The Carotenoid 7, 8‐Dihydro‐ψ end Group can be Cyclized by the Lycopene Cyclases from the Bacterium <i>Erwinia Uredovora</i> and the Higher Plant <i>Capsicum Annuum</i>

Takaichi, Shinichi; Sandmann, Gerhard; Schnurr, Georg; Satomi, Yoshiko; Suzuki, Akashi; Misawa, Norihiko

doi:10.1111/j.1432-1033.1996.0291t.x

Cited by 57 publications

(47 citation statements)

References 29 publications

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“…At least one species of GSB has an enzyme that can cyclize both the -and 7,8-dihydro-ends of neurosporene (ref. 32; J.A.M., S. P. Romberger, and D.A.B., unpublished data), as can the CrtL-type cyclase from the plant Capsicum annuum and CrtY from Erwinia uredovora (33,34). The lycopene monocyclases from Rhodococcus erythropolis and Deinococcus radiodurans R1 can cyclize only the -end of neurosporene (30), whereas the dicyclase CrtL from Synechococcus sp.…”

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confidence: 99%

Identification of a fourth family of lycopene cyclases in photosynthetic bacteria

Maresca

Graham

et al. 2007

Proc. Natl. Acad. Sci. U.S.A.

133

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A fourth and large family of lycopene cyclases was identified in photosynthetic prokaryotes. The first member of this family, encoded by the cruA gene of the green sulfur bacterium Chlorobium tepidum, was identified in a complementation assay with a lycopene-producing strain of Escherichia coli. Orthologs of cruA are found in all available green sulfur bacterial genomes and in all cyanobacterial genomes that lack genes encoding CrtL-or CrtY-type lycopene cyclases. The cyanobacterium Synechococcus sp. PCC 7002 has two homologs of CruA, denoted CruA and CruP, and both were shown to have lycopene cyclase activity. Although all characterized lycopene cyclases in plants are CrtL-type proteins, genes orthologous to cruP also occur in plant genomes. The CruA-and CruP-type carotenoid cyclases are members of the FixC dehydrogenase superfamily and are distantly related to CrtL-and CrtY-type lycopene cyclases. Identification of these cyclases fills a major gap in the carotenoid biosynthetic pathways of green sulfur bacteria and cyanobacteria.carotenogenesis ͉ carotenoids ͉ cyanobacteria ͉ green sulfur bacteria ͉ photosynthesis C olored carotenoids are found in nearly all photosynthetic species and in a variety of nonphotosynthetic organisms and play roles in light-harvesting, photoprotection, structural maintenance of pigment-protein complexes (1), and membrane structure and fluidity (2). The cyclization of the linear compound lycopene to produce ␣-, ␤-, ␥-, or -carotene is a branch point in carotenoid biosynthetic pathways in many species of bacteria, plants, and fungi (3, 4). The monocyclic ␥-carotene is a precursor to myxoxanthophylls in cyanobacteria (5, 6), is both an intermediate and an end product of carotenogenesis in orange and yellow flowers and fruits (7-10), and is an intermediate in chlorobactene biosynthesis in green sulfur bacteria (GSB) (11-13). Dicyclic ␤-carotene is a major component of photosystems (PS) I and II in cyanobacteria and plants (14,15) and is modified to isorenieratene in brown-colored GSB and some actinomycetes (16,17).Three classes of lycopene cyclases have previously been identified in bacteria: the CrtY-type ␤-cyclases that are found in many carotenogenic proteobacteria (e.g., refs. 18 and 19), Streptomyces spp. (17), and the Chloroflexi; the CrtL family, which includes the ␤-and -cyclases in some cyanobacteria and plants (20,21); and the heterodimeric cyclases of some Gram-positive bacteria (22, 23), which are related to the lycopene cyclases of archaea (24, 25) and halophilic bacteria (26). These classes are distantly related to each other and share only a few conserved motifs, including an N-terminal flavin-binding domain that is found in the first two groups but appears to be missing in the third (27). Carotenoid monocyclases are found in both the CrtY and CrtL families (28-30), and there are no obvious sequence differences between mono-and dicyclases (28).The cyclization of lycopene to ␥-or ␤-carotene is an isomerization reaction, which produces no net change in mass or redox state o...

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mentioning

confidence: 99%

Identification of a fourth family of lycopene cyclases in photosynthetic bacteria

Maresca

Graham

et al. 2007

Proc. Natl. Acad. Sci. U.S.A.

