[en] Isoprenoids form an extensive group of natural products involved in a number of important biological processes. Their biosynthesis proceeds through sequential 1'-4 condensations of isopentenyl diphosphate (C(5)) with an allylic acceptor, the first of which is dimethylallyl diphosphate (C(5)). The reactions leading to the production of geranyl diphosphate (C(10)), farnesyl diphosphate (C(15)) and geranylgeranyl diphosphate (C(20)), which are the precursors of mono-, sesqui- and diterpenes, respectively, are catalyzed by a group of highly conserved enzymes known as short-chain isoprenyl diphosphate synthases, or prenyltransferases. In recent years, the sequences of many new prenyltransferases have become available, including those of several plant and animal geranyl diphosphate synthases, revealing novel mechanisms of product chain-length selectivity and an intricate evolutionary path from a putative common ancestor. Finally, there is considerable interest in designing inhibitors specific to short-chain prenyltransferases, for the purpose of developing new drugs or pesticides that target the isoprenoid biosynthetic pathway.
Disciplines :
Biochemistry, biophysics & molecular biology
Author, co-author :
Vandermoten, Sophie ; Université de Liège - ULiège > Gembloux Agro-Bio Tech > Gembloux Agro-Bio Tech
Haubruge, Eric ; Université de Liège - ULiège > Gembloux Agro-Bio Tech > Gembloux Agro-Bio Tech
Cusson, M.
Language :
English
Title :
New insights into short-chain prenyltransferases: structural features, evolutionary history and potential for selective inhibition.
Publication date :
2009
Journal title :
Cellular and Molecular Life Sciences
ISSN :
1420-682X
eISSN :
1420-9071
Publisher :
Springer Science & Business Media B.V., Basel, Switzerland
HV Thulasiram HK Erickson CD Poulter 2006 Chimeras of two isoprenoid synthases catalyze all four coupling reactions in isoprenoid biosynthesis Science 316 73 76 10.1126/science.1137786
Ogura K, Toyama T, Sagami H (1997) Polyprenyl diphopshate synthases. In: Bittman R (ed) Subcellular biochemistry, vol 28. Plenum, New York, pp 57-87
K Ogura T Koyama 1998 Enzymatic aspects of isoprenoid chain elongation Chem Rev 98 1263 1276 10.1021/cr9600464 1:CAS:528:DyaK1cXjtlygu7k%3D 11848932
TP Ko YK Chen H Robinson PC Tsai YG Gao APC Chen AHJ Wang PH Liang 2001 Mechanism of product chain length determination and the role of a flexible loop in Escherichia coli undecaprenyl-pyrophosphate synthase catalysis J Biol Chem 276 47474 47482 10.1074/jbc.M106747200 1:CAS:528:DC%2BD3MXpt1Gmtrc%3D 11581264
R Croteau PT Purkett 1989 Geranyl pyrophosphate synthase: characterization of the enzyme and evidence that this chain-length specific prenyltransferase is associated with monoterpene biosynthesis in sage (Salvia officinalis) Arch Biochem Biophys 271 524 535 10.1016/0003-9861(89)90304-4 1:CAS:528:DyaL1MXktlGnu7o%3D 2730002
CC Burke MR Wildung R Croteau 1999 Geranyl diphosphate synthase: cloning, expression, and characterization of this prenyltransferase as a heterodimer Proc Natl Acad Sci USA 96 13062 13067 10.1073/pnas.96.23.13062 1:CAS:528:DyaK1MXns1Gms7w%3D 10557273
