Zincphyrin, a novel coproporphyrin III with zinc from Streptomyces sp.

Toriya, Minoru; Yaginuma, Satoshi; Murofushi, Sakae; Ogawa, Kiyoshi; Muto, Naoki; Hayashi, Masahito; Matsumoto, K

doi:10.7164/antibiotics.46.196

Cited by 24 publications

(15 citation statements)

References 4 publications

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“…In the case of C. glutamicum , porphyrin production has only been reported as an iron additive for heme production by expressing ALA synthase 39 . In particular, study on the biosynthesis of Zn-porphyrin has been rarely reported, and none reported Zn-porphyrin production in a genetically engineered strain 24 , 40 .…”

Section: Introductionmentioning

confidence: 99%

Biosynthesis of organic photosensitizer Zn-porphyrin by diphtheria toxin repressor (DtxR)-mediated global upregulation of engineered heme biosynthesis pathway in Corynebacterium glutamicum

Joo

Hyeon

et al. 2018

Sci Rep

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Zn-porphyrin is a promising organic photosensitizer in various fields including solar cells, interface and biomedical research, but the biosynthesis study has been limited, probably due to the difficulty of understanding complex biosynthesis pathways. In this study, we developed a Corynebacterium glutamicum platform strain for the biosynthesis of Zn-coproporphyrin III (Zn-CP III), in which the heme biosynthesis pathway was efficiently upregulated. The pathway was activated and reinforced by strong promoter-induced expression of hemAM (encoding mutated glutamyl-tRNA reductase) and hemL (encoding glutamate-1-semialdehyde aminotransferase) genes. This engineered strain produced 33.54 ± 3.44 mg/l of Zn-CP III, while the control strain produced none. For efficient global regulation of the complex pathway, the dtxR gene encoding the transcriptional regulator diphtheria toxin repressor (DtxR) was first overexpressed in C. glutamicum with hemAM and hemL genes, and its combinatorial expression was improved by using effective genetic tools. This engineered strain biosynthesized 68.31 ± 2.15 mg/l of Zn-CP III. Finally, fed-batch fermentation allowed for the production of 132.09 mg/l of Zn-CP III. This titer represents the highest in bacterial production of Zn-CP III reported to date, to our knowledge. This study demonstrates that engineered C. glutamicum can be a robust biotechnological model for the production of photosensitizer Zn-porphyrin.

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Section: Introductionmentioning

confidence: 99%

Biosynthesis of organic photosensitizer Zn-porphyrin by diphtheria toxin repressor (DtxR)-mediated global upregulation of engineered heme biosynthesis pathway in Corynebacterium glutamicum

Joo

Hyeon

et al. 2018

Sci Rep

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“…rubrum is increased with decreasing pH of the culture medium as noted above. However, some chemotrophic bacteria are known to produce zinc complexes of porphyrins in growth media at neutral pH (Kajiwara et al, 1995;Toriya et al, 1993) and the intracellular pH of acidophilic bacteria including Acidiphilium was reported to be neutral in general (Hsung and Haug, 1975;Matin, 1999;Zychlinsky and Matin, 1983a, b). Although it is likely that acidic habitats may provide more favorable conditions for ZnBChl production by photosynthetic organisms living therein, the relationship between specific Zn-BChl requirement for photosynthesis and acidic conditions as natural habitats awaits further study.…”

Section: Concluding Remarks and Future Perspectivesmentioning

confidence: 99%

Aerobic anoxygenic photosynthetic bacteria with zinc-bacteriochlorophyll.

