Stereochemistry of trans-phytoene synthesis. Lycopersene as a carotene precursor and a mechanism for the synthesis of cis- and trans-phytoene

Gregonis, D. E.; Rilling, Hans C.

doi:10.1021/bi00704a033

Cited by 49 publications

(19 citation statements)

References 19 publications

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“…coli transformants containing pSM145 were grown to stationary phase and analyzed for GGPP synthase and phytoene synthase activities in cell-free extracts from fresh cultures. The assays were positive for conversion of [14C]IPP and FPP to [14C]GGPP (18) but were negative for synthesis of phytoene from [3H]GGPP (1). Controls without addition of cell extracts or containing extracts from JM101/pARC306N were negative for both activities.…”

Section: Resultsmentioning

confidence: 99%

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The crtE gene in Erwinia herbicola encodes geranylgeranyl diphosphate synthase.

Math

Hearst

Poulter

1992

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

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A cluster of genes essential for the biosynthesis of carotenoids in Erwinia herbicola has been isolated and characterized [Armstrong, G. A., Alberti, M. & Hearst, J. E. (1990) Proc. Natl. Acad. Sci. USA 87,[9975][9976][9977][9978][9979]. Related gene clusters are found in other carotenoid-producing bacteria. Two of these genes, crtB and crtE, have been assigned to enzymes responsible for conversion of geranylgeranyl diphosphate (GGPP) to prephytoene diphosphate and prephytoene diphosphate to phytoene, respectively. We isolated crtE from the Er. herbicola cluster by PCR amplification and cloned the coding region into the Escherichia coli expression vector pARC306N. Es. coli JM101 was transformed with the expression plasmid, and transformants were assayed for GGPP synthase and phytoene synthase activity.

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Section: Resultsmentioning

confidence: 99%

“…1. The first is a cl'-2-3 condensation of two molecules of GGPP to give prephytoene diphosphate, followed by rearrangement of the cyclopropylcarbinyl intermediate to the 1,-1 hydrocarbon phytoene (1). Similar steps are used to synthesize squalene from farnesyl diphosphate (FPP) in the sterol pathway (2).…”

mentioning

confidence: 99%

The crtE gene in Erwinia herbicola encodes geranylgeranyl diphosphate synthase.

Math

Hearst

Poulter

1992

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

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“…blakesleeanus. No tritium was retained in the resulting ciis.-phytoene (Gregonis and Rilling, 1974). However, with a preparation from Mycobacterium sp.…”

Section: :5mentioning

confidence: 98%

“…Phytoene sp. (Gregonis and Rilling, 1974) and Flavobacterium R1560 (Britton et ai., 1980), later enzymes were known to be membrane bound in…”

Section: :6:4 Stereochemistry Of Cyclisationmentioning

confidence: 99%

The photoregulation of carotenoid biosynthesis in Aspergillus giganteus mut. alba

El-Jack

Mackenzie

Bramley

1988

Planta

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“…The mechanism for formation of PT from geranylgeranyl diphosphate is closely related. In this case, two molecules of geranylgeranyl diphosphate condense to give prephytoene diphosphate, which then rearranges to PT (13).…”

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confidence: 99%

Chrysanthemyl diphosphate synthase: Isolation of the gene and characterization of the recombinant non-head-to-tail monoterpene synthase from Chrysanthemum cinerariaefolium

Rivera

Swedlund

King

et al. 2001

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

112

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Chrysanthemyl diphosphate synthase (CPPase) catalyzes the condensation of two molecules of dimethylallyl diphosphate to produce chrysanthemyl diphosphate (CPP), a monoterpene with a non-head-to-tail or irregular c1-2-3 linkage between isoprenoid units. Irregular monoterpenes are common in Chrysanthemum cinerariaefolium and related members of the Asteraceae family. In C. cinerariaefolium, CPP is an intermediate in the biosynthesis of the pyrethrin ester insecticides. CPPase was purified from immature chrysanthemum flowers, and the N terminus of the protein was sequenced. A C. cinerariaefolium cDNA library was screened by using degenerate oligonucleotide probes based on the amino acid sequence to identify a CPPase clone that encoded a 45-kDa preprotein. The first 50 aa of the ORF constitute a putative plastidial targeting sequence. Recombinant CPPase bearing an N-terminal polyhistidine affinity tag in place of the targeting sequence was purified to homogeneity from an overproducing Escherichia coli strain by Ni 2؉ chromatography. Incubation of recombinant CPPase with dimethylallyl diphosphate produced CPP. The diphosphate ester was hydrolyzed by alkaline phosphatase, and the resulting monoterpene alcohol was analyzed by GC͞MS to confirm its structure. The amino acid sequence of CPPase aligns closely with that of the chain elongation prenyltransferase farnesyl diphosphate synthase rather than squalene synthase or phytoene synthase, which catalyze c1-2-3 cyclopropanation reactions similar to the CPPase reaction.

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Stereochemistry of trans-phytoene synthesis. Lycopersene as a carotene precursor and a mechanism for the synthesis of cis- and trans-phytoene

Cited by 49 publications

References 19 publications

The crtE gene in Erwinia herbicola encodes geranylgeranyl diphosphate synthase.

The crtE gene in Erwinia herbicola encodes geranylgeranyl diphosphate synthase.

The photoregulation of carotenoid biosynthesis in Aspergillus giganteus mut. alba

Chrysanthemyl diphosphate synthase: Isolation of the gene and characterization of the recombinant non-head-to-tail monoterpene synthase from Chrysanthemum cinerariaefolium

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