Biosynthesis of Natural Rubber and Other Natural Polyisoprenoids

Dr. Norimasa Ohya1, Prof. Dr. Tanetoshi Koyama2 1 Department of Material and Biological Chemistry, Faculty of Science, Yamagata University, Koshirakawa-cho 1 ± 4-12, Yamagata 990 ± 8560, Japan; Tel.:‡81-236-28-4583; Fax:‡81-236-28-4510; E-mail: ohya@sci.kj.yamagata-u.ac.jp 2 Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, Katahira 2 ± 1-1, Aoba-ku, Sendai 980 ± 8577, Japan; Tel.:‡81-22-217-5621; Fax:‡81-22-217-5620; E-mail: koyama@icrs.tohoku.ac.jp

[1]  A. Kush,et al.  Cloning and characterization of cDNA encoding farnesyl diphosphate synthase from rubber tree (Hevea brasiliensis) , 1996, Plant Molecular Biology.

[2]  M. Chye,et al.  β-1,3-Glucanase is highly-expressed in laticifers of Hevea brasiliensis , 1995, Plant Molecular Biology.

[3]  N. Chua,et al.  Characterisation of HEVER, a novel stress-induced gene from Hevea brasiliensis , 1995, Plant Molecular Biology.

[4]  Z. Miao,et al.  Molecular cloning, characterization and expression of Mn-superoxide dismutase from the rubber tree (Hevea brasiliensis) , 1993, Plant Molecular Biology.

[5]  N. Chua,et al.  Three genes encode 3-hydroxy-3-methylglutaryl-coenzyme A reductase in Hevea brasiliensis: hmg1 and hmg3 are differentially expressed , 1992, Plant Molecular Biology.

[6]  N. Chua,et al.  Characterization of cDNA and genomic clones encoding 3-hydroxy-3-methylglutaryl-coenzyme A reductase from Hevea brasiliensis , 1991, Plant Molecular Biology.

[7]  M. Rohmer,et al.  Biosynthetic Routes to the Building Blocks of Isoprenoids , 2001 .

[8]  B. Niggemann,et al.  Cloning, expression, and characterization of recombinant Hev b 3, a Hevea brasiliensis protein associated with latex allergy in patients with spina bifida. , 1999, The Journal of allergy and clinical immunology.

[9]  H. Breiteneder,et al.  Isolation, Characterization, and Functional Analysis of a Novel cDNA Clone Encoding a Small Rubber Particle Protein from Hevea brasiliensis * , 1999, The Journal of Biological Chemistry.

[10]  K. Cornish,et al.  Regulation of initiation and polymer molecular weightof cis-1,4-polyisoprene synthesized in vitro by particlesisolated from Parthenium argentatum (Gray) , 1999 .

[11]  A. Nakano,et al.  The Escherichia coli Homologue of Yeast Rer2, a Key Enzyme of Dolichol Synthesis, Is Essential for Carrier Lipid Formation in Bacterial Cell Wall Synthesis , 1999, Journal of bacteriology.

[12]  M. Fountoulakis,et al.  Use of Genomics To Identify Bacterial Undecaprenyl Pyrophosphate Synthetase: Cloning, Expression, and Characterization of the Essential uppS Gene , 1999, Journal of bacteriology.

[13]  A. Nakano,et al.  The Yeast RER2 Gene, Identified by Endoplasmic Reticulum Protein Localization Mutations, Encodescis-Prenyltransferase, a Key Enzyme in Dolichol Synthesis , 1999, Molecular and Cellular Biology.

[14]  T. Koyama,et al.  2.04 – Isopentenyl DiphosphateIsomerase and Prenyltransferases , 1999 .

[15]  T. Koyama Molecular analysis of prenyl chain elongating enzymes. , 1999, Bioscience, biotechnology, and biochemistry.

[16]  T. Koyama,et al.  Molecular Cloning, Expression, and Purification of Undecaprenyl Diphosphate Synthase , 1998, The Journal of Biological Chemistry.

[17]  S. Wagner,et al.  cDNA cloning of the 43-kDa latex allergen Hev b 7 with sequence similarity to patatins and its expression in the yeast Pichia pastoris. , 1998, European journal of biochemistry.

[18]  D. Beezhold,et al.  Cloning and characterization of a latex allergen (Hev b 7): homology to patatin, a plant PLA2 , 1998, Clinical and experimental immunology.

[19]  T. Koyama,et al.  Enzymatic Aspects of Isoprenoid Chain Elongation. , 1998, Chemical reviews.