CC Burke R Croteau 2002 Geranyl diphosphate synthase from Abies grandis: cDNA isolation, functional expression, and characterization Arch Biochem Biophys 405 130 136 10.1016/S0003-9861(02)00335-1 1:CAS:528:DC%2BD38XmtFShsLY%3D 12176066 (Pubitemid 35026174)
F Bouvier C Suire A d'Harlingue RA Backhaus B Camara 2000 Molecular cloning of geranyl diphosphate synthase and compartmentation of monoterpene synthesis in plant cells Plant J 24 241 252 10.1046/j.1365-313x.2000.00875.x 1:CAS:528:DC%2BD3cXosFSrtL4%3D 11069698 (Pubitemid 30820391)
D Tholl CM Kish I Orlova D Sherman J Gershenzon E Pichersky N Dudarevac 2004 Formation of monoterpenes in Antirrhinum majus and Clarkia breweri flowers involves heterodimeric geranyl diphosphate synthases Plant Cell 16 977 992 10.1105/tpc.020156 1:CAS:528:DC%2BD2cXjt1ynsb0%3D 15031409 (Pubitemid 38459217)
C Burke K Klettke R Croteau 2004 Heteromeric geranyl diphosphate synthase from mint: construction of a functional fusion protein and inhibition by bisphosphonate substrate analogs Arch Biochem Biophys 422 52 60 10.1016/j.abb.2003.12.003 1:CAS:528:DC%2BD2cXjtVamsg%3D%3D 14725857 (Pubitemid 38064310)
K Narita S Ohnuma T Nishino 1999 Protein design of geranyl diphosphate synthase: structural features that define the product specificities of prenyltransferases J Biochem (Tokyo) 126 566 571 1:CAS:528:DyaK1MXntVOitLw%3D
M Clastre B Bantignies G Feron E Soler C Ambid 1993 Purification and characterization of geranyl diphosphate synthase from Vitis vinifera L. Cv Muscat de Frontignan cell cultures Plant Physiol 102 205 211 1:CAS:528:DyaK3sXltFWrurw%3D 12231811
Schmidt, A, Gershenzon J (2008) Cloning and characterization of two different types of geranyl diphosphate synthases from Norway spruce (Picea abies) Phytochem. 69:49-57
AB Gilg JC Bearfield C Titigger WH Welch GJ Blomquist 2005 Isolation and functional expression of an animal geranyl diphosphate synthase, and its role in bark beetle pheromone biosynthesis Proc Natl Acad Sci USA 102 9760 9765 10.1073/pnas.0503277102 1:CAS:528:DC%2BD2MXmsFartb8%3D 15983375 (Pubitemid 40993642)
S Vandermoten B Charloteaux S Santini SE Sen C Béliveau M Vandenbol F Francis R Brasseur M Cusson E Haubruge 2008 Characterization of a novel aphid prenyltransferase displaying dual geranyl/farnesyl diphosphate synthase activity FEBS Lett 582 1928 1934 10.1016/j.febslet.2008.04.043 1:CAS:528:DC%2BD1cXms1Wiu7g%3D 18466770
MJ Lewis IM Prosser A Mohib LM Field 2008 Cloning and characterisation of a prenyltransferase from the aphid Myzus persicae with potential involvement in alarm pheromone biosynthesis Insect Mol Biol 17 437 443 10.1111/j.1365-2583. 2008.00815.x 1:CAS:528:DC%2BD1cXovFaqurY%3D 18651925
NL Eberhardt HC Rilling 1975 Prenyltransferase from Saccharomyces cerevisiae: purification to homogeneity and molecular properties J Biol Chem 250 863 866 1:CAS:528:DyaE2MXhtVyjs7k%3D 234442
BC Reed HC Rilling 1975 Crystallization and partial characterization of prenyltransferase from avian liver Biochemistry 14 50 54 10.1021/bi00672a009 1:CAS:528:DyaE2MXpsVKnsw%3D%3D 1109590
LS Yeh HC Rilling 1977 Purification and properties of pig liver prenyltransferase: interconvertible forms of the enzyme Arch Biochem Biophys 183 718 725 10.1016/0003-9861(77)90405-2 1:CAS:528:DyaE2sXlsVOks7s%3D 921283 (Pubitemid 8194587)
