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Isoprenoid

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IdImageCOMMON NAMENAMEDATA No Lipid classINFORMANTSYMBOLFORMULAMOL.WT(average)Download cdx file / Mol format file BIOOGICAL ACTIVITY PHYSICAL AND CHEMICAL PROPERTIES SPECTRAL DATA CHROMATOGRAM DATA SOURCE CHEMICAL SYNTHESIS METABOLISM GENETIC INFORMATION NOTE REFERENCES
MELTING POINTBOILING POINTDENSITYREFRACTIVE INDEXOPTICAL ROTATIONSOLUBILITY UV SPECTRAIR SPECTRANMR SPECTRAMASS SPECTRAOTHER SPECTRA
1Tetrahydroxybacteriohopane/bacteriohopanetetrol 1,2,3,4-Tetrahydroxypentane-29-hopane IIP0112IsoprenoidYasutaka TaharaTHBH C35H62O4 546.864THBH may be localized in membranes , playing there the same role as sterols play in eukaryotes , as a result of their similar size , rigidity , and amphiphilic character . << Ref. 0005>> 181-182 Solubled in chloroform 3340,2920,2860,1360,1140,1110cm-1<< Ref. 0001>> 1H-NMR(CDCl3):d0.683(3H,s,18a-CH3),0.791(3h,s,4b-CH3),0.812(3h,s,4a-CH3),0.846(3h,s,10b-CH3),0.904(3h,d,J=6,22R-CH3),0.944(6H,s,8band 14aCH3),2.055(3H,s,CH3COO-),2.076(3h,s,CH3COO-),2.083(3H,s,CH3COO-)2.088(3H,s,CH3COO-),4.15(1H,dd,J35a,35=12,J35a,34=6,35Ha),4.39(1H,dd,J35a,35b=12,J35a,34=3,35-Hb), 5.03(1H,dt,J3233=9,J3231=3.5,32-H), 5.24(2H,m,33-H and 34-H)<< Ref. 0002>>13C-NMR(CDCl3):40.4(C-1),18.7(C-2),42.1(C-3),33.4(C-4),56.2(C-5),18.7(C-6),33.3(C-7),41.8(C-8),50.5(C-9),37.5(C-10),20.9(C-11),24.0(C-12),49.4(C-13),41.8(C-14),33.8(C-15),22.8(C-16),54.5(C-17),44.4(C-18),41.6(C-19),27.5(C-20),46.0(C-21),36.1(C-22),33.4(C-23),21.6(C-24),15.9(C-25),16.6(C-26),16.6(C-27),15.9(C-28),19.8(C-29),30.9(C-30),26.3(C-31),69.6(C-32),71.7(C-33),72.0(C-34),62.1(C-35),20.6(2,20.8,20.9(CH3CO-),169.6,169.8,170.2,170.5(CH3CO-)<< Ref. 0002>> EI-MS as a tetraacetate derivative:714(M+),493(M+-C16H29),369(C27H45+),191(C14H23+),137(C10H17+),95(C7H11+)<< Ref. 0001/0002>> TLC(Rf0.62 on silica gel H by chloroform/methanol/water,60:10:1,v/v)<< Ref. 0001>>GC(Retention time 28min as anacetylated derivative of 1-hydroxyethyl-29-hopane on a OV1/Gas Chrom Q column (2mm by 180cm) at a tenperature gradient from 180-300degC at 4degC/min<< Ref. 0003>> Cyanobasteria(Anabena variabilis,Calothrix sp.,Fischerella sp.,Nostoc muscorum B,Ascillatoria sp.,Scytonema sp.,Synechocystis sp.),Purple non-sulphur bacteria(Rhodomicrobium vannielii,Rhodoseudomonas acidphila,Rhodoseudomonas palustris,Rhodospirillum rubrum),Methylotrophs(Methylomonas albus,Methlomonas methanica,Methylocystis parvus,Methylosinus sporium,Methylosinus trichosporium,Methylococcus capsulatus),Gram-nagative chomoautotrophs(Nitrsomonas europaea),Gram-nagative chemoheterotrophs(Metylobacterium organophilum,Hyphomicrobiumsp.,Pseudomonas cepacia, Azotobacter chroococcum,Azotobacter vinelandii,Zymomonas mobilis),Acetic acid bacteria(A.aceti,A.liquefaciens,A.xylininum,A.pasteurianus,A.lovaniensis,A.orleanensis,A.pasteurianus,A.peroxydans,Gluconobacter oxydans),Gram-positive bacteria(Bacillus acidocaldarius,Streptomyces chartreusis,Streptomyces sp.)<< Ref. 0004>> Tetrahydroxypentane side-chain of THBH could be a D-ribose derivative linked through the C-5 carbon atom to hopane-22(29)-ene , hopane skelton . << Ref. 0006/0007>> Gene of squalene cyclase catalyzing cyclization of squalene to form hopane-22(29)-ene has been cloned and sequenced . << Ref. 0008>> << Ref.0001 >> AUTHOR: Langworthy, T. A., and Mayberry, W. R. TITLE: A 1,2,3,4-tetrahydroxy pentane-substituted pentacyclic triterpene from Bacillus acidocaldarius PubMed ID:7303 JOURNAL: Biochim Biophys Acta. VOLUME: 431 PAGE: 570-577(1976)