[20]  H. Yeang,et al.  CaMV 35S promoter directs β-glucuronidase expression in the laticiferous system of transgenic Hevea brasiliensis (rubber tree) , 1998, Plant Cell Reports.

[21]  T. Koyama,et al.  Isopentenyl diphosphate isomerase activity in Lactarius mushrooms , 1997 .

[22]  K Rumbold,et al.  High-level intracellular expression of hydroxynitrile lyase from the tropical rubber tree Hevea brasiliensis in microbial hosts. , 1997, Protein expression and purification.

[23]  T. Koyama,et al.  Structure of in vitro synthesized rubber from fresh bottom fraction of Hevea latex , 1997 .

[24]  T. Koyama,et al.  Rubber formation by fresh bottom fraction of hevea latex , 1997 .

[25]  T. Koyama,et al.  Isopentenyl diphosphate isomerase and prenyl transferase activities in bottom fraction and c-serum from Hevea latex , 1997 .

[26]  M. Dunn,et al.  Characterization and identification of latex allergens by two-dimensional electrophoresis and protein microsequencing. , 1997, The Journal of allergy and clinical immunology.

[27]  A. Petersen,et al.  Latex allergen database , 1997, Electrophoresis.

[28]  T. Koyama,et al.  Isopentenyl diphosphate isomerase in rubber latex , 1996 .

[29]  T. Vedvick,et al.  Identification, Cloning, and Sequence of a Major Allergen (Hev b 5) from Natural Rubber Latex (Hevea brasiliensis)* , 1996, The Journal of Biological Chemistry.

[30]  B. Martin,et al.  A Novel Acidic Allergen, Hev b 5, in Latex , 1996, The Journal of Biological Chemistry.

[31]  H. Yeang,et al.  The 14.6 kd rubber elongation factor (Hev b 1) and 24 kd (Hev b 3) rubber particle proteins are recognized by IgE from patients with spina bifida and latex allergy. , 1996, The Journal of allergy and clinical immunology.

[32]  R. Backhaus,et al.  Cloning, characterization, and heterologous expression of cDNAs for farnesyl diphosphate synthase from the guayule rubber plant reveals that this prenyltransferase occurs in rubber particles. , 1996, Archives of biochemistry and biophysics.

[33]  F. Karst,et al.  Arabidopsis thaliana Contains Two Differentially Expressed Farnesyl-Diphosphate Synthase Genes (*) , 1996, The Journal of Biological Chemistry.

[34]  S. Kohlwein,et al.  Molecular Cloning of the Full-length cDNA of (S)-Hydroxynitrile Lyase from Hevea brasiliensis , 1996, The Journal of Biological Chemistry.

[35]  K. Cornish,et al.  Characterization of cis-prenyl transferase activity localised in a buoyant fraction of rubber particles from Ficus elastica latex , 1996 .

[36]  R. Wititsuwannakul,et al.  3-Hydroxy-3-methylglutaryl-coenzyme, a synthase in Hevea brasiliensis , 1995 .

[37]  K. Shiba,et al.  Initiation of biosynthesis in cis polyisoprenes , 1995 .

[38]  R. Fall,et al.  Characterization of Aspen Isoprene Synthase, an Enzyme Responsible for Leaf Isoprene Emission to the Atmosphere (*) , 1995, The Journal of Biological Chemistry.

[39]  S. Aitken,et al.  A cDNA Encoding Farnesyl Pyrophosphate Synthase in White Lupin , 1995, Plant physiology.

[40]  K. Cornish,et al.  The Major Protein of Guayule Rubber Particles Is a Cytochrome P450 , 1995, The Journal of Biological Chemistry.

[41]  K. Cornish,et al.  Effect of Different Allylic Diphosphates on the Initiation of New Rubber Molecules and on Cis-1,4-polyisoprene Biosynthesis in Guayule (Parthenium argentatum Gray) , 1995 .

[42]  K. Turjanmaa Allergy to natural rubber latex: a growing problem. , 1994, Annals of medicine.

[43]  K. Cornish,et al.  Identification of Parthenium argentatum rubber particle proteins immunoprecipitated by an antibody that specifically inhibits rubber transferase activity , 1994 .

[44]  K. Cornish,et al.  Immunoinhibition of rubber particle-bound cis-prenyl transferases in Ficus elastica and Parthenium argentatum , 1994 .

[45]  X. Gidrol,et al.  Hevein, a lectin-like protein from Hevea brasiliensis (rubber tree) is involved in the coagulation of latex. , 1994, The Journal of biological chemistry.