GF Barnard G Popjak 1981 Human liver prenyltransferase and its characterization Biochim Biophys Acta 661 87 99 1:CAS:528:DyaL3MXlt1yisLg%3D 7295734
P Hugueney B Camara 1990 Purification and characterization of farnesyl pyrophosphate synthase from Capsicum annuum FEBS Lett 273 235 238 10.1016/0014-5793(90)81093-4 1:CAS:528:DyaK3MXnslCntA%3D%3D 2172029 (Pubitemid 20362475)
CF Clarke RD Tanaka K Svenson M Wamsley AM Fogelman PA Edwards 1987 Molecular cloning and sequence of a cholesterol-repressible enzyme related to prenyltransferase in the isoprene biosynthetic pathway Mol Cell Biol 7 3138 3146 1:CAS:528:DyaL1cXltValug%3D%3D 3670308
DJ Wilkin SY Kutsunai PA Edwards 1990 Isolation and sequence of the human farnesyl pyrophosphate synthetase cDNA: coordinate regulation of the mRNAs for farnesyl pyrophosphate synthetase, 3-hydroxy-3-methylglutaryl coenzyme A reductase, and 3-hydroxy-3-methylglutaryl coenzyme A synthase by phorbol ester J Biol Chem 265 4607 4614 1:CAS:528:DyaK3cXitFWktb0%3D 1968462
T Koyama M Matsubara K Ogura 1985 Isoprenoid enzyme systems of silkworm. II: formation of the juvenile hormone skeletons by farnesyl pyrophosphate synthase II J Biochem 98 457 463 1:CAS:528:DyaL2MXmtV2ltrw%3D 4066650
M Castillo-Gracia F Couillaud 1999 Molecular cloning and tissue expression of an insect farnesyl diphosphate synthase Eur J Biochem 262 365 370 10.1046/j.1432-1327.1999.00385.x 1:CAS:528:DyaK1MXjvVGmsbg%3D 10336620 (Pubitemid 29266047)
K Kikuchi M Hirai T Shiotsuki 2001 Molecular cloning and tissue distribution of farnesyl pyrophosphate synthase from the silkworm J Insect Biotech Sericol 70 167 172 1:CAS:528:DC%2BD38XhtV2lsbo%3D
M Cusson C Béliveau SE Sen S Vandermoten RG Rutledge D Stewart F Francis E Haubruge P Rehse DJ Huggins APG Dowling GH Grant 2006 Characterization and tissue-specific expression of two lepidopteran farnesyl diphosphate synthase homologs: implications for the biosynthesis of ethyl-substituted juvenile hormones Proteins 65 742 758 10.1002/prot.21057 1:CAS:528: DC%2BD28XhtFWqt7fO 16972283 (Pubitemid 44583222)
SE Sen C Trobaugh C Beliveau T Richard M Cusson 2007 Cloning, expression and characterization of a dipteran farnesyl diphosphate synthase Insect Biochem Mol Biol 37 1198 1206 10.1016/j.ibmb.2007.07.011 1:CAS:528:DC%2BD2sXhtFehsrzO 17916506 (Pubitemid 47496218)
MS Anderson JG Yarger CL Burck CD Poulter 1989 Farnesyl diphosphate synthase: molecular cloning, sequence, and expression of an essential gene from Saccharomyces cerevisiae J Biol Chem 264 19176 19184 1:CAS:528: DyaK3cXhtFehurg%3D 2681213
N Cunillera M Arró D Delourme F Karst A Boronat A Ferrer 1996 Arabidopsis thaliana contains two differentially expressed farnesyl-diphosphate synthase genes J Biol Chem 271 7774 7780 10.1074/jbc.271.13.7774 1:CAS:528:DyaK28XhvFyktL4%3D 8631820 (Pubitemid 26107064)
Montalvetti A, Fernandez A, Sanders JM, Ghosh S, Van Brussel E, Oldfield E, Docampo R (2003) Farnesyl pyrophosphate synthase is an essential enzyme in Trypanosoma brucei: in vitro RNA interference and in vivo inhibition studies. J Biol Chem 278:17075-17083