<< Ref.0002 >> AUTHOR: Renoux, J. M., and Rohmer, M. TITLE: Prokaryotic triterpenoids. New bacteriohopanetetrol cyclitol ethers from the methylotrophic bacterium Methylobacterium organophilum PubMed ID:3928379 JOURNAL: Eur J Biochem. VOLUME: 151 PAGE: 405-410(1985)
<< Ref.0003 >> AUTHOR: Bringer,S.,Hartner,T.,Poralla,K. and Sahm,H. TITLE: Influence of ethanol on the hopanoid content and the fatty acid pattern in batch and continuous cultures of Zymomonas mobilis. JOURNAL: Arch.Microbiol. VOLUME: 140 PAGE: 312 -316 (1985)
<< Ref.0004 >> AUTHOR: Rohmer,M.,Bouvier-Nave,P. and Ourisson,G. TITLE: Distribution of hopanoids triterpenes in prokaryotes. JOURNAL: J.Gen.Microbiol. VOLUME: 130 PAGE: 1137 -1150 (1984)
<< Ref.0005 >> AUTHOR: Rohmer, M., Bouvier, P., and Ourisson, G. TITLE: Molecular evolution of biomembranes: structural equivalents and phylogenetic precursors of sterols PubMed ID:284408 JOURNAL: Proc Natl Acad Sci U S A. VOLUME: 76 PAGE: 847-851(1979)
<< Ref.0006 >> AUTHOR: Flesch, G., and Rohmer, M. TITLE: Prokaryotic hopanoids: the biosynthesis of the bacteriohopane skeleton. Formation of isoprenic units from two distinct acetate pools and a novel type of carbon/carbon linkage between a triterpene and D-ribose PubMed ID:3136017 JOURNAL: Eur J Biochem. VOLUME: 175 PAGE: 405-411(1988)
<< Ref.0007 >> AUTHOR: Rohmer,M., Sutter ,B. and Sahm,H. TITLE: Bacterial Sterol Surrogates. Biosynthesis of the side-chain of Bacteriohopanetetrol and of a carbocyclic pseudopentose from 13C-labelled glucose in Zymomonas mobilis. JOURNAL: J.Chem.Soc.,Chem.Commun. VOLUME: PAGE: 1471 - (1989)
<< Ref.0008 >> AUTHOR: Ochs, D., Kaletta, C., Entian, K. D., Beck-Sickinger, A., and Poralla, K. TITLE: Cloning, expression, and sequencing of squalene-hopene cyclase, a key enzyme in triterpenoid metabolism PubMed ID:1729216 JOURNAL: J Bacteriol. VOLUME: 174 PAGE: 298-302(1992)
2Isopentenyl diphosphate 3-Methyl-3-butenyl diphosphate IIP0001IsoprenoidHiroshi SagamiIPP C5H8O7P2 242.060Download ChemDraw structure dataThe compound is an active isoprene unit commonly occurring in various organisms. Procedures for the synthesis and purification of this compound, other 20 isoprenoid diphosphates and methanediphosphate analogues from the corresponding alcohols are found in << Ref. 0014>>. The synthesis of isoprenoid (phosphinylmethyl)phosphonates are described in << Ref. 0015>> . Negative ion fast atom bombardment mass spectrometry (FABMS) has been used to obtain mass spectra of the naturally occurring isoprenoid metabolites including isopentenyl diphosphate, dimethylallyl diphosphate, geranyl diphosphate, and farnesyl diphosphate, presqualene diphosphate, and of several synthetic analogs including methylene-bridged diphosphates, bisphosphates, and nitrogen-containing analogs.<< Ref. 0023>> The study of plant polyisoprenoid alcohols including polyprenols and dolichols has been reviewed in << Ref. 0024>>. << Ref.0014 >> AUTHOR: Davisson,V. J., Woodside,A. B., Neal, T. R., Stremler, K. E., Muehlbacher, M., and Poulter, C. D. TITLE: Phosphorylation of isoprenoid alcohols. JOURNAL: J. Org. Chem. VOLUME: 51 PAGE: 4768 -4779 (1986)
<< Ref.0015 >> AUTHOR: Biller, S. A. and Forster, C. TITLE: The synthesis of isoprenoid (phosphinylmethyl)phosphonates. JOURNAL: Tetrahedron VOLUME: 46 PAGE: 6645 -6658 (1990)
<< Ref.0023 >> AUTHOR: Davisson, V.J., Sharp, T.R., and Poulter, C.D. TITLE: Negative ion fast atom bombardment mass spectrometry of isoprenoid diphosphates and related analogs. JOURNAL: Bioorganic Chem. VOLUME: 16 PAGE: 111 -123 (1988)