[46]  S. Kawahara,et al.  Trans-Isofrene Units in Natural Rubber , 1994 .

[47]  T. Weber,et al.  Conversion of acetyl-coenzyme A into 3-hydroxy-3-methylglutaryl-coenzyme A in radish seedlings. Evidence of a single monomeric protein catalyzing a FeII/quinone-stimulated double condensation reaction. , 1994, Biochimica et biophysica acta.

[48]  S. Kawahara,et al.  Structure of cis-polyisoprene from Lactarius mushrooms. , 1994, Acta biochimica Polonica.

[49]  X. Baur,et al.  The rubber elongation factor of rubber trees (Hevea brasiliensis) is the major allergen in latex. , 1993, The Journal of allergy and clinical immunology.

[50]  K. Cornish The separate roles of plant cis and trans prenyl transferases in cis-1,4-polyisoprene biosynthesis. , 1993, European journal of biochemistry.

[51]  A. Brash,et al.  Molecular cloning of an allene oxide synthase: a cytochrome P450 specialized for the metabolism of fatty acid hydroperoxides. , 1993, Proceedings of the National Academy of Sciences of the United States of America.

[52]  K. Cornish,et al.  A protein from Ficus elastica rubber particles is related to proteins from Hevea brasiliensis and Parthenium argentatum , 1993 .

[53]  T. Koyama,et al.  Thermostable farnesyl diphosphate synthase of Bacillus stearothermophilus: molecular cloning, sequence determination, overproduction, and purification. , 1993, Journal of biochemistry.

[54]  J. Ericsson,et al.  Distribution of prenyltransferases in rat tissues. Evidence for a cytosolic all-trans-geranylgeranyl diphosphate synthase. , 1993, The Journal of biological chemistry.

[55]  X. J. Lu,et al.  Isopentenyl-diphosphate isomerase: irreversible inhibition by 3-methyl-3,4-epoxybutyl diphosphate. , 1992, Biochemistry.

[56]  N. Chua,et al.  Cloning and Sequencing of the cDNA Encoding the Rubber Elongation Factor of Hevea brasiliensis. , 1991, Plant physiology.

[57]  P. Jekel,et al.  The primary structure of hevamine, an enzyme with lysozyme/chitinase activity from Hevea brasiliensis latex. , 1991, European journal of biochemistry.

[58]  M. Martin,et al.  The Latex of Hevea brasiliensis Contains High Levels of Both Chitinases and Chitinases/Lysozymes. , 1991, Plant physiology.

[59]  K. Cornish,et al.  Purification and characterization of an abundant rubber particle protein from guayule , 1991 .

[60]  N. Raikhel,et al.  Wound-induced accumulation of mRNA containing a hevein sequence in laticifers of rubber tree (Hevea brasiliensis). , 1990, Proceedings of the National Academy of Sciences of the United States of America.

[61]  B. Dijkstra,et al.  Crystallization of hevamine, an enzyme with lysozyme/chitinase activity from Hevea brasiliensis latex. , 1990, Journal of molecular biology.

[62]  K. Ute,et al.  Structure and Biosynthesis Mechanism of Rubber from Fungi , 1990 .

[63]  N. Chua,et al.  Laticifer-specific gene expression in Hevea brasiliensis (rubber tree). , 1990, Proceedings of the National Academy of Sciences of the United States of America.

[64]  M. A. Foster,et al.  The Enzymatic Synthesis of Rubber Polymer in Parthenium argentatum Gray. , 1990, Plant physiology.

[65]  K. Cornish,et al.  Rubber transferase activity in rubber particles of guayule. , 1990 .

[66]  D. Wititsuwannakul,et al.  Hevea calmodulin: Regulation of the activity of latex 3-hydroxy-3-methylglutaryl coenzyme a reductase , 1990 .

[67]  C. Poulter,et al.  Farnesyl diphosphate synthetase. Molecular cloning, sequence, and expression of an essential gene from Saccharomyces cerevisiae. , 1989, The Journal of biological chemistry.

[68]  M. Dennis,et al.  Rubber elongation by farnesyl pyrophosphate synthases involves a novel switch in enzyme stereospecificity. , 1989, The Journal of biological chemistry.

[69]  M. Dennis,et al.  Purification of a prenyltransferase that elongates cis-polyisoprene rubber from the latex of Hevea brasiliensis. , 1989, The Journal of biological chemistry.