133

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“…Compounds 8-13 possessing characteristic absorption spectra for carotenoids were detected at t R s 9.0, 11.7, 14.3, 14.9, 16.9, and 21.4 min respectively, along with compound 7. These compounds were identified as 15,15 0 Z-phytoene (8), 15,15 0 Z-phytofluene (9), all-E--zeacarotene (10), all-E--carotene (11), all-E-7,8-dihydro--carotene (12), and all-E-neurosporene (13) (Fig. 2).…”

Section: Resultsmentioning

confidence: 99%

“…These carotenoids appeared to have been accumulated by the inhibition of desaturation of acyclic carotene in the biosynthesis of 7 under anaerobic conditions. Carotenoid 12 has been known as the product of carotenogenesis genes expressed in Escherichia coli, 15) but was first isolated from a natural organism. The contents of 7-13 were 3, 4, 0.1, 0.1, 0.4, 0.8, and 0.1 g/g fresh weight of mycelia respectively.…”

Section: Resultsmentioning

confidence: 99%

Biosynthesis of Abscisic Acid by the Direct PathwayviaIonylideneethane in a Fungus,Cercospora cruenta

Inomata

Hirai

Yoshida

et al. 2004

Bioscience, Biotechnology, and Biochemistry

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We examined the biosynthetic pathway of abscisic acid (ABA) after isopentenyl diphosphate in a fungus, Cercospora cruenta. All oxygen atoms at C-1, -1, -1 0 , and -4 0 of ABA produced by this fungus were labeled with 18 O from 18 O 2 . The fungus did not produce the 9Z-carotenoid possessing -ring that is likely a precursor for the carotenoid pathway, but produced new sesquiterpenoids, 2E,4E--ionylideneethane and 2Z,4E--ionylideneethane, along with 2E,4E,6E-allofarnesene. The fungus converted these sesquiterpenoids labeled with 13 C to ABA, and the incorporation ratio of 2Z,4E--ionylideneethane was higher than that of 2E,4E--ionylideneethane. From these results, we concluded that C. cruenta biosynthesized ABA by the direct pathway via oxidation of ionylideneethane with molecular oxygen following cyclization of allofarnesene. This direct pathway via ionylideneethane in the fungus is consistent with that in Botrytis cinerea, except for the positions of double bonds in the rings of biosynthetic intermediates, suggesting that the pathway is common among ABAproducing fungi.

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“…2) (4,5,13,69,105,118,192,199,211). Where gene assembly alone successfully yielded a new pathway branch or extension, the recruited enzyme(s) usually catalyzed transformations later in the pathway.…”

Section: Engineering Pathways By Gene Assemblymentioning

confidence: 99%

“…8b) (32). However, Takaichi et al showed that bacterial and plant lycopene cyclases can cyclize the 7,8-dihydro--end of -carotene and neurosporene (199). Recently, we showed that E. uredovora ␤-cyclase and a plant ε-cyclase can efficiently cyclize nonnatural carotenoids with a C 35 backbone (211).…”

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confidence: 99%

Diversifying Carotenoid Biosynthetic Pathways by Directed Evolution

Umeno

Tobias

Arnold

2005

Microbiol Mol Biol Rev

190

148

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Microorganisms and plants synthesize a diverse array of natural products, many of which have proven indispensable to human health and well-being. Although many thousands of these have been characterized, the space of possible natural products—those that could be made biosynthetically—remains largely unexplored. For decades, this space has largely been the domain of chemists, who have synthesized scores of natural product analogs and have found many with improved or novel functions. New natural products have also been made in recombinant organisms, via engineered biosynthetic pathways. Recently, methods inspired by natural evolution have begun to be applied to the search for new natural products. These methods force pathways to evolve in convenient laboratory organisms, where the products of new pathways can be identified and characterized in high-throughput screening programs. Carotenoid biosynthetic pathways have served as a convenient experimental system with which to demonstrate these ideas. Researchers have mixed, matched, and mutated carotenoid biosynthetic enzymes and screened libraries of these “evolved” pathways for the emergence of new carotenoid products. This has led to dozens of new pathway products not previously known to be made by the assembled enzymes. These new products include whole families of carotenoids built from backbones not found in nature. This review details the strategies and specific methods that have been employed to generate new carotenoid biosynthetic pathways in the laboratory. The potential application of laboratory evolution to other biosynthetic pathways is also discussed

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The Carotenoid 7, 8‐Dihydro‐ψ end Group can be Cyclized by the Lycopene Cyclases from the Bacterium Erwinia Uredovora and the Higher Plant Capsicum Annuum

Cited by 57 publications

References 29 publications

Identification of a fourth family of lycopene cyclases in photosynthetic bacteria

Identification of a fourth family of lycopene cyclases in photosynthetic bacteria

Biosynthesis of Abscisic Acid by the Direct PathwayviaIonylideneethane in a Fungus,Cercospora cruenta

Diversifying Carotenoid Biosynthetic Pathways by Directed Evolution

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