<< Ref.0024 >> AUTHOR: Swiezewska, E., Sasak, W., Mankowski, T., Jankowski, W., Vogtman, T., Krajewska, I., Hertel, J., Skoczylas, E., and Chojnacki, T. TITLE: The search for plant polyprenols PubMed ID:7856395 JOURNAL: Acta Biochim Pol. VOLUME: 41 PAGE: 221-260(1994)
3Dimethylallyl diphosphate 3-Methyl-2-butenyl diphosphate IIP0002IsoprenoidHiroshi SagamiDMAPP C5H8O7P2 242.060Download ChemDraw structure data This compound can be synthesized from dimethylallyl alcohol << Ref. 0014>>. The steroisomer of isopentenyl diphosphate and the product formed by the action of isopentenyl diphosphate isomerase. The nucleotide sequence of isopentenyl diphosphate:dimethylallyl diphosphate isomerase (Saccharomyces cerevisiae) has been submitted to the GenBankTM/EMBL data bank with accession number J05090.<< Ref. 0010>> << Ref.0010 >> AUTHOR: Anderson, M. S., Muehlbacher, M., Street, I. P., Proffitt, J., and Poulter, C. D. TITLE: Isopentenyl diphosphate:dimethylallyl diphosphate isomerase. An improved purification of the enzyme and isolation of the gene from Saccharomyces cerevisiae PubMed ID:2681212 JOURNAL: J Biol Chem. VOLUME: 264 PAGE: 19169-19175(1989)
<< Ref.0014 >> AUTHOR: Davisson,V. J., Woodside,A. B., Neal, T. R., Stremler, K. E., Muehlbacher, M., and Poulter, C. D. TITLE: Phosphorylation of isoprenoid alcohols. JOURNAL: J. Org. Chem. VOLUME: 51 PAGE: 4768 -4779 (1986)
4Geranyl diphosphate, Geranyl pyrophosphate [2E]-3,7-Dimethyl-2,6-octadien-1-yl diphosphate IIP0003IsoprenoidYoshichika YoshiokaGOPP, GPP C10H20O7P2 314.209Download ChemDraw structure dataMetabolic labeling of rat liver slices with mevalonic acid revealed the accumulation of E,E,E-geranylgeranyl (di)phosphate as well as dolichyl (di)phosphate (C85 and C90) and dehydrodolichol (C85 and C90), but no accumulation of Z,E,E-geranylgeranyl (di)phosphate or E,E-farnesyl (di)phosphate was detected<< Ref. 0026>>. The compound can be synthesized from geraniol.<< Ref. 0014>> The product formed by the action of geranyl diphosphate synthase and the first intermediate product by the action of farnesyl diphosphate synthase from dimethylallyl diphosphate and isopentenyl diphosphate. The potential for feedback inhibition by isoprene intermediates in the isoprene biosynthetic pathway was investigated. The relative inhibitory capacity was as follows: GG-PP > F-PP > G-PP > FOH > dol-P. GOH and dolichol were not inhibitors<< Ref. 0039>>. << Ref.0014 >> AUTHOR: Davisson,V. J., Woodside,A. B., Neal, T. R., Stremler, K. E., Muehlbacher, M., and Poulter, C. D. TITLE: Phosphorylation of isoprenoid alcohols. JOURNAL: J. Org. Chem. VOLUME: 51 PAGE: 4768 -4779 (1986)
<< Ref.0026 >> AUTHOR: Sagami, H., Matsuoka, S., and Ogura, K. TITLE: Formation of Z,E,E-geranylgeranyl diphosphate by rat liver microsomes PubMed ID:1995610 JOURNAL: J Biol Chem. VOLUME: 266 PAGE: 3458-3463(1991)
<< Ref.0039 >> AUTHOR: Hinson, D. D., Chambliss, K. L., Toth, M. J., Tanaka, R. D., and Gibson, K. M. TITLE: Post-translational regulation of mevalonate kinase by intermediates of the cholesterol and nonsterol isoprene biosynthetic pathways PubMed ID:9392419 JOURNAL: J Lipid Res. VOLUME: 38 PAGE: 2216-2223(1997)
