Prephytoene pyrophosphate. New intermediate in the biosynthesis of carotenoids

Altman, Lawrence J.; Ash, Lucienne; Kowerski, R. C.; Epstein, William W.; Larsen, Bjørn; Rilling, Hans C.; Muscio, F.; Gregonis, D. E.

doi:10.1021/ja00764a073

Cited by 60 publications

(18 citation statements)

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“…With the discovery of prephytoene pyrophosphate (8), and the development of analytical techniques for the isolation and identification of the terpenyl pyrophosphates from other systems, it was reasonable to try to elucidate further the specific reactions affected by the al-2 and al-3 mutations.…”

Section: Introductionmentioning

confidence: 99%

The terpenyl pyrophosphates of wild type and tetraterpene mutants ofNeurospora crassa

Kushwaha

Kates

Renaud

et al. 1978

Lipids

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Mutations to two albino loci ofNeurospora (al‐2 andal‐3) are known to block tetraterpene synthesis prior to phytoene but after farnesyl pyrophosphate. Analysis of the terpenyl pyrophosphates labeled with [214C] mevalonic acid revealed the presence of radioactive prephytoene, pyrophosphate in both albino mutants and in the corresponding wild type strain. Theal‐2 andal‐3 mutations are thus associated with lesions between prephytoene pyrophosphate and phytoene.

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Section: Introductionmentioning

confidence: 99%

The terpenyl pyrophosphates of wild type and tetraterpene mutants ofNeurospora crassa

Kushwaha

Kates

Renaud

et al. 1978

Lipids

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“…This sequence of reactions is common to all terpenoids, including other plastid terpenoids (chlorophylls, plastoquinones, tocopherols, phylloquinones, and polyterpenes). On the other hand, the next two steps, in which prephytoene diphosphate (6) and phytoene (7) are formed, are catalyzed by the first carotenoid-specific enzymes in the pathway, tentatively termed "geranylgeranyl pyrophosphate geranylgeranyltransferase" and "phytoene synthase" (7) since they have been neither isolated nor characterized previously from any other source (5,8,9). Therefore, the identification of the enzyme components catalyzing these two steps is crucial for our understanding of the molecular mechanism of carotenoid biosynthesis and of its regulation; a particularly interesting 2 The present paper answers this question.…”

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confidence: 99%

Carotenoid biosynthesis: Isolation and characterization of a bifunctional enzyme catalyzing the synthesis of phytoene

Dogbo

Laferrière

d’Harlingue

et al. 1988

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

137

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Phytoene is the frst C40 intermediate in the biogenesis of carotenoids. It is formed by two enzyme activities, catalyzing (i) the coupling of two molecules of geranylgeranyl diphosphate to yield prephytoene diphosphate and (i) the conversion of prephytoene diphosphate into phytoene. We show now, with Capsicum chromoplast stroma, that the overall activity resides in a single protein, which has been purified to homogeneity by affinity chromatography. The monomeric structure and the molecular size (Mr 47,500) were demonstrated by NaDodSO4/PAGE and glycerol gradient centrifugation. Further characterization was achieved by using specific antibodies which allowed immunofractionation and immunoprecipitation of the enzymatic activity from chromoplast stroma. The two reactions followed conventional MichaelisMenten kinetics, with Km values of 0.30 ,.M and 0.27 IAM, respectively, for geranylgeranyl diphosphate and prephytoene diphosphate. The activity of the enzyme depends strictly upon the presence ofMn2. This selectivity may be one of the factors regulating the competition with potentially rival enzymes converting geranylgeranyl diphosphate into other plastid terpenoids. The two enzymatic reactions were inhibited by inorganic pyrophosphate and by the arginine-specific reagent hydroxyphenylglyoxal. In no instance were the two reactions kinetically uncoupled. These properties strongly suggest that the same enzyme catalyzes the two consecutive reactions, and we propose to name it phytoene synthase.Carotenoids are required for the normal differentiation and function of plastids. Phytoene, the first C40 intermediate in the carotenoid pathway, is synthesized by a soluble enzymatic complex localized in plastid stroma (1)(2)(3)(4)(5), by the multistep process outlined in Scheme I. The early steps, for which the individual enzymes were recently isolated and purified (6), are the isomerization of isopentenyl diphosphate (1) into dimethylallyl diphosphate (2), followed by three prenylations forming successively geranyl diphosphate (3), farnesyl diphosphate (4), and geranylgeranyl diphosphate (5). This sequence of reactions is common to all terpenoids, including other plastid terpenoids (chlorophylls, plastoquinones, tocopherols, phylloquinones, and polyterpenes). On the other hand, the next two steps, in which prephytoene diphosphate (6) and phytoene (7) are formed, are catalyzed by the first carotenoid-specific enzymes in the pathway, tentatively termed "geranylgeranyl pyrophosphate geranylgeranyltransferase" and "phytoene synthase" (7) since they have been neither isolated nor characterized previously from any other source (5,8,9). Therefore, the identification of the enzyme components catalyzing these two steps is crucial for our understanding of the molecular mechanism of carotenoid biosynthesis and of its regulation; a particularly interesting The present paper answers this question. We show, with Capsicum chromoplasts, previously selected for studies of carotenogenesis (3,(10)(11)(12), that a single monomeric protein ...

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“…Phytoene is formed via the C4Q cyclopropane intermediate, prephytoene pyrophosphate (PPPP) (Altman et al, 1972). In higher plants 15-cis-phytoene is generally found, the trans isomer occurring in other organisms.…”

Section: Formation Of Phytoenementioning

confidence: 99%

Pigments in Vegetables

Gross¹

1991

246

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Prephytoene pyrophosphate. New intermediate in the biosynthesis of carotenoids

Cited by 60 publications

References 0 publications

The terpenyl pyrophosphates of wild type and tetraterpene mutants ofNeurospora crassa

The terpenyl pyrophosphates of wild type and tetraterpene mutants ofNeurospora crassa

Carotenoid biosynthesis: Isolation and characterization of a bifunctional enzyme catalyzing the synthesis of phytoene

Pigments in Vegetables

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