Cloning and functional expression in Escherichia coli of a cyanobacterial gene for lycopene cyclase, the enzyme that catalyzes the biosynthesis of β‐carotene

Cunningham, Francis X.; Chamovitz, Daniel; Misawa, Norihiko; Gantt, Elisabeth; Hirschberg, Joseph

doi:10.1016/0014-5793(93)80980-9

Cited by 110Plant biochemistry and biosynthesisPhotosynthetic Processes and MechanismsMicrobial Metabolism and Applications

Cloning and functional expression in Escherichia coli of a cyanobacterial gene for lycopene cyclase, the enzyme that catalyzes the biosynthesis of β‐carotene

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Cunningham, Francis X., Chamovitz, Daniel, Misawa, Norihiko, Gantt, Elisabeth, Hirschberg, Joseph·1993·FEBS Letters

DOI 10.1016/0014-5793(93)80980-9

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Abstract

Carotenoids with cyclic end groups are essential components of the photosynthetic membrane in all known oxygenic photosynthetic organisms. These yellow pigments serve the vital role of protecting against potentially lethal photo‐oxidative damage. Many of the enzymes and genes of the carotenoid biosynthetic pathway in cyanobacteria, algae and plants remain to be isolated or identified. We have cloned a cyanobacterial gene encoding lycopene cyclase, an enzyme that converts the acyclic carotenoid lycopene to the bicyclic molecule β‐carotene. The gene was identified through the use of an experimental herbicide, 2‐(4‐methylphenoxy)triethylamine hydrochloride (MPTA), that prevents the cyclization of lycopene in plants and cyanobacteria. Chemically‐induced mutants of the cyanobacterium Synechococcus sp. PCC7942 were selected for resistance to MPTA, and a mutation responsible for this resistance was mapped to a genomic DNA region of 200 bp by genetic complementation of the resistance in wild‐type cells. A 1.5 kb genomic DNA fragment containing this MPTA‐resistance mutation was expressed in a lycopene‐accumulating strain of Escherichia coli. The conversion of lycopene to β‐carotene in these cells demonstrated that this fragment encodes the enzyme lycopene cyclase. The results indicate that a single gene product, designated lcy, catalyzes both of the cyclization reactions that are required to produceβ‐carotene from lycopene, and prove that this enzyme is a target site of the herbicide MPTA. The cloned cyanobacterial lcy gene hybridized well with genomic DNA from eukaryotic algae, thus it will enable the identification and cloning of homologous genes for lycopene cyclase in algae and plants.