H Hemmi M Noike T Nakayama T Nishino 2003 An alternative mechanism of product chain-length determination in type III geranylgeranyl diphosphate synthase Eur J Biochem 270 2186 2194 10.1046/j.1432-1033.2003.03583.x 1:CAS:528:DC%2BD3sXjvFOrtrc%3D 12752438 (Pubitemid 36605569)
K Wang S Ohnuma 1999 Chain-length determination mechanism of isoprenyl diphosphate synthases and implications for molecular evolution Trends Biochem Sci 24 445 451 10.1016/S0968-0004(99)01464-4 1:CAS:528:DC%2BD3cXkvFyruw%3D%3D 10542413 (Pubitemid 29528207)
T Kinjoh Y Kaneko K Itoyama K Mita K Hiruma T Shinoda 2007 Control of juvenile hormone biosynthesis in Bombyx mori: cloning of the enzymes in the mevalonate pathway and assessment of their developmental expression in the corpora allata Insect Biochem Mol Biol 37 808 818 10.1016/j.ibmb.2007.03.008 1:CAS:528:DC%2BD2sXnslWis7o%3D 17628279 (Pubitemid 47030925)
MC Schulbach PJ Brennan DC Crick 2000 Identification of a short (C15) chain Z-isoprenyl diphosphate synthase and a homologous long (C50) chain isoprenyl diphosphate synthase in Mycobacterium tuberculosis J Biol Chem 275 22876 22881 10.1074/jbc.M003194200 1:CAS:528:DC%2BD3cXltlGqsr0%3D 10816587 (Pubitemid 30646173)
MC Schulbach S Mahapatra M Macchia S Barontini C Papi F Minutolo S Bertini PJ Brennan DC Crick 2001 Purification, enzymatic characterization, and inhibition of the Z-farnesyl diphosphate synthase from Mycobacterium tuberculosis J Biol Chem 13 11624 11630 10.1074/jbc.M007168200
T Ambo M Noike H Kurokawa T Koyama 2008 Cloning and functional analysis of novel short-chain cis-prenyltransferases Biochem Biophys Res Commun 375 536 540 10.1016/j.bbrc.2008.08.057 1:CAS:528:DC%2BD1cXhtFCksLjK 18725204
C Sallaud D Rontein S Onillon F Jabès P Duffé C Giacalone S Thoraval C Escoffier G Herbette N Leonhardt M Causse A Tissier 2009 A novel pathway for sesquiterpene biosynthesis from Z,Z-farnesyl pyrophosphate in the wild tomato Solanum habrochaites Plant Cell 21 301 317 10.1105/tpc.107.057885 1:CAS:528:DC%2BD1MXlsFCit7c%3D 19155349
H Sagami T Korenaga K Ogura 1993 Geranylgeranyl diphosphate synthase catalyzing the single condensation between isopentenyl diphosphate and farnesyl diphosphate J Biochem 114 118 121 1:CAS:528:DyaK3sXmsVCjtLs%3D 8407863
Y Jiang P Proteau D Poulter S Ferro-Novick 1995 BTS1 encodes a geranylgeranyl diphosphate synthase in Saccharomyces cerevisiae J Biol Chem 270 21793 21799 10.1074/jbc.270.37.21793 1:CAS:528:DyaK2MXotFaisL0%3D 7665600
G Sandmann N Misawa M Wiedemann P Vittorioso A Carattoli G Morelli G Macino 1993 Functional identification of al-3 from Neurospora crassa as the gene for geranylgeranyl pyrophosphate synthase by complementation with crt genes, in vitro characterization of the gene product and mutant analysis J Photochem Photobiol 18 245 251 10.1016/1011-1344(93)80071-G 1:CAS:528:DyaK3sXkvVygtr4%3D (Pubitemid 23151460)
K Okada T Saito T Nakagawa M Kawamukai Y Kamiya 2000 Five geranylgeranyl diphosphate synthases expressed in different organs are localized into three subcellular compartments in Arabidopsis Plant Physiol 122 1045 1056 10.1104/pp.122.4.1045 1:CAS:528:DC%2BD3cXktFSqtbw%3D 10759500