5Farnesyl diphosphate, Farnesyl pyrophosphate [2E,6E]-3,7,11-Trimethyl-2,6,10-dodecatrien-1-yl diphosphate IIP0005IsoprenoidYoshichika YoshiokaFPP, FOPP C15H28O7P2 382.326Download ChemDraw structure dataRat liver microsomes catalyzed the formation of Z,E,E-geranylgeranyl diphosphate from farnesyl diphosphate and isopentenyl diphosphate in the presence of Triton X-100<< Ref. 0026>>. Metabolic labeling of rat liver slices with mevalonic acid revealed the accumulation of E,E,E-geranylgeranyl (di)phosphate as well as dolichyl (di)phosphate (C85 and C90) and dehydrodolichol (C85 and C90), but no accumulation of Z,E,E-geranylgeranyl (di)phosphate or E,E-farnesyl (di)phosphate was detected<< Ref. 0026>>. HMG-CoA reductase inhibitors induce apoptosis in mouse proximal tubular cells in primary culture. Geranylgeranylpyrophosphate and mevalonate completely reversed the effect of the inhibitors, while farnesylpyrophosphate partially reversed it and dolichol had no effect<< Ref. 0064>>. The compound can be synthesized from farnesol.<< Ref. 0014>> The rate of de novo synthesis of geranylgeranyl diphosphate from mevalonic acid is comparable to that of farnesyl diphosphate<< Ref. 0078>>. Geranylgeranyl diphosphate synthase catalyzing the single condensation between isopentenyl diphosphate and farnesyl diphosphate. The enzyme required Mg2+ and Mn2+ for maximum activity. Octylglucoside showed a stimulatory effect on the enzyme activity. Farnesyl diphosphate is the common intermediate at the branch point for the synthesis of geranylgeranylated proteins as well as cholesterol, ubiquinone, dolichol, and farnesylated proteins<< Ref. 0070>>. The uptake of F-PP and GG-PP was studied using primary cultures of chromaffin cells. Dolichylmonophosphate and isopentenylpyrophosphate promoted the uptake<< Ref. 0079>>. The potential for feedback inhibition by isoprene intermediates in the isoprene biosynthetic pathway was investigated. The relative inhibitory capasity were as follows: GG-PP > F-PP > G-PP > FOH > dol-P. GOH and dolichol were not inhibitors<< Ref. 0039>>. The crystal structure of recombinant farnesyl diphosphate synthase has been reported in << Ref. 0017>>.
The nucleotide sequence of yeast farnesyl diphosphate synthase has been reported in << Ref. 0019>>. Arabidopsis thaliana contains two differentially expressed farnesyl-diphosphate genes.<< Ref. 0038>>
<< Ref.0014 >> AUTHOR: Davisson,V. J., Woodside,A. B., Neal, T. R., Stremler, K. E., Muehlbacher, M., and Poulter, C. D. TITLE: Phosphorylation of isoprenoid alcohols. JOURNAL: J. Org. Chem. VOLUME: 51 PAGE: 4768 -4779 (1986)
<< Ref.0017 >> AUTHOR: Tarshis, L. C., Yan, M., Poulter, C. D., and Sacchettini, J. C. TITLE: Crystal structure of recombinant farnesyl diphosphate synthase at 2.6-A resolution PubMed ID:8086404 JOURNAL: Biochemistry. VOLUME: 33 PAGE: 10871-10877(1994)
<< Ref.0019 >> AUTHOR: Anderson, M. S., Yarger, J. G., Burck, C. L., and Poulter, C. D. TITLE: Farnesyl diphosphate synthetase. Molecular cloning, sequence, and expression of an essential gene from Saccharomyces cerevisiae PubMed ID:2681213 JOURNAL: J Biol Chem. VOLUME: 264 PAGE: 19176-19184(1989)
<< Ref.0026 >> AUTHOR: Sagami, H., Matsuoka, S., and Ogura, K. TITLE: Formation of Z,E,E-geranylgeranyl diphosphate by rat liver microsomes PubMed ID:1995610 JOURNAL: J Biol Chem. VOLUME: 266 PAGE: 3458-3463(1991)
<< Ref.0038 >> AUTHOR: de Ropp, J. S., and Troy, F. A. TITLE: 2H NMR investigation of the organization and dynamics of polyisoprenols in membranes PubMed ID:4066690 JOURNAL: J Biol Chem. VOLUME: 260 PAGE: 15669-15674(1985)
<< Ref.0039 >> AUTHOR: Hinson, D. D., Chambliss, K. L., Toth, M. J., Tanaka, R. D., and Gibson, K. M. TITLE: Post-translational regulation of mevalonate kinase by intermediates of the cholesterol and nonsterol isoprene biosynthetic pathways PubMed ID:9392419 JOURNAL: J Lipid Res. VOLUME: 38 PAGE: 2216-2223(1997)
