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Geranylgeranyl diphosphate

Diterpenoids are derived biosynthetically from geranylgeranyl diphosphate (GGPP), which is itself biosynthesized by reaction of farnesvl diphosphate with isopentenyl diphosphate. Show the structure of GGPP, and propose a mechanism for its biosynthesis horn FPP and IPP. [Pg.1098]

Propose a structure for cembrene that is consistent with its formation from geranylgeranyl diphosphate. [Pg.1098]

S-prenylation is the most recent of the four major types of lipid modifications to be described. As with -acylation, S-prenylation is posttranslational. The lipid substrates for these modifications are farnesyl diphosphate and geranylgeranyl diphosphate. The mechanism... [Pg.692]

MATH s K, HEARST J E and pouLTER c D (1992) The crtE gene mErwinia herbicola encodes geranylgeranyl diphosphate synthase , Proc Natl Acad Sci, 89, 6761-4. [Pg.277]

Cervantes-Cervantes, M. et al., Maize cDNAs expressed in endosperm encode functional famesyl diphosphate synthase with geranylgeranyl diphosphate synthase activity, Plant Physiol. 220, 2006. [Pg.390]

Okada, K. et al., Five geranylgeranyl diphosphate synthases expressed in different organs are localized into three subcellular compartments in Arabidopsis, Plant Physiol. 122, 1045, 2000. [Pg.390]

Koepp, A.E., Hezari, M., Zajicek, J. etal. (1995) Cyclization of geranylgeranyl diphosphate to taxa-4(5),l 1(12)-diene is the committed step of Taxol biosynthesis in Pacific yew. Journal of Biological Chemistry, 270, 8686-8690. [Pg.285]

By using an elegant 13C-labeling study that involved incubation of Phoma sp. with 1-13C and 1,2-13C acetate, Oikawa et al. [9], were able to isolate the proposed biosynthetic intermediate phomactatriene (or Sch 49026), with 13C incorporation from singly labeled acetate units as indicated by in Fig. 8.3. Phomactatriene is strikingly reminiscent of taxadiene, a biosynthetic intermediate for Taxol . The net biosynthesis for both involves geranylgeranyl diphosphate (GGDP) cyclization [9]. It is noteworthy that prior to isolation of phomactins, the only known related structure is cleomeolide, a diterpene from the herb Cleome viscosa [10] that remarkably resembles phomactin H. [Pg.185]

Figure 73. The carotenoid biosynthetic pathway. Enzymes are named according to the designation of their genes Ccs, capsanthin-capsorubin synthase CrtL-b, lycopene-b-cyclase CrtL-e, lycopene-e-cyclase CrtR-b, b-ring hydroxylase, CrtR-e, e-ring hydroxylase DMADP, dimethylallyl diphosphate GGDP, geranylgeranyl diphosphate Ggps, geranylgeranyl-diphosphate synthase IDP, isopentenyl diphosphate Ipi, IDP isomerase Pds, phytoene desaturase Psy, phytoene synthase Vde, violaxanthin de-epoxidase Zds, z-carotene desaturase Zep, zeaxanthin epoxidase. (From van den Berg and others 2000.)... Figure 73. The carotenoid biosynthetic pathway. Enzymes are named according to the designation of their genes Ccs, capsanthin-capsorubin synthase CrtL-b, lycopene-b-cyclase CrtL-e, lycopene-e-cyclase CrtR-b, b-ring hydroxylase, CrtR-e, e-ring hydroxylase DMADP, dimethylallyl diphosphate GGDP, geranylgeranyl diphosphate Ggps, geranylgeranyl-diphosphate synthase IDP, isopentenyl diphosphate Ipi, IDP isomerase Pds, phytoene desaturase Psy, phytoene synthase Vde, violaxanthin de-epoxidase Zds, z-carotene desaturase Zep, zeaxanthin epoxidase. (From van den Berg and others 2000.)...
Protein prenylation (also called isoprenylation) attaches a 15-carbon, farnesyl diphosphate or a 20-carbon geranylgeranyl diphosphate to the cysteine residue near the C termini of the target proteins (Overmeyer et al., 1998 Rodrfguez-Concepcion et al., 1999a). This reaction is conserved both in animals and plants. The functions of the target proteins include signal transduction, nuclear architecture, and vesicular transport. [Pg.306]