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Lycopene is transformed into β-carotene by lycopene-β-cyclase, which depends on NADPH.
“Lycopene, a compound with a red hue conferred by a set of 11 conjugated double bonds, is transformed into β,β-carotene by an enzyme known as lycopene-β-cyclase.126,127 Although not a reaction that involves net redox changes, the cyclization performed by lycopene-β-cyclase is dependent on an NAPDH cofactor.128”
From Chemistry of the Retinoid (Visual) Cycle (2014) · cites this paper as [127]
Citation 128 is attached to the NADPH-dependence claim, not the preceding conversion claim. The Introduction and Discussion describe lycopene cyclase converting lycopene to β-carotene, but the passages found when searching for NADPH, reducing cofactors, and cofactor requirements do not address whether that reaction depends on NADPH. (LLM, conf=0.74)
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Molecular cloning: A laboratory manual
Deininger, P. L. (1990) · Analytical Biochemistry · doi:10.1016/0003-2697(90)90595-z · Cited by 84,684 · see citing works
Photoprotection and Other Responses of Plants to High Light Stress
Demmig‐Adams, B., & Adams, W. W. (1992) · Annual Review of Plant Physiology and Plant Molecular Biology · doi:10.1146/annurev.pp.43.060192.003123 · Cited by 2,424 · see citing works
Metabolism and Physiology of Abscisic Acid
Zeevaart, J. A. D., & Creelman, R. A. (1988) · Annual Review of Plant Physiology and Plant Molecular Biology · doi:10.1146/annurev.pp.39.060188.002255 · Cited by 1,427 · see citing works
The Biochemistry of the Carotenoids
Goodwin, T. W. (1984) · Springer eBooks · doi:10.1007/978-94-009-5542-4 · Cited by 1,010 · see citing works
[85] Construction of specific mutations in photosystem II photosynthetic reaction center by genetic engineering methods in Synechocystis 6803
Williams, J. G. (1988) · Methods in enzymology on CD-ROM/Methods in enzymology · doi:10.1016/0076-6879(88)67088-1 · Cited by 978 · see citing works
Research in Photosynthesis
(1992) · Springer eBooks · doi:10.1007/978-94-009-0383-8 · Cited by 898 · see citing works
The light‐harvesting and protective functions of carotenoids in photosynthetic membranes
Siefermann‐Harms, D. (1987) · Physiologia Plantarum · doi:10.1111/j.1399-3054.1987.tb09240.x · Cited by 636 · see citing works
The Biochemistry of the Carotenoids
Goodwin, T. W. (1980) · Springer eBooks · doi:10.1007/978-94-009-5860-9 · Cited by 613 · see citing works
Elucidation of the Erwinia uredovora carotenoid biosynthetic pathway by functional analysis of gene products expressed in Escherichia coli
Misawa, N., Nakagawa, M., Kobayashi, K., Yamano, S., Izawa, Y., Nakamura, K., & Harashima, K. (1990) · Journal of Bacteriology · doi:10.1128/jb.172.12.6704-6712.1990 · Cited by 596 · see citing works
Self-citation
[38] Antioxidant effects of carotenoids in Vivo and in Vitro: An overview
Palozza, P., & Krinsky, N. I. (1992) · Methods in enzymology on CD-ROM/Methods in enzymology · doi:10.1016/0076-6879(92)13142-k · Cited by 472 · see citing works
The aba mutant of Arabidopsis thaliana is impaired in epoxy-carotenoid biosynthesis.
Rock, C. D., & Zeevaart, J. A. D. (1991) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.88.17.7496 · Cited by 358 · see citing works
Nucleotide sequence, organization, and nature of the protein products of the carotenoid biosynthesis gene cluster of Rhodobacter capsulatus
Armstrong, G. A., Alberti, M., Leach, F., & Hearst, J. E. (1989) · Molecular and General Genetics MGG · doi:10.1007/bf00334364 · Cited by 357 · see citing works
A one-tube plasmid DNA mini-preparation suitable for sequencing
Sal, G. D., Manfioletti, G., & Schneider, C. (1988) · Nucleic Acids Research · doi:10.1093/nar/16.20.9878 · Cited by 271 · see citing works
Target Sites of Herbicide Action
Böger, P., & Sandmann, G. (2020) · CRC Press eBooks · doi:10.1201/9781003068280 · Cited by 260 · see citing works
A single polypeptide catalyzing the conversion of phytoene to zeta-carotene is transcriptionally regulated during tomato fruit ripening.
Pecker, I., Chamovitz, D., Linden, H., Sandmann, G., & Hirschberg, J. (1992) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.89.11.4962 · Cited by 196 · see citing works
Self-citation
New trends in photobiology
Yasushi, K. (1991) · Journal of Photochemistry and Photobiology B: Biology · doi:10.1016/1011-1344(91)80165-e · Cited by 171 · see citing works
Stable integration of foreign DNA into the chromosome of the cyanobacterium Synechococcus R2
Williams, J. G., & Szalay, A. A. (1983) · Gene · doi:10.1016/0378-1119(83)90129-4 · Cited by 167 · see citing works
The molecular basis of resistance to the herbicide norflurazon
Chamovitz, D., Pecker, I., & Hirschberg, J. (1991) · Plant Molecular Biology · doi:10.1007/bf00016069 · Cited by 156 · see citing works
Self-citation
Carotenoid biosynthesis: Isolation and characterization of a bifunctional enzyme catalyzing the synthesis of phytoene