<< Ref.0064 >> AUTHOR: Iimura, O., Vrtovsnik, F., Terzi, F., and Friedlander, G. TITLE: HMG-CoA reductase inhibitors induce apoptosis in mouse proximal tubular cells in primary culture PubMed ID:9328935 JOURNAL: Kidney Int. VOLUME: 52 PAGE: 962-972(1997)
<< Ref.0070 >> AUTHOR: Sagami, H., Korenaga, T., and Ogura, K. TITLE: Geranylgeranyl diphosphate synthase catalyzing the single condensation between isopentenyl diphosphate and farnesyl diphosphate PubMed ID:8407863 JOURNAL: J Biochem (Tokyo). VOLUME: 114 PAGE: 118-121(1993)
<< Ref.0078 >> AUTHOR: Sagami, H., Korenaga, T., Kurisaki, A., and Ogura, K. TITLE: Biosynthesis of prenyl diphosphates by cell-free extracts from mammalian tissues PubMed ID:8407862 JOURNAL: J Biochem (Tokyo). VOLUME: 114 PAGE: 112-117(1993)
<< Ref.0079 >> AUTHOR: Van Dessel, G., De Busser, H., and Lagrou, A. TITLE: Internalisation of short-chain isoprenyl diphosphates by chromaffin cells from bovine adrenal medulla PubMed ID:9299441 JOURNAL: Biochem Biophys Res Commun. VOLUME: 238 PAGE: 7-11(1997)
6Geranylgeranyl diphosphate, Geranylgeranyl pyrophosphate [2E,6E,10E]-3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraen-1-yl diphosphate IIP0006IsoprenoidYoshichika YoshiokaGGOPP, GGPP C20H36O7P2 450.443Download ChemDraw structure dataRat liver microsomes catalyzed the formation of Z,E,E-geranylgeranyl diphosphate from farnesyl diphosphate and isopentenyl diphosphate in the presence of Triton X-100<< Ref. 0026>>. HMG-CoA reductase inhibitors induce apoptosis in mouse proximal tubular cells in primary culture. Geranylgeranylpyrophosphate and mevalonate completely reversed the effect of the inhibitors, while farnesylpyrophosphate partially reversed it and dolichol had no effect<< Ref. 0064>>. The compound can be synthesized from geranylgeraniol .<< Ref. 0014>> The product formed by the action of geranylgeranyl diphosphate synthase. The rate of de novo synthesis of geranylgeranyl diphosphate from mevalonic acid is comparable to that of farnesyl diphosphate<< Ref. 0078>>. Geranylgeranyl diphosphate synthase catalyzing the single condensation between isopentenyl diphosphate and farnesyl diphosphate. The enzyme required Mg2+ and Mn2+ for maximum activity. Octylglucoside showed a stimulatory effect on the enzyme activity. Farnesyl diphosphate is the common intermediate at the branch point for the synthesis of geranylgeranylated proteins as well as cholesterol, ubiquinone, dolichol, and farnesylated proteins<< Ref. 0070>>. Purification and properties of geranylgeranyl-diphosphate synthase from bovine brain<< Ref. 0080>>. The uptake of F-PP and GG-PP was studied using primary cultures of chromaffin cells. Dolichylmonophosphate and isopentenylpyrophosphate promoted the uptake<< Ref. 0079>>. The potential for feedback inhibition by isoprene intermediates in the isoprene biosynthetic pathway was investigated. The relative inhibitory capasity were as follows: GG-PP > F-PP > G-PP > FOH > dol-P. GOH and dolichol were not inhibitors<< Ref. 0039>>. The nucleotide sequences of yeast Saccharomyces cerevisiae and human geranylgeranyl diphosphate synthase have been reported in << Ref. 0011>>and << Ref. 0016>>. African swine fever virus trans-polyprenyltransferase also catalyzes mainly geranylgeranyl diphosphate from farnesyl diphosphate and isopentenyl diphosphate. << Ref. 0013>> << Ref.0011 >> AUTHOR: Jiang, Y., Proteau, P., Poulter, D., and Ferro-Novick, S. TITLE: BTS1 encodes a geranylgeranyl diphosphate synthase in Saccharomyces cerevisiae PubMed ID:7665600 JOURNAL: J Biol Chem. VOLUME: 270 PAGE: 21793-21799(1995)
