Biosynthesis of Natural Rubber and Other Natural Polyisoprenoids
Part 2. Polyisoprenoids
Dr. Norimasa Ohya,
Prof.Dr. Tanetoshi Koyama,
Dr. Norimasa Ohya
- [email protected]
- +81-236-28-4583 | Fax: +81-236-28-4510
Yamagata University, Department of Material and Biological Chemistry, Faculty of Science, Koshirakawa-cho 1–4-12, Yamagata, Japan, 990–8560
Search for more papers by this authorProf.Dr. Tanetoshi Koyama
- [email protected]
- +81-22-217-5621 | Fax: +81-22-217-5620
Tohoku University, Institute of Multidisciplinary Research for Advanced Materials, Katahira 2–1-1, Aoba-ku, Sendai, Japan, 980–8577
Search for more papers by this authorDr. Norimasa Ohya,
Prof.Dr. Tanetoshi Koyama,
Dr. Norimasa Ohya
- [email protected]
- +81-236-28-4583 | Fax: +81-236-28-4510
Yamagata University, Department of Material and Biological Chemistry, Faculty of Science, Koshirakawa-cho 1–4-12, Yamagata, Japan, 990–8560
Search for more papers by this authorProf.Dr. Tanetoshi Koyama
- [email protected]
- +81-22-217-5621 | Fax: +81-22-217-5620
Tohoku University, Institute of Multidisciplinary Research for Advanced Materials, Katahira 2–1-1, Aoba-ku, Sendai, Japan, 980–8577
Search for more papers by this authorFirst published: 15 January 2005
Abstract
- Introduction
- Occurrence of Polyisoprene
- Chemical Properties of Rubber
- The Latex Vessel System
- Composition of Latex
- Molecular Weight of Rubber
- Historical Outline
- Rubber Precursors
- Rubber Formation on Rubber Particles
- Stereochemistry of Rubber Biosynthesis
- Initiator of Rubber Synthesis
- Biosynthesis Pathway in Hevea brasiliensis
- Formation of IPP
- Initiation of Rubber Molecules
- Chain-Elongation of Rubber
- 13C-NMR Study of Rubber Molecules
- Enzymes in Hevea brasiliensis
- Enzymes for the Formation of Mevalonic Acid
- Enzymes for the Formation of IPP
- Rubber Transferase
- Genetic Basis
- Rubber Biosynthesis-Related Proteins
- Rubber Elongation Factor (REF)
- 3-Hydroxy-3-Methylglutaryl Coenzyme A Reductase (HMGR)
- Isopentenyl Diphosphate Isomerase (IDPI)
- Farnesyl Diphosphate Synthase (FPS)
- Small Rubber Particle Protein (SRPP)
- Defense-Related Proteins
- Hevein
- Chitinase
- β-1,3-Glucanase
- Hever
- Latex Allergens
- Other Enzymes in Hevea
- Rubber Biosynthesis-Related Proteins
- Rubber Biosynthesis Pathways and Genes in Guayule and other Organisms
- Guayule Rubber Biosynthesis
- Rubber Synthesis in Indian Rubber Tree
- Rubber Synthesis in Fungi
- Production in Transgenic Plants and Recombinant Microorganisms
- Outlook and Perspectives
- Relevant Patents
- Stimulation of Rubber Yield and Rubber-Producing Plants
- Rubber Biosynthetic Genes and their Transformation
- Synthetic Use of Enzymes from H. brasiliensis
- Enzymes from Hevea and their DNA Sequences
- Acknowledgements
References
- Adiwilaga, K., Kush, A. (1996) Cloning and characterization of cDNA encoding farnesyl diphosphate synthase from rubber tree (Hevea brasiliensis), Plant Mol. Biol. 30, 935–946.
- Akasawa, A., Hsieh, L. S., Martin, B. M., Liu, T., Lin, Y. (1996) A novel acidic allergen, Hev b 5, in latex. Purification, cloning and characterization, J. Biol. Chem. 271, 25389–25393.