T Kainou K Kawamura K Tanaka H Matsuda M Kawamukai 1999 Identification of the GGPS1 genes encoding geranylgeranyl diphosphate synthases from mouse and human Biochim Biophys Acta 1437 333 340 1:CAS:528:DyaK1MXitFantbs%3D 10101267
M Hojo T Matsumoto T Miura 2007 Cloning and expression of a geranylgeranyl diphosphate synthase gene: insights into the synthesis of termite defence secretion Insect Mol Biol 16 121 131 10.1111/j.1365-2583.2007.00709.x 1:CAS:528:DC%2BD2sXisFCnu78%3D 17257214 (Pubitemid 46174970)
S Ohnuma M Suzuki T Nishino 1994 Archaebacterial ether-linked lipid biosynthetic gene: expression cloning, sequencing, and characterization of geranylgeranyl-diphosphate synthase J Biol Chem 269 14792 14797 1:CAS:528:DyaK2cXlt1KntLk%3D 8182085
A Badillo J Steppuhn J Deruere B Camara M Kuntz 1995 Structure of a functional geranylgeranyl pyrophosphate synthase gene from Capsicum annum Plant Mol Biol 27 425 428 10.1007/BF00020196 1:CAS:528:DyaK2MXkt1KgsLw%3D 7888631
A Tachibana 1994 A novel prenyltransferase, farnesylgeranyl diphosphate synthase, from the haloalkaliphilic archaeon, Natronobacterium pharaonis FEBS Lett 341 291 294 10.1016/0014-5793(94)80475-3 1:CAS:528:DyaK2cXksFakurk%3D 8137956 (Pubitemid 24102700)
A Tachibana Y Yano S Otani N Nomura Y Sako M Taniguchi 2000 Novel prenyltransferase gene encoding farnesylgeranyl diphosphate synthase from a hyperthermophilic archaeon, Aeropyrum pernix: molecular evolution with alteration in product specificity FEBS J 267 321 328 1:CAS:528: DC%2BD3cXptl2mug%3D%3D
Y Ling Z Li K Miranda E Oldfield SNJ Moreno 2007 The farnesyl diphosphate/geranylgeranyl diphosphate synthase of Toxoplasma gondii is a bifunctional enzyme and a molecular target of bisphosphonates J Biol Chem 282 30804 30816 10.1074/jbc.M703178200 1:CAS:528:DC%2BD2sXhtFGgs7%2FM 17724033 (Pubitemid 350035188)
A Chen CD Poulter 1993 Purification and characterization of farnesyl diphosphate/geranylgeranyl diphosphate synthase: a thermostable bifunctional enzyme from Methanobacterium thermoautotrophicum J Biol Chem 268 11002 11007 1:CAS:528:DyaK3sXksVeqsb8%3D 8388380
M Cervantes-Cervantes CE Gallagher C Zhu ET Wurtzel 2006 Maize cDNAs expressed in endosperm encode functional farnesyl diphosphate synthase with geranylgeranyl diphosphate synthase activity Plant Physiol 140 220 231 10.1104/pp.106.077008 (Pubitemid 43956195)
SD Copley 2003 Enzymes with extra talents: moonlighting functions and catalytic promiscuity Curr Opin Chem Biol 7 265 272 10.1016/S1367-5931(03)00032- 2 1:CAS:528:DC%2BD3sXjtVKgsb0%3D 12714060 (Pubitemid 36514958)
Koyama T, Ogura K (1999) Isopentenyl diphosphate isomerase and prenyltransferases. In: Barton D, Nakanishi K (eds) Comprehensive natural products chemistry, vol 2. Elsevier, Oxford, pp 69-96
JW Cornforth RH Cornforth C Donninger G Popják 1966 Studies on the biosynthesis of cholesterol XIX: steric course of hydrogen eliminations and of C-C bond formations in squalene biosynthesis Proc R Soc Lond B 163 492 514 10.1098/rspb.1966.0004 1:STN:280:DyaF28%2Fot1OmsQ%3D%3D 4379291
LC Tarshis M Yan CD Poulter JC Sacchettini 1994 Crystal structure of recombinant farnesyl diphosphate synthase at 2.6 resolution Biochemistry 33 10871 10877 10.1021/bi00202a004 1:CAS:528:DyaK2cXlsFaisL8%3D 8086404