<< Ref.0013 >> AUTHOR: Alejo, A., Yanez, R. J., Rodriguez, J. M., Vinuela, E., and Salas, M. L. TITLE: African swine fever virus trans-prenyltransferase PubMed ID:9083080 JOURNAL: J Biol Chem. VOLUME: 272 PAGE: 9417-9423(1997)
<< Ref.0014 >> AUTHOR: Davisson,V. J., Woodside,A. B., Neal, T. R., Stremler, K. E., Muehlbacher, M., and Poulter, C. D. TITLE: Phosphorylation of isoprenoid alcohols. JOURNAL: J. Org. Chem. VOLUME: 51 PAGE: 4768 -4779 (1986)
<< Ref.0016 >> AUTHOR: Ericsson, J., Greene, J. M., Carter, K. C., Shell, B. K., Duan, D. R., Florence, C., and Edwards, P. A. TITLE: Human geranylgeranyl diphosphate synthase: isolation of the cDNA, chromosomal mapping and tissue expression PubMed ID:9741684 JOURNAL: J Lipid Res. VOLUME: 39 PAGE: 1731-1739(1998)
<< Ref.0026 >> AUTHOR: Sagami, H., Matsuoka, S., and Ogura, K. TITLE: Formation of Z,E,E-geranylgeranyl diphosphate by rat liver microsomes PubMed ID:1995610 JOURNAL: J Biol Chem. VOLUME: 266 PAGE: 3458-3463(1991)
<< Ref.0039 >> AUTHOR: Hinson, D. D., Chambliss, K. L., Toth, M. J., Tanaka, R. D., and Gibson, K. M. TITLE: Post-translational regulation of mevalonate kinase by intermediates of the cholesterol and nonsterol isoprene biosynthetic pathways PubMed ID:9392419 JOURNAL: J Lipid Res. VOLUME: 38 PAGE: 2216-2223(1997)
<< Ref.0064 >> AUTHOR: Iimura, O., Vrtovsnik, F., Terzi, F., and Friedlander, G. TITLE: HMG-CoA reductase inhibitors induce apoptosis in mouse proximal tubular cells in primary culture PubMed ID:9328935 JOURNAL: Kidney Int. VOLUME: 52 PAGE: 962-972(1997)
<< Ref.0070 >> AUTHOR: Sagami, H., Korenaga, T., and Ogura, K. TITLE: Geranylgeranyl diphosphate synthase catalyzing the single condensation between isopentenyl diphosphate and farnesyl diphosphate PubMed ID:8407863 JOURNAL: J Biochem (Tokyo). VOLUME: 114 PAGE: 118-121(1993)
<< Ref.0078 >> AUTHOR: Sagami, H., Korenaga, T., Kurisaki, A., and Ogura, K. TITLE: Biosynthesis of prenyl diphosphates by cell-free extracts from mammalian tissues PubMed ID:8407862 JOURNAL: J Biochem (Tokyo). VOLUME: 114 PAGE: 112-117(1993)
<< Ref.0079 >> AUTHOR: Van Dessel, G., De Busser, H., and Lagrou, A. TITLE: Internalisation of short-chain isoprenyl diphosphates by chromaffin cells from bovine adrenal medulla PubMed ID:9299441 JOURNAL: Biochem Biophys Res Commun. VOLUME: 238 PAGE: 7-11(1997)
<< Ref.0080 >> AUTHOR: Sagami, H., Morita, Y., and Ogura, K. TITLE: Purification and properties of geranylgeranyl-diphosphate synthase from bovine brain PubMed ID:8051156 JOURNAL: J Biol Chem. VOLUME: 269 PAGE: 20561-20566(1994)
7w-E,E,Z-Geranylgeranyl diphosphate, Cis-Geranylgeranyl diphosphate, geranylneryl diphosphate [2Z,6E,10E]-3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraen-1-yl diphosphate IIP0007IsoprenoidHiroshi Sagami C20H36O7P2 450.443Download ChemDraw structure data The compound can be synthesized from cis-geranylgeraniol .<< Ref. 0014>> The product formed by the action of cis-geranylgeranyl diphosphate synthase and the first product by the action of dehydrodolichul diphosphate synthase from farnesyl diphosphate and isopentenyl diphosphate.<< Ref. 0026>> << Ref.0014 >> AUTHOR: Davisson,V. J., Woodside,A. B., Neal, T. R., Stremler, K. E., Muehlbacher, M., and Poulter, C. D. TITLE: Phosphorylation of isoprenoid alcohols. JOURNAL: J. Org. Chem. VOLUME: 51 PAGE: 4768 -4779 (1986)
<< Ref.0026 >> AUTHOR: Sagami, H., Matsuoka, S., and Ogura, K. TITLE: Formation of Z,E,E-geranylgeranyl diphosphate by rat liver microsomes PubMed ID:1995610 JOURNAL: J Biol Chem. VOLUME: 266 PAGE: 3458-3463(1991)