Dogbo, O., Laferriére, A., d’Harlingue, A., et al. (1988) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.85.19.7054 · Cited by 143 · see citing works
A tomato gene expressed during fruit ripening encodes an enzyme of the carotenoid biosynthesis pathway.
Bartley, G. E., Viitanen, P. V., Bacot, K. O., & Scolnik, P. A. (1992) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(18)42724-x · Cited by 136 · see citing works
Molecular cloning and expression in photosynthetic bacteria of a soybean cDNA coding for phytoene desaturase, an enzyme of the carotenoid biosynthesis pathway.
Bartley, G. E., Viitanen, P. V., Pecker, I., Chamovitz, D., Hirschberg, J., & Scolnik, P. A. (1991) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.88.15.6532 · Cited by 134 · see citing works
Self-citation
Characterization and molecular cloning of a flavoprotein catalyzing the synthesis of phytofluene and ζ‐carotene in Capsicum chromoplasts
Hugueney, P., Römer, S., Kuntz, M., & Camara, B. (1992) · European Journal of Biochemistry · doi:10.1111/j.1432-1033.1992.tb17302.x · Cited by 110 · see citing works
Biochemical characterization of transgenic tomato plants in which carotenoid synthesis has been inhibited through the expression of antisense RNA to pTOM5
Bramley, P. M., Teulières, C., Blain, I., Bird, C. R., & Schuch, W. (1992) · The Plant Journal · doi:10.1111/j.1365-313x.1992.00343.x · Cited by 106 · see citing works
Molecular cloning and expression in Escherichia coli of a cyanobacterial gene coding for phytoene synthase, a carotenoid biosynthesis enzyme
Chamovitz, D., Misawa, N., Sandmann, G., & Hirschberg, J. (1992) · FEBS Letters · doi:10.1016/0014-5793(92)80310-d · Cited by 99 · see citing works
Self-citation
Functional Complementation in Escherichia coli of Different Phytoene Desaturase Genes and Analysis of Accumulated Carotenes
Linden, H., Misawa, N., Chamovitz, D., Pecker, I., Hirschberg, J., & Sandmann, G. (1991) · Zeitschrift für Naturforschung C · doi:10.1515/znc-1991-11-1219 · Cited by 96 · see citing works
Self-citation
[80] Mutagenesis of cyanobacteria by classical and gene-transfer-based methods
Golden, S. S. (1988) · Methods in enzymology on CD-ROM/Methods in enzymology · doi:10.1016/0076-6879(88)67083-2 · Cited by 71 · see citing works
Sequence of pTOM5, a ripening related cDNA from tomato
Ray, J. A., Bird, C. R., Maunders, M. J., et al. (1987) · Nucleic Acids Research · doi:10.1093/nar/15.24.10587 · Cited by 69 · see citing works
Isolation of a carotenoid biosynthesis gene coding for ζ-carotene desaturase fromAnabaenaPCC 7120 by heterologous complementation
Linden, H., Vioque, A., & Sandmann, G. (1993) · FEMS Microbiology Letters · doi:10.1111/j.1574-6968.1993.tb05941.x · Cited by 67 · see citing works
Carotenoid biosynthesis in Blakeslea trispora
Hsu, W. J., Yokoyama, H., & Coggins, C. W. (1972) · Phytochemistry · doi:10.1016/0031-9422(72)80090-6 · Cited by 66 · see citing works
The in Vitro Biosynthesis of Carotenoids
Bramley, P. M. (1985) · Advances in lipid research · doi:10.1016/b978-0-12-024921-3.50013-7 · Cited by 65 · see citing works
?-Carotene synthesis in isolated chromoplasts from Narcissus pseudonarcissus
Beyer, P., Kreuz, K., & Kleinig, H. (1980) · Planta · doi:10.1007/bf00390182 · Cited by 65 · see citing works
In vitro expression and activity of lycopene cyclase and β‐carotene hydroxylase from Erwinia herbicola
Hundle, B. S., O'Brien, D. A., Beyer, P., Kiemig, H., & Hearst, J. E. (1993) · FEBS Letters · doi:10.1016/0014-5793(93)81188-6 · Cited by 60 · see citing works
Enzyme-Kinetic Studies on the Interaction of Norflurazon with Phytoene Desaturase
Sandmann, G., Linden, H., & Böger, P. (1989) · Zeitschrift für Naturforschung C · doi:10.1515/znc-1989-9-1015 · Cited by 54 · see citing works
Cloning a Gene Coding for Norflurazon Resistance in Cyanobacteria
Chamovitz, D., Pecker, I., Sandmann, G., et al. (1990) · Zeitschrift für Naturforschung C · doi:10.1515/znc-1990-0531 · Cited by 47 · see citing works
Self-citation
Effects of Carotenoid Administration on Bladder Cancer Prevention
Mathews‐Roth, M. M., Lausen, N., Drouin, G., et al. (2009) · Oncology · doi:10.1159/000226922 · Cited by 38 · see citing works
Induction of carotenogenesis in cultured cells of Lycopersicon esculentum
Fosket, D. E., & Radin, D. N. (1983) · Plant Science Letters · doi:10.1016/0304-4211(83)90215-8 · Cited by 28 · see citing works
CHEMICAL REGULATION OF CAROTENOID BIOSYNTHESIS
Yokoyama, H., Hsu, W. J., Poling, S. M., et al. (1982) · Elsevier eBooks · doi:10.1016/b978-0-08-026224-6.50030-9 · Cited by 14 · see citing works
Effects of in vivo inhibitors of carotene biosynthesis on the synthesis of carotenes by a soluble tomato plastid enzyme system
Bucholtz, M. L., Maudinas, B., & Porter, J. W. (1977) · Chemico-Biological Interactions · doi:10.1016/0009-2797(77)90098-9 · Cited by 9 · see citing works