LC Tarshis PJ Proteau BA Kellogg JC Sacchettini CD Poulter 1996 Regulation of product chain length by isoprenyl diphosphate synthases Proc Natl Acad Sci USA 93 15018 15023 10.1073/pnas.93.26.15018 1:CAS:528:DyaK2sXmslOl 8986756 (Pubitemid 27009544)
DJ Hosfield Y Zhang DR Dougan A Broun LW Tari RV Swanson J Finn 2004 Structural basis for bisphosphonate-mediated inhibition of isoprenoid biosynthesis J Biol Chem 279 8526 8529 10.1074/jbc.C300511200 1:CAS:528:DC%2BD2cXhs1Onsbk%3D 14672944 (Pubitemid 38295905)
Gabelli S.B, McLellan J.S, Montalvetti A, Oldfield E, Docampo R, Amzel LM (2005) Structure and mechanism of the farnesyl diphosphate. Synthase from Trypanosoma cruzi: implications for drug design. Proteins 62:80-88
KL Kavanagh K Guo JE Dunford X Wu S Knapp FH Ebetino MJ Rogers RGG Russe U Oppermann 2006 The molecular mechanism of nitrogen-containing bisphosphonates as antiosteoporosis drugs Proc Natl Acad Sci USA 103 7829 7834 10.1073/pnas.0601643103 1:CAS:528:DC%2BD28XlsVGksL0%3D 16684881 (Pubitemid 43752866)
TH Chang RT Guo TP Ko AH Wang PH Liang 2006 Crystal structure of type-III geranylgeranyl pyrophosphate synthase from Saccharomyces cerevisiae and the mechanism of product chain length determination J Biol Chem 281 14991 15000 10.1074/jbc.M512886200 1:CAS:528:DC%2BD28XkslGqt7w%3D 16554305 (Pubitemid 43855203)
T Koyama Y Gotoh T Nishino 2000 Intersubunit location of the active site of farnesyl diphosphate synthase: reconstruction of active enzymes by hybrid-type heteromeric dimers of site-directed mutants Biochemistry 39 463 469 10.1021/bi991621b 1:CAS:528:DyaK1MXnvFCrtL4%3D 10631008 (Pubitemid 30056482)
KL Kavanagh JE Dunford G Bunkoczi RG Russell U Oppermann 2006 The crystal structure of human geranylgeranyl pyrophosphate synthase reveals a novel hexameric arrangement and inhibitory product binding J Biol Chem 281 22004 22012 10.1074/jbc.M602603200 1:CAS:528:DC%2BD28XnsVOmsLY%3D 16698791 (Pubitemid 44181904)
T Koyama S Obata M Osabe A Takeshita K Yokoyama M Uchida T Nishino K Ogura 1993 Thermostable farnesyl diphosphate synthase of Bacillus stearothermophilus: molecular cloning, sequence determination, overproduction, and purification J Biochem 113 355 363 1:CAS:528:DyaK3sXltFais7Y%3D 8486607
L Song CD Poulter 1994 Yeast farnesyl diphosphate synthase: site-directed mutagenesis of residues in highly conserved prenyltransferase domain I and II Proc Nat Acad Sci USA 91 3044 3048 10.1073/pnas.91.8.3044 1:CAS:528: DyaK2cXktVerur0%3D 8159703
H Fujii H Sagami T Koyama K Ogura S Seto T Baba CM Allen 1980 Variable product specificity of solanesyl pyrophosphate synthetase Biochem Biophys Res Commun 96 1648 1653 10.1016/0006-291X(80)91363-7 1:CAS:528:DyaL3MXis1Kqtg%3D%3D 7447947
S Ohnuma T Koyama K Ogura 1993 Alteration of the product specificities of prenyltransferases by metal ions Biochem Biophys Res Commun 192 407 412 10.1006/bbrc.1993.1430 1:CAS:528:DyaK3sXisFSnsb8%3D 8484753
S Ohnuma K Hirooka C Ohto T Nishino 1997 Conversion from archaeal geranylgeranyl diphosphate synthase to farnesyl diphosphate synthase: two amino acids before the first aspartate-rich motif solely determine eukaryotic farnesyl diphosphate synthase activity J Biol Chem 272 5192 5198 10.1074/jbc.272.1.580 1:CAS:528:DyaK2sXhsVaksr4%3D 9030588 (Pubitemid 27021197)