8Phytyl diphosphate [2E]-3,7,11,15-Tetramethyl-2-hexadecen-1-yl diphosphate IIP0039IsoprenoidHiroshi Sagami C20H42O7P2 456.491Download ChemDraw structure data The compound is formed from geranylgeranyl diphosphate by the action of geranylgeranyl reductase. The nucleotide sequence of geranylgeranyl reductase is shown in << Ref. 0027>>. << Ref.0027 >> AUTHOR: Keller, Y., Bouvier, F., d'Harlingue, A., and Camara, B. TITLE: Metabolic compartmentation of plastid prenyllipid biosynthesis--evidence for the involvement of a multifunctional geranylgeranyl reductase PubMed ID:9492312 JOURNAL: Eur J Biochem. VOLUME: 251 PAGE: 413-417(1998)
9Geranylfarnesyl diphosphate [2E,6E,10E,14E]-3,7,11,15,19-Pentamethyl-2,6,10,14,18-eicosapentaen-1-yl diphosphate IIP0010IsoprenoidHiroshi SagamiGFPP C25H44O7P2 518.560Download ChemDraw structure data The product formed by the action of geranylfarnesyl diphosphate synthase.
10Hexaprenyl diphosphate, w-E,E,E,E,E-Hexaprenyl diphosphate, trans-Hexaprenyl diphosphate [2E,6E,10E,14E,18E]-3,7,11,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaen-1-yl diphosphate IIP0012IsoprenoidHiroshi Sagami C30H52O7P2 586.677Download ChemDraw structure data The product formed by the action of hexaprenyl diphosphate synthase.
11w-E,E,E,E,E,E-Heptaprenyl diphosphate, Heptaprenyl diphosphate [2E,6E,10E,14E,18E,22E]-3,7,11,15,19,23,27-Heptamethyl-2,6,10,14,18,22,26-octacosaheptaen-1-yl diphosphate IIP0014IsoprenoidHiroshi Sagami C35H60O7P2 654.794Download ChemDraw structure data The product formed by the action of heptaprenyl diphosphate synthase. Isoprene double bonds are trans except for w-isoprene double bond.
12Octaprenyl diphosphate, trans-Octaprenyl diphosphate [2E,6E,10E,14E,18E,22E,26E]-3,7,11,15,19,23,27,31-Octamethyl-2,6,10,14,18,22,26,30-dotriacontaoctaen-1-yl diphosphate IIP0016IsoprenoidHiroshi Sagami C40H68O7P2 722.911Download ChemDraw structure data The product formed by the action of octaprenyl diphosphate synthase. This compound contains trans isoprene double bonds except for w isoprene double bond. The amino acid sequence of Escherichia coli octaprenyl diphosphate synthase has (GenBank accession no. U18997) been reported in << Ref. 0018>>. << Ref.0018 >> AUTHOR: Okada, K., Minehira, M., Zhu, X., Suzuki, K., Nakagawa, T., Matsuda, H., and Kawamukai, M. TITLE: The ispB gene encoding octaprenyl diphosphate synthase is essential for growth of Escherichia coli PubMed ID:9139929 JOURNAL: J Bacteriol. VOLUME: 179 PAGE: 3058-3060(1997)
13Solanesyl diphosphate, Nonaprenyl diphosphate [2E,6E,10E,14E,18E,22E,26E,30E]-3,7,11,15,19,23,27,31,35-Nonamethyl-2,6,10,14,18,22,26,30,34-hexatriacontanonaen-1-yl diphosphate IIP0019IsoprenoidHiroshi Sagami C45H76O7P2 791.028Download ChemDraw structure data The product formed by the action of nonaprenyl diphosphate synthase. The amino acid sequence of solanesyl diphosphate synthase from Rhodobacter capsulatus << Ref. 0012>>. << Ref.0012 >> AUTHOR: Okada, K., Kamiya, Y., Zhu, X., Suzuki, K., Tanaka, K., Nakagawa, T., Matsuda, H., and Kawamukai, M. TITLE: Cloning of the sdsA gene encoding solanesyl diphosphate synthase from Rhodobacter capsulatus and its functional expression in Escherichia coli and Saccharomyces cerevisiae PubMed ID:9324242 JOURNAL: J Bacteriol. VOLUME: 179 PAGE: 5992-5998(1997)
14Decaprenyl diphosphate, trans-decaprenyl diphosphate [2E,6E,10E,14E,18E,22E,26E,30E,34E]-3,7,11,15,19,23,27,31,35,39-Decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaen-1-yl diphosphate IIP0023IsoprenoidHiroshi Sagami C50H84O7P2 859.145Download ChemDraw structure data The product formed by the action of decaprenyl diphosphate synthase.