[70]  W. Kohr,et al.  Amino acid sequence of rubber elongation factor protein associated with rubber particles in Hevea latex. , 1989, The Journal of biological chemistry.

[71]  M. A. Foster,et al.  Stimulation of Isopentenyl Pyrophosphate Incorporation into Polyisoprene in Extracts from Guayule Plants (Parthenium argentatum Gray) by Low Temperature and 2-(3,4-Dichlorophenoxy) Triethylamine. , 1989, Plant physiology.

[72]  C. Poulter,et al.  Isopentenyl-diphosphate isomerase: inactivation of the enzyme with active-site-directed irreversible inhibitors and transition-state analogues. , 1988, Biochemistry.

[73]  K. Svenson,et al.  Molecular Cloning and Sequence of a Cholesterol-Repressible Enzyme Related to Prenyltransferase in the Isoprene Biosynthetic Pathway , 1987, Molecular and cellular biology.

[74]  B. L. Archer,et al.  New aspects of rubber biosynthesis , 1987 .

[75]  D. Wititsuwannakul,et al.  3-Hydroxy-3-methylglutaryl coenzyme A reductase from the latex of Hevea brasiliensis. , 1990 .

[76]  C. R. Benedict,et al.  Isopentenyl Pyrophosphate cis-1,4-Polyisoprenyl Transferase from Guayule (Parthenium argentatum Gray). , 1984, Plant physiology.

[77]  R. Stipanovic,et al.  cis-Polyisoprene Synthesis in Guayule Plants (Parthenium argentatum Gray) Exposed to Low, Nonfreezing Temperatures. , 1984, Plant physiology.

[78]  R. Backhaus,et al.  The Ontogeny of Rubber Formation in Guayule, Parthenium argentatum Gray , 1983, Botanical Gazette.

[79]  Hisaya Sato,et al.  Structure and Biosynthesis Mechanism of Natural Cis-Polyisoprene from Goldenrod , 1983 .

[80]  D. Mcintyre,et al.  Chemistry and Structure of Natural Rubbers , 1979 .

[81]  Nicole Sontag,et al.  Purification et tude de la phosphatase acide lutodique du latex d'Hevea brasiliensis , 1975 .

[82]  D. R. Burfield Epoxy groups responsible for crosslinking in natural rubber , 1974, Nature.

[83]  A. Subramaniam,et al.  Gel Permeation Chromatography of Natural Rubber , 1972 .

[84]  C. Hepper,et al.  The biosynthesis of rubber from β-hydroxy-β-methylglutaryl-coenzyme A in Hevea brasiliensis latex , 1969 .

[85]  E. Cockbain,et al.  [16] Rubber transferase from Hevea brasiliensis latex , 1969 .

[86]  F. Lynen Biosynthetic pathways from acetate to natural products , 1967, Pure and applied chemistry. Chimie pure et appliquee.

[87]  A. Mcmullen,et al.  The biosynthesis of rubber: Incorporation of isopentenyl pyrophosphate into purified rubber particles by a soluble latex serum enzyme. , 1966, The Biochemical journal.

[88]  I. P. Williamson,et al.  The formation of 5-phosphomevalonate by mevalonate kinase in Hevea brasiliensis latex. , 1965, The Biochemical journal.

[89]  E. Cockbain,et al.  The biosynthesis of rubber. Incorporation of mevalonate and isopentenyl pyrophosphate into rubber by Hevea brasiliensis-latex fractions. , 1963, The Biochemical journal.

[90]  E. Cockbain,et al.  Incorporation of [I-14C]-Isopentenyl Pyrophosphate into Polyisoprene , 1961, Nature.

[91]  F. Lynen,et al.  Über den biologischen Weg zum Naturkautschuk , 1960 .

[92]  R. Kekwick,et al.  Incorporation of DL-[2-14 C] Mevalonic Acid Lactone into Polyisoprene , 1959, Nature.

[93]  R. Park,et al.  Enzymatic synthesis of rubber from mevalonic acid. , 1958, Journal of Biological Chemistry.

[94]  H. Teas,et al.  THE ENZYMATIC SYNTHESIS OF RUBBER1 , 1956 .

[95]  J. Shipman,et al.  Synthesis of Rubber by Fungi. , 1955, Science.

[96]  T. Schoon,et al.  Particle size distribution in brominated Hevea latices , 1955 .

[97]  J. Bonner,et al.  Studies on the mechanism of rubber formation in the guayule. III. Experiments with isotopic carbon. , 1951, Archives of biochemistry and biophysics.