S Matsuoka H Sagami A Kurisaki K Ogura 1991 Variable product specificity of microsomal dehydrodolichyl diphosphate synthase from rat liver J Biol Chem 266 3464 3468 1:CAS:528:DyaK3MXhsF2luro%3D 1995611
S Fujiwara A Yamanaka K Hirooka A Kobayashi T Imanaka E Fukusaki 2004 Temperature-dependent modulation of farnesyl diphosphate/geranylgeranyl diphosphate synthase from hyperthermophilic archaea Biochem Biophys Res Commun 325 1066 1074 10.1016/j.bbrc.2004.10.129 1:CAS:528:DC%2BD2cXpslKnurw%3D 15541397 (Pubitemid 39487979)
S Ohnuma T Nakazawa H Hemmi AM Hallberg T Koyama K Ogura T Nishino 1996 Conversion from farnesyl diphosphate synthase to geranylgeranyl diphosphate synthase by random chemical mutagenesis J Biol Chem 271 10087 10095 10.1074/jbc.271.17.10087 1:CAS:528:DyaK28XisFGqu7w%3D 8626566 (Pubitemid 26131568)
S Ohnuma K Narita T Nakazawa C Ishida Y Takeuchi C Ohto T Nishino 1996 A role of the amino acid residue located on the fifth position before the first aspartate-rich motif of farnesyl diphosphate synthase on determination of the final product J Biol Chem 271 30748 30754 10.1074/jbc.271.48.30748 1:CAS:528:DyaK28Xntlaktr8%3D 8940054 (Pubitemid 26404094)
SMS Fernandez BA Kellogg CD Poulter 2000 Farnesyl diphosphate synthase: altering the catalytic site to select for geranyl diphosphate activity Biochemistry 39 15316 15321 10.1021/bi0014305 1:CAS:528:DC%2BD3cXotVyhsr0%3D (Pubitemid 32002758)
SE Sen M Cusson C Trobaugh C Béliveau T Richard W Graham A Mimms G Roberts 2007 Purification, properties and heteromeric association of type-1 and type-2 lepidopteran farnesyl diphosphate synthases Insect Biochem Mol Biol 37 819 828 10.1016/j.ibmb.2007.05.012 1:CAS:528:DC%2BD2sXnslWis7s%3D 17628280 (Pubitemid 47039214)
C Burke R Croteau 2002 Interaction with the small subunit of geranyl diphosphate synthase modifies the chain length specificity of geranylgeranyl diphosphate synthase to produce geranyl diphosphate J Biol Chem 277 3141 3149 10.1074/jbc.M105900200 1:CAS:528:DC%2BD38XhtVaksrc%3D 11733504 (Pubitemid 34953175)
A Chen PA Kroon CD Poulter 1994 Isoprenyl diphosphate synthases: protein sequence comparisons, a phylogenetic tree, and predictions of secondary structure Protein Sci 3 600 607 10.1002/pro.5560030816 1:CAS:528:DyaK2MXnvFal 8003978
T Dagan Y Artzy-Randrup W Martin 2008 Modular networks and cumulative impact of lateral transfer in prokaryote genome evolution Proc Natl Acad Sci USA 105 10039 10044 10.1073/pnas.0800679105 1:CAS:528:DC%2BD1cXptFGqur0%3D 18632554
F Cheng E Oldfield 2004 Inhibition of isoprene biosynthesis pathway enzymes by phosphonates, bisphosphonates, and diphosphates J Med Chem 47 5149 5158 10.1021/jm040036s 1:CAS:528:DC%2BD2cXntlOjtL0%3D 15456258 (Pubitemid 39314912)
JE Dunford K Thompson FP Coxon SP Luckman FM Hahn CD Poulter FH Ebetino MJ Rogers 2001 Structure-activity relationships for inhibition of farnesyl diphosphate synthase in vitro and inhibition of bone resorption in vivo by nitrogen-containing bisphosphonates J Pharmacol Exp Ther 296 235 242 1:CAS:528:DC%2BD3MXoslaluw%3D%3D 11160603