- Anderson, M. S., Yarger, J. G., Burck, C. L., Poulter, C. D. (1989) Farnesyl diphosphate synthetase: Molecular cloning, sequence, and expression of an essential gene from Saccharomyces cerevisiae, J. Biol. Chem. 264, 19176–19184.
- Anonymous (1977) Guayule: An alternative source of natural rubber, in: National Academy of Science, pp. 80. Washington D.C.
- Apfel, C. M., Takács, B., Fountoulakis, M., Stieger, M., Keck, W. (1999) Use of genomics to identify bacterial undecaprenyl pyrophosphate synthetase: Cloning, expression, and characterization of the essential uppS gene, J. Bacteriol. 181, 482–492.
- Archer, B. L. (1965) Site and mechanism of rubber biosynthesis from mevalonate, in: Proc. Nat. Rubb. Producers' Res. Assoc. Jubilee Conf. Cambridge, 1964, pp.101–112. (Mullins, L., Ed.) London: Maclaren.
- Archer, B. L. (1980) Polyisoprene in: Encyclopedia of Plant Physiology, vol. 8, Secondary Plant Products New Series, pp. 309–327. (Bell, E. A., Miller, L., Eds.) Berlin: Springer-Verlag.
- Archer, B. L., Audley, B. G. (1967) Biosynthesis of rubber, Adv. Enzymol. 29, 221–257.
- Archer, B. L., Audley, B. G. (1973) Rubber, gutta percha and chicle, in: Phytochemistry, ( F. F. Nord, L. P. Miller, Eds.) Vol. 2, pp. 310 –343. New York: Van Nostrand Reinhold.
- Archer, B. L., Audley, B. G. (1986) Rubber biosynthesis – Some new aspects, Proceedings of NSF sponsored workshops held at Texas A&M University, pp. 235–252.
- Archer, B. L., Audley, B. G. (1987) New aspects of rubber biosynthesis, Bot. J. Linn. Soc. 94, 181–196.
- Archer, B. L., Cockbain, E. G. (1969) Rubber transferase from Hevea brasiliensis latex, Methods Enzymol. 15, 476–480.
- Archer, B. L., Audley, B. G., Cookbain, E. G., McSweeney, G. P. (1963) The biosynthesis of rubber: Incorporation of mevalonate and isopentenyl pyrophosphate into rubber by Hevea brasiliensis-latex factions, Biochem. J. 89, 565–574.
- Archer, B. L., Barnard, E. G., Cockbain, E. G., Cornforth, J. W., Cornforth, R. H., Popják, G. (1965) The stereochemistry of rubber biosynthesis, Proc. Roy. Soc. Lond. Ser. B 163, 519–523.
- Archer, B. L., Ayrey, G., Cockbain, E. G., McSweeney, G. P. (1967) Incorporation of [1-14C]isopentenyl pyrophosphate into polyisoprene, Nature 189, 663–664.
- Archer, B. L., Audley, B. G., Bealing, F. J. (1982) Biosynthesis of rubber in Hevea brasiliensis, Plant. Rubber Int. 7, 109–111.
- Arokiaraj, P., Yeang, H. Y., Cheong, K. F., Hamzah, S., Jones, H., Coomber, S., Charlwood, B. V. (1998) CAMV 35S promoter directs β-glucuronidase expression in the laticiferous system of transgenic Hevea brasiliensis (rubber tree), Plant Cell Rep. 17, 621–625.
- Arreguin, B., Bonner, J., Wood, B. J. (1951) The mechanism of rubber formation in the guayule. Experiments with isotopic carbon, Arch. Biochem. Biophys. 31, 234–247.
- Attucci, S., Aitken, S. M., Ibrahim, R. K., Gulick, P. J. (1995) A cDNA encoding farnesyl pyrophosphate synthase in white lupin, Plant Physiol. 108, 835–836.
- Audley, B. G., Archer, B. L. (1988) Biosynthesis of rubber, in: Natural Rubber Science and Technology ( A. D. Roberts, Ed.) pp. 35. London: Oxford University Press.
