Molecular analysis of cis-prenyl chain elongating enzymes

Kharel, Yugesh; Koyama, Tanetoshi

doi:10.1039/b108934j

Cited by 80 publications

(64 citation statements)

References 60 publications

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“…NDPS1 produces a prenyl diphosphate with a cis configuration, rather than a trans configuration as does GDPS (Fig. 5), possibly because it extracts a different proton from carbon 4 than GDPS does (12,29). We also show that NPP can be used by the monoterpene synthase PHS1 in vitro to catalyze the formation of the same monoterpenes also found, and in similar ratios, in the glands of S. lycopersicum (Fig.…”

Section: Discussionsupporting

confidence: 48%

“…To date, however, only two monoterpene synthases, designated MTS1 and MTS2, have been characterized in tomato (17). The expression of MTS1 in trichomes was shown to be low under normal conditions but highly induced by the application of methyl jasmonate (12). MTS1 protein was shown to catalyze the formation of linalool from GPP in vitro (17), but consistent with its low level of expression under normal conditions, no linalool is observed in tomato trichomes under such conditions (16).…”

mentioning

confidence: 99%

“…They are synthesized from Z-prenyl diphosphates, which are in turn synthesized by cis-prenyltransferases directly from IPP and DMAPP (although in the case of rubber, the starting substrate may be E,E-FPP and IPP) (11). The cis-prenyltransferases are also structurally related to each other but they are not homologous to the trans-prenyltransferases and appear to use a different mechanism (12). Several cis-prenyltransferases have been characterized in bacteria and yeast (13)(14)(15).…”

mentioning

confidence: 99%

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Monoterpenes in the glandular trichomes of tomato are synthesized from a neryl diphosphate precursor rather than geranyl diphosphate

Schilmiller

Schauvinhold

Larson

et al. 2009

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

352

389

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We identified a cis-prenyltransferase gene, neryl diphosphate synthase 1 (NDPS1), that is expressed in cultivated tomato (Solanum lycopersicum) cultivar M82 type VI glandular trichomes and encodes an enzyme that catalyzes the formation of neryl diphosphate from isopentenyl diphosphate and dimethylallyl diphosphate. mRNA for a terpene synthase gene, phellandrene synthase 1 (PHS1), was also identified in these glands. It encodes an enzyme that uses neryl diphosphate to produce ␤-phellandrene as the major product as well as a variety of other monoterpenes. The profile of monoterpenes produced by PHS1 is identical with the monoterpenes found in type VI glands. PHS1 and NDPS1 map to chromosome 8, and the presence of a segment of chromosome 8 derived from Solanum pennellii LA0716 causes conversion from the M82 gland monoterpene pattern to that characteristic of LA0716 plants. The data indicate that, contrary to the textbook view of geranyl diphosphate as the ''universal'' substrate of monoterpene synthases, in tomato glands neryl diphosphate serves as a precursor for the synthesis of monoterpenes.plant biochemistry ͉ terpene synthases ͉ cis-prenyltransferases ͉ biochemical diversity ͉ specialized metabolism

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Section: Discussionsupporting

confidence: 48%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Monoterpenes in the glandular trichomes of tomato are synthesized from a neryl diphosphate precursor rather than geranyl diphosphate

Schilmiller

Schauvinhold

Larson

et al. 2009

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

352

389

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“…With more than 30,000 identified compounds, isoprenoids are the oldest, most abundant, and structurally diverse natural products (Lange et al, 2000;Kharel and Koyama, 2003). In plants, isoprenoids and their derivatives are involved in a number of important processes, including photosynthesis and photoprotection, defense, regulation of growth and development, and attracting animals involved in pollination and seed dispersion (DellaPenna, 1999).…”

mentioning

confidence: 99%

Maize cDNAs Expressed in Endosperm Encode Functional Farnesyl Diphosphate Synthase with Geranylgeranyl Diphosphate Synthase Activity

et al. 2006

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Isoprenoids are the most diverse and abundant group of natural products. In plants, farnesyl diphosphate (FPP) and geranylgeranyl diphosphate (GGPP) are precursors to many isoprenoids having essential functions. Terpenoids and sterols are derived from FPP, whereas gibberellins, carotenoids, casbenes, taxenes, and others originate from GGPP. The corresponding synthases (FPP synthase [FPPS] and GGPP synthase [GGPPS]) catalyze, respectively, the addition of two and three isopentenyl diphosphate molecules to dimethylallyl diphosphate. Maize (Zea mays L. cv B73) endosperm cDNAs encoding isoprenoid synthases were isolated by functional complementation of Escherichia coli cells carrying a bacterial gene cluster encoding all pathway enzymes needed for carotenoid biosynthesis, except for GGPPS. This approach indicated that the maize gene products were functional GGPPS enzymes. Yet, the predicted enzyme sequences revealed FPPS motifs and homology with FPPS enzymes. In vitro assays demonstrated that indeed these maize enzymes produced both FPP and GGPP and that the N-terminal sequence affected the ratio of FPP to GGPP. Their functionality in E. coli demonstrated that these maize enzymes can be coupled with a metabolon to provide isoprenoid substrates for pathway use, and suggests that enzyme bifunctionality can be harnessed. The maize cDNAs are encoded by a small gene family whose transcripts are prevalent in endosperm beginning mid development. These maize cDNAs will be valuable tools for assessing the critical structural properties determining prenyl transferase specificity and in metabolic engineering of isoprenoid pathways, especially in cereal crops.

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“…Natural rubber is a huge linear biopolymer with IPP as the monomeric subunit. As IPP is the monomer of all isoprenoids, rubber biosynthesis is just one of numerous biosynthetic pathways using IPP (Kharel and Koyama, 2003). Plant isoprenoids comprise around 23,000 compounds and are the most diverse class of natural compounds including substances such as gibberellins, carotenoids, chlorophyll side chains, plastochinone side chains, sesquiterpenes, sterols, brassinosteroids, dolichol and mitochondrial ubiquinone side chains (Lichtenthaler et al, 1997;Lichtenthaler, 1999;Newman and Chappell, 1999;Kasahara et al, 2002;Nagata et al, 2002;Kasahara et al, 2004).…”

Section: Rubber Biosynthesismentioning

confidence: 99%