base porphyrin containing the five-membered isocyclic ring (V, M = H,H). [49][50][51] Callot's group, drawing on the work of Kenner and Smith and coworkers, 52 reported the acid-catalyzed cyclization of a b-pyrrolic vinyl group to give the analogous nickel porphyrin (V, M = Ni). 53 However, in each of the studies by Lash and by Callot, the resulting macrocycle was a porphyrin, not a chlorin; in other words the skeleton was a 17,18-dehydrophorbine.…”
Section: Synthesismentioning
confidence: 99%
“…Refs. [38][39][40][41][42], the structure of which was confirmed, in one case, by X-ray analysis.f' These studies revealed that the presence of a methyl group at C20 is a necessary though not sufficient prerequisite for photooxidative ring opening of the metal-free chlorin chromophore.?" On the other hand, mechanistic studies using 18 0 labeling with oxygen shown that photooxidation of pheophorbides related to bacteriochlorophylls c to give open-chain acetylbilinones proceed by a mechanism involving only one oxygen molecule, i.e., both oxygen atoms of the lactam and acetyl group in the final product originate from the same oxygen molecule, thus making probable the formation of a dioxetane (33) as an intermediate.t'":'?…”
Section: Photooxidation Of Tetrapyrrole Macrocycles and Their Metal Cmentioning
confidence: 93%