Fig. 11.3 Biosynthesis of the homoterpenes (a) DMNT (4,8-dimethyl-l,3,7-nonatriene) and (b) TMTT (4,8,12-trimethyltrideca-l,3,7,l 1-tetraene). (b) Two putative reaction mechanisms for the conversion of (ii,Zi)-geranyUinalool to TMTT catalyzed by a P450 enzyme activity are shown. FPP, farnesyl diphosphate GGPP, geranylgeranyl diphosphate... Fig. 11.3 Biosynthesis of the homoterpenes (a) DMNT (4,8-dimethyl-l,3,7-nonatriene) and (b) TMTT (4,8,12-trimethyltrideca-l,3,7,l 1-tetraene). (b) Two putative reaction mechanisms for the conversion of (ii,Zi)-geranyUinalool to TMTT catalyzed by a P450 enzyme activity are shown. FPP, farnesyl diphosphate GGPP, geranylgeranyl diphosphate...
Fig. 2. Schematic representation of paclitaxel biosynthesis. Dimethylallyl-diphosphate and isopentenyl-diphosphate are condensed through geranylgeranyl diphosphate synthase activity to render geranylgeranyl-diphosphate (GGPP). GGPP is converted into taxa-4(5), 11 (12)-diene in a reaction catalyzed by the taxane synthase (TS). A series of reactions catalyzed by cytochrome P450 monoxygenases lead to the production of a taxane intermediate that is further converted to baccatin III through enzymes-driven oxidation and oxetane ring formation. The side chain moiety of paclitaxel is derived from L-phenylalanine. Three consecutive arrows mean multiple steps. Ac, acetyl Bz, benzoyl. Fig. 2. Schematic representation of paclitaxel biosynthesis. Dimethylallyl-diphosphate and isopentenyl-diphosphate are condensed through geranylgeranyl diphosphate synthase activity to render geranylgeranyl-diphosphate (GGPP). GGPP is converted into taxa-4(5), 11 (12)-diene in a reaction catalyzed by the taxane synthase (TS). A series of reactions catalyzed by cytochrome P450 monoxygenases lead to the production of a taxane intermediate that is further converted to baccatin III through enzymes-driven oxidation and oxetane ring formation. The side chain moiety of paclitaxel is derived from L-phenylalanine. Three consecutive arrows mean multiple steps. Ac, acetyl Bz, benzoyl.
An exactly analogous process can then occur, in which geranyl diphosphate provides the allylic cation, and a further molecule of isopentenyl diphosphate adds on, giving farnesyl diphosphate this can subsequently yield geranylgeranyl diphosphate. [Pg.301]

The compounds geranyl diphosphate, farnesyl diphosphate, and geranylgeranyl diphosphate are biochemical precursors of monoterpenes, sesquiterpenes, and diterpenes respectively, and virtually all subsequent modifications of these precursors involve initial formation of an allylic cation through loss of diphosphate as the leaving group. [Pg.301]

This enzyme [EC 4.6.1.7] catalyzes the conversion of geranylgeranyl diphosphate to the antifungal diterpene... [Pg.114]

This enzyme [EC 2.5.1.29], also known as geranylgera-nyl-diphosphate synthase, catalyzes the condensation of transqrans-famesyl diphosphate and isopentenyl diphosphate to yield geranylgeranyl diphosphate and pyrophosphate. [Pg.278]

Phytoene synthase [EC 2.5.1.32] (also known as gera-nylgeranyl-diphosphate geranylgeranyltransferase and prephytoene-diphosphate synthase) catalyzes the reaction of two geranylgeranyl diphosphate to produce pyrophosphate (or, diphosphate) and prephytoene diphosphate. Isopentenyl pyrophosphate isomerase [EC 5.3.3.2] catalyzes the interconversion of isopentenyl diphosphate and dimethylallyl diphosphate. See also Geranylgeranyl Diphosphate Geranylgeranyltransferase... [Pg.562]

DIMETHYLALLYLTRANSTRANSFERASE Geranylgeranyl diphosphate synthase, FARNESYLTRANSTRANSFERASE Geranylgeranyltransferases,... [Pg.745]

Chain elongation during polymerization of prenyl units can be terminated in one of a number of ways. The pyrophosphate group may be hydrolyzed to a monophosphate or to a free alcohol. Alternatively, two polyprenyl compounds may join "head to head" to form a symmetric dimer. The C30 terpene squalene, the precursor to cholesterol, arises in this way from two molecules of famesyl diphosphate as does phy-toene, precursor of the Qo carotenoids, from E,E,E geranylgeranyl diphosphate. The phytanyl groups of archaebacterial lipids (p. 385) arise rather directly from geranylgeranyl diphosphate by transfer of the poly-... [Pg.1231]

The diterpenes arise from geranylgeranyl diphosphate (GGPP), which is formed by addition of a further IPP molecule to famesyl diphosphate in the same manner as described for the lower... [Pg.203]


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Geranylgeranyl

Geranylgeranyl diphosphate (GGPP

Geranylgeranyl diphosphate cyclization

Geranylgeranyl diphosphate synthase

Geranylgeranyl diphosphate synthase proteins

Phytoene from geranylgeranyl diphosphate

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