K Thompson JE Dunford FH Ebetino MJ Rogers 2002 Identification of a bisphosphonate that inhibits isopentenyl diphosphate isomerase and farnesyl diphosphate synthase Biochem Biophys Res Commun 290 869 873 10.1006/bbrc.2001. 6289 1:CAS:528:DC%2BD38XislartQ%3D%3D 11785983 (Pubitemid 34687524)
JD Bergstrom RG Bostedor PJ Masarachia AA Reszka G Rodan 2000 Alendronate is a specific, nanomolar inhibitor of farnesyl diphosphate synthase Arch Biochem Biophys 373 231 241 10.1006/abbi.1999.1502 1:CAS:528:DC%2BD3cXosVWl 10620343 (Pubitemid 30046509)
DE Hughes KR Wright HL Uy A Sasaki T Yoneda GD Roodman GR Mundy BF Boyce 1995 Bisphosphonates promote apoptosis in murine osteoclasts in vitro and in vivo J Bone Miner Res 10 1478 1487 1:CAS:528:DyaK2MXpsFGmsbo%3D 8686503
MJ Rogers DJ Watts RG Russell 1997 Overview of bisphosphonates Cancer 80 1652 1660 10.1002/(SICI)1097-0142(19971015)80:8+<1652::AID-CNCR15>3.0. CO;2-Z 1:CAS:528:DyaK2sXmvFyht7s%3D 9362432
GA Rodan 1998 Mechanisms of action of bisphosphonates Annu Rev Pharmacol Toxicol 38 375 388 10.1146/annurev.pharmtox.38.1.375 1:CAS:528: DyaK1cXivF2iurk%3D 9597160
DL Brown R Robbins 1999 Developments in the therapeutic applications of bisphosphonates J Clin Pharmacol 39 1 10
GA Rodan TJ Martin 2000 Therapeutic approaches to bone diseases Science 289 1508 1514 10.1126/science.289.5484.1508 1:CAS:528:DC%2BD3cXmt1Kgsb4%3D 10968781 (Pubitemid 30677465)
V Yardley AA Khan MB Martin TR Slifer FG Araujo SNJ Moreno R Docampo SL Croft E Oldfield 2002 In vivo activities of farnesyl pyrophosphate synthase inhibitors against Leishmania donovani and Toxoplasma gondii Antimicrob Agents Chemother 46 929 931 10.1128/AAC.46.3.929-931.2002 1:CAS:528: DC%2BD38XhsVKgsrk%3D 11850291 (Pubitemid 34157693)
N Rodriguez BN Bailey MB Martin E Oldfield JA Urbina R Docampo 2002 Radical cure of experimental cutaneous leishmaniasis by the bisphosphonate pamidronate J Infect Dis 186 138 140 10.1086/341074 1:CAS:528: DC%2BD38XlslSitr8%3D 12089677 (Pubitemid 34666929)
C Chen MP Hudock Y Zhang RT Guo R Cao JH No PH Liang TP Ko TH Chang SC Chang Y Song J Axelson A Kumar AH Wang E Oldfield 2008 Inhibition of geranylgeranyl diphosphate synthase by bisphosphonates: a crystallographic and computational investigation J Med Chem 51 5594 5607 10.1021/jm800325y 1:CAS:528:DC%2BD1cXhtVChs7zK
AL Chuiko MO Lozinsky I Jasicka-Misiak P Kafarski 1999 Herbicidal derivatives of aminomethylenebisphosphonic acid. Part IV: hydroxyalkylidenebisphosphonates, iminomethylenebisphosphonates and ureidomethylenebisphosphonates J Plant Growth Regul 18 171 174 10.1007/PL00007066 1:CAS:528:DC%2BD3cXhtF2htbg%3D 10688706
Palli SR, Cusson M (2007) Future insecticides targeting genes involved in the regulation of molting and metamorphosis. In: Ishaaya I, Nauen R, Horowitz AR (eds) Insecticide design using advanced technologies. Springer, Berlin, pp 105-134
K Tamura J Dudley M Nei S Kumar 2007 MEGA4: molecular evolutionary genetics analysis (MEGA) software version 4.0 Mol Biol Evol 24 1596 1599 10.1093/molbev/msm092 1:CAS:528:DC%2BD2sXpsVGrsL8%3D 17488738 (Pubitemid 47236692)
Hall BG (2008) Phylogenetic trees made easy: a how-to manual, 3rd edn, Sinauer Associates, Sunderland