Flagged first, then by citations

Research works printed but not linked: 9

Rock. C.D. and Zeevaart, J.A.D. (1991) Proc. Natl. Acad. Sci. USA 88. 1496-7499.
Britton. G. (1988) m: Plant Pigments (Goodwin, T.W. ed.) pp. 133-180. Academic Press, New York
Spurgeon, S.L. and Porter, J.W. (1980) m. Biochemistry of Iso- prenold Compounds (Porter, J.W. and Spurgeon, S.L. eds.) pp. l-122. Wiley, New York.
Dogbo. O., Lafernkre, A., d'Harlingue. A. and Camara, B. (1988) Proc. Natl. Acad SCI. USA X5, 70547058.
Pecker. I.. Chamovitz, D., Linden, H.. Sandmann. G. and Hirschberg, J (1992) Proc. Nat1 Acad. Sci. USA 89.4962-4966.
Bartley, G.E., Viitanen, P.V., Pecker, I., Chamovitz. D., Hirsch- berg, J. and Scolnik, P.A. (1991) Proc. Natl. Acad. Sci. USA 88, 6532-6536.
Yokoyama, H.. Hsu, W.J.. Poling. S.M. and Hayman. E. (1982) m: Carotenold Chemistry and Biochemistry (Brltton, G. and Goodwm, T.W. eds ) pp. 371-385, Pergamon Press, Oxford.
Cunmngham, Jr. F.X. (1985) Carotenolds of ElcgLenu gracrbs Klebs var bacilluris Con: photoaomerization. biosynthesis, local- ization and association with chlorophylls and poiypeptides in chlorophyll-protein complexes, Ph.D. Thesis. Brandise Univer- sity.
Beyer. P. (1989) in, Physiology. Biochemistry and Genetics of Nongreen Plastlds (Boyer, C.D., Shanon. J.C. and Hardison. R C. eds.) pp. 157-170, American Society of Plant Physiology.

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Authors: Cunningham, F. X., Chamovitz, D., Misawa, N., Gantt, E., & Hirschberg, J.
Affiliations: Hebrew University of Jerusalem (IL)
Kirin (Japan) (JP)
University of Maryland, College Park (US)
ORCID: Chamovitz, Daniel
Misawa, Norihiko
Hirschberg, Joseph
Venue: FEBS Letters
Publisher: Wiley
Published: 1993-08-09
Volume: 328
Issue: 1-2
Pages: 130-138
ISSN: 0014-5793 (ISSN-L)
1873-3468
DOI: 10.1016/0014-5793(93)80980-9
OpenAlex: W2105945118
Cited by: 110
References: 38
Citations by year: 2026: 1 · 2024: 1 · 2023: 2 · 2022: 6 · 2021: 5 · 2020: 2 · 2019: 2 · 2018: 4 · 2017: 4 · 2016: 6 · 2015: 3 · 2014: 2 · 2013: 4 · 2012: 2
FWCI: 1.93
Type: journal article
Language: en
Open access: bronze
doi.org
Licence: onlinelibrary.wiley.com/termsAndConditions#vor (vor, 3017 d)
Locations: FEBS Letters (publishedVersion)
PubMed (publishedVersion)
Topics: Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Plant biochemistry and biosynthesis
Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Photosynthetic Processes and Mechanisms
Life Sciences › Biochemistry, Genetics and Molecular Biology › Biotechnology › Microbial Metabolism and Applications
Keywords: lycopene cyclase, β-carotene biosynthesis, carotenoid biosynthesis, cyanobacteria, Synechococcus elongatus PCC 7942, herbicide resistance, gene complementation, gene cloning, heterologous expression in Escherichia coli
MeSH terms: Lycopene, Cyanobacteria, Carotenoids, Chromatography, High Pressure Liquid, Cloning, Molecular, DNA, Bacterial, Drug Resistance, Microbial, Escherichia coli, Ethylamines, Isomerases, Mutation, Plasmids, Transfection, Gene Expression Regulation, Enzymologic, beta Carotene, Intramolecular Lyases

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Cloning and functional expression in Escherichia coli of a cyanobacterial gene for lycopene cyclase, the enzyme that catalyzes the biosynthesis of β‐carotene

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