15Undecaprenyl diphosphate, wt2c8-C55-prenyl diphosphate [2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,34E,38E]-3,7,11,15,19,23,27,31,35,39,43-Undecamethyl-2,6,10,14,18,22,26,30,34,38,42-tetratetracontaundecaen-1-yl diphosphate IIP0027IsoprenoidHiroshi Sagami C55H90O7P2 925.246Download ChemDraw structure data The compound is synthesized by the action of undecaprenyl diphosphate synthase. The nucleotide sequence of Micrococcus luteus undecaprenyl diphosphate synthase << Ref. 0020>>. << Ref.0020 >> AUTHOR: Shimizu, N., Koyama, T., and Ogura, K. TITLE: Molecular cloning, expression, and purification of undecaprenyl diphosphate synthase. No sequence similarity between E- and Z-prenyl diphosphate synthases PubMed ID:9677368 JOURNAL: J Biol Chem. VOLUME: 273 PAGE: 19476-19481(1998)
16Dolichyl-17 diphosphate, a-Dihydroheptadecaprenyl diphosphate [6Z,10Z,14Z,18Z,22Z,26Z,30Z,34Z,38Z,42Z,46Z,50Z,54Z,58E,62E]-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67-Heptadecamethyl-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66-octahexacontahexadecaen-1-yl diphosphate IIP0073IsoprenoidYoshichika YoshiokaDol-17-PP C85H142O7P2 1337.980Download ChemDraw structure dataCalf brain microsomes catalyze the enzymatic release of P from exogenous Dol-PP by a bacitracin-sensitive reaction<< Ref. 0102>>. Metabolic labeling of rat liver slices with mevalonic acid revealed the accumulation of E,E,E-geranylgeranyl (di)phosphate as well as dolichyl (di)phosphate (C85 and C90) and dehydrodolichol (C85 and C90), but no accumulation of Z,E,E-geranylgeranyl (di)phosphate or E,E-farnesyl (di)phosphate was detected<< Ref. 0026>>. The effects of TSH on dolichol-linked sugar pools and oligosaccharyltransferase activity in thyroid cells were investigated. TSH slightly increased the amount of dolichol-PP and acitivated the oligosaccharyltransferase<< Ref. 0072>>. << Ref.0026 >> AUTHOR: Sagami, H., Matsuoka, S., and Ogura, K. TITLE: Formation of Z,E,E-geranylgeranyl diphosphate by rat liver microsomes PubMed ID:1995610 JOURNAL: J Biol Chem. VOLUME: 266 PAGE: 3458-3463(1991)
<< Ref.0072 >> AUTHOR: Desruisseau, S., Valette, A., Franc, J. L., and Chabaud, O. TITLE: Thyrotropin controls dolichol-linked sugar pools and oligosaccharyltransferase activity in thyroid cells PubMed ID:8902853 JOURNAL: Mol Cell Endocrinol. VOLUME: 122 PAGE: 223-228(1996)
<< Ref.0102 >> AUTHOR: Scher, M. G., and Waechter, C. J. TITLE: Brain dolichyl pyrophosphate phosphatase. Solubilization, characterization, and differentiation from dolichyl monophosphate phosphatase activity PubMed ID:6094565 JOURNAL: J Biol Chem. VOLUME: 259 PAGE: 14580-14585(1984)
17Dolichyl-18 diphosphate, a-Dihydrooctadecaprenyl diphosphate [6Z,10Z,14Z,18Z,22Z,26Z,30Z,34Z,38Z,42Z,46Z,50Z,54Z,58Z,62E,66E]-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71-Octadecamethyl-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70-doheptacontaheptadecaen-1-yl diphosphate IIP0074IsoprenoidYoshichika YoshiokaDol-18-PP C90H150O7P2 1406.097Download ChemDraw structure dataMetabolic labeling of rat liver slices with mevalonic acid revealed the accumulation of E,E,E-geranylgeranyl (di)phosphate as well as dolichyl (di)phosphate (C85 and C90) and dehydrodolichol (C85 and C90), but no accumulation of Z,E,E-geranylgeranyl (di)phosphate or E,E-farnesyl (di)phosphate was detected<< Ref. 0026>>.