Hiraishi

Shimada

2001

J. Gen. Appl. Microbiol.

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IntroductionChlorophylls (Chls) and bacteriochlorophylls (BChls) are porphyrin derivatives chelated with magnesium, and represent a class of lipophilic pigments involved in natural photosynthesis. There has been no rational explanation for why extant phototrophic organisms have used Mg exclusively as the central metal with which the chlorophyllous pigments are complexed. Apart from this question, phototrophic organisms that use Chls or BChls containing metals other than Mg were unknown for a long time. Recently, this common understanding of natural photosynthesis was unexpectedly modified by the new finding that a novel purple pigment, zinc-chelated-BChl (Zn-BChl) (for abbreviations, see Takaichi et al. (1999)), was discovered in a specific group of obligately aerobic bacteria (Hiraishi et al., 1998;Wakao et al., 1996Wakao et al., , 1999.It has been satisfactorily demonstrated that BChls are present not only in facultatively and obligately anaerobic anoxygenic phototrophic bacteria but also in large numbers of species of obligately aerobic bacteria Naturally occurring chlorophyllous pigments, which function as the cofactor in the early photochemical reaction of photosynthesis, have been proven beyond question to be magnesium-complexed porphyrin derivatives. Phototrophic organisms that use (bacterio)chlorophylls ([B]Chls)containing metals other than Mg were unknown for a long time. This common knowledge of natural photosynthesis has recently been modified by the striking finding that a novel purple pigment, zinc-chelated-BChl (Zn-BChl) a, is present as the major and functional pigment in species of the genus Acidiphilium. Acidiphilium species are obligately acidophilic chemoorganotrophic bacteria that grow and produce photopigments only under aerobic conditions. Although the mechanism of photosynthesis with Zn-BChl a in Acidiphilium species is similar to that seen in common purple bacteria, some characteristic photosynthetic features of the acidophilic bacteria are also found. The discovery of natural photosynthesis with Zn-BChl has not only provided a new insight into our understanding of bacterial photosynthesis but also raised some interesting questions to be clarified. The major questions are why the acidophilic bacteria have selected ZnBChl for their photosynthesis and how they synthesize Zn-BChl and express photosynthetic activity with it in their natural habitats. In this article we review the current knowledge of the biology of Acidiphilium as aerobic photosynthetic bacteria with Zn-BChl a and discuss the interesting topics noted above.

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“…Growth factor C was unambiguously identified by direct comparison with zincphyrin, 13 which was synthesized from coproporphyrin III and Zn(OAc) 2 (Table 1). The difference between zincphyrin (C) and F in molecular formula was CH 2 (14 mass units), which suggested that growth factor F was a methyl ester of zincphyrin (C).…”

Section: Structure Identifications Of Growth Factors a B C D E And Fmentioning

confidence: 99%

“…The n-BuOH extract was evaporated in vacuo to yield 1.6 mg of a dark reddish compound reported as zincphyrin. 13 Growth factor C was identified as zincphyrin by HPLC, UV-visible spectral pattern, color, ESI-MS, 1 H and 13 C NMR chemical shifts, and growth-promoting activity (Table 1 and Supplementary Table 3). …”

Section: Synthesis Of Zinc Coproporphyrin I and Its Identification Asmentioning

confidence: 99%

Zincmethylphyrins and coproporphyrins, novel growth factors released by Sphingopyxis sp., enable laboratory cultivation of previously uncultured Leucobacter sp. through interspecies mutualism

et al. 2015

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We have identified coproporphyrins including structurally new zincmethylphyrins I and III as growth factors A-F for the previously uncultured bacterial strain, Leucobacter sp. ASN212, from a supernatant of 210 l of Sphingopyxis sp. GF9 culture. Growth factors A-F induced significant growth of strain ASN212 at the concentrations of picomolar to nanomolar which would otherwise be unculturable in liquid medium or on agar plate. More interestingly, we found that the growth factors functioned as self-toxic compounds for the growth-factor producing strain GF9 at the picomolar to nanomolar levels. As a variety of bacteria could potentially produce coproporphyrins, our findings suggest that these compounds function as a novel class of signal molecules across a boundary at phylum level in the complex bacterial communities.

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Zincphyrin, a novel coproporphyrin III with zinc from Streptomyces sp.

Cited by 24 publications

References 4 publications

Biosynthesis of organic photosensitizer Zn-porphyrin by diphtheria toxin repressor (DtxR)-mediated global upregulation of engineered heme biosynthesis pathway in Corynebacterium glutamicum

Biosynthesis of organic photosensitizer Zn-porphyrin by diphtheria toxin repressor (DtxR)-mediated global upregulation of engineered heme biosynthesis pathway in Corynebacterium glutamicum

Aerobic anoxygenic photosynthetic bacteria with zinc-bacteriochlorophyll.

Zincmethylphyrins and coproporphyrins, novel growth factors released by Sphingopyxis sp., enable laboratory cultivation of previously uncultured Leucobacter sp. through interspecies mutualism

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