- Backhaus, R. A. (1985) Rubber formation in plants, Israel J. Botany 34, 283–293.
- Backhaus, R. A., Cornish, K., Chen, S.-F., Huang, D.-S., Bess, V. H. (1991) Purification and characterization of an abundant rubber particle protein from guayule, Phytochemistry 30, 2493–2497.
- Backhaus, R. S., Walsh, S. (1983) The ontogeny of rubber formation in guayule, Parthenium argentatum Gray, Bot. Gaz. 144, 391–400.
- Bealing, F. J. (1969) Carbohydrate metabolism in Hevea latex: Availability and utilization of substrates, J. Rubb. Res. Int. Malaya 21, 445–455.
- Benedict, C. R., Madhavan, S., Greenblatt, G. A., Venkatachalam, K. V., Foster, M. A. (1989) The enzymatic synthesis of rubber polymer in Parthenium argentatum Gray, Plant Physiol. 92, 816–821.
- Boatman, S. G. (1966) Preliminary physiological studies on the promotion of latex flow by plant growth regulators, J. Rubb. Res. Inst. Malaya 19, 243–258.
- Booner, J. (1967) Rubber biogenesis, in: Biogenesis of Natural Compounds, 2nd ed. ( P. Bernfeld, Ed.) pp. 941. Oxford: Pergamon.
- Booner, J., Galston, A. (1947) Rubber formation in Plants, Bot. Rev. 13, 543–596.
- Bowler, W. W. (1953) Electrophoretic mobility study of fresh Hevea latex, Ind. Eng. Chem. 45, 1790–1794.
- Broekaert, W., Lee, H.-I., Kush, A., Chua, N.-H., Raikhel, N. (1990) Wound-induced accumulation of mRNA containing a hevein sequence in laticifers of rubber tree (Hevea brasiliensis), Proc. Natl. Acad. Sci. USA 87, 7633–7637.
- Burfield, D. R. (1976) Epoxy groups responsible for crosslinking in natural rubber, Nature 249, 29–30.
- Burfield, D. R. (1986) Storage hardening of natural rubber: An examination on current mechanistic proposal, J. Nat. Rubb. Res. 1, 202–208.
- Campos-Lopes, E., Neavez-Camacho, E., Maldonado-Garcia, R. (1978) Guayule, in: Reencuentra en el Desierto ( Ciqa Ed.) pp. 375. Mexico.
- Castillón, J., Cornish, K. (1999) Regulation of initiation and polymer molecular weight of cis-1,4-polyisoprene synthesized in vitro by particles isolated from Parthenium argentatum (Gray), Phytochemistry 51, 43–51.
- Chesterton, C. J., Kekwick, R. G. O. (1966) Evidence for the presence of Δ3-isopentenyl pyrophosphate isomerase activity from the formation of squalene in Hevea brasiliensis, Biochem. J. 100, 56–57.
- Chye, M. L., Cheung, K.-Y. (1995) β-1,3-Glucanase is highly-expressed in laticifers of Hevea brasiliensis, Plant Mol. Biol. 29, 397–402.
- Chye, M. L., Kush, A., Tan, C. T., Chua, N. H. (1991) Characterization of cDNA and genomic clones encoding 3-hydroxy-3-methylglutaryl-coenzyme A reductase from Hevea brasiliensis, Plant Mol. Biol. 16, 567–577.
- Chye, M. L., Tan, C. T., Chua, N. H. (1992) Three genes encode 3-hydroxy-3-methylglutaryl-coenzyme A reductase in Hevea brasiliensis: hmg1 and hmg3 are differentially expressed, Plant Mol. Biol. 19, 473–484.
- Clarke, C. F., Tanaka, R. D., Svenson, K., Wamsley, M., Fogelman, A. M., Edwards, P. A. (1987) Molecular cloning and sequence of a cholesterol-repressible enzyme related to prenyltransferase in the isoprene biosynthetic pathway, Mol. Cell. Biol. 7, 3138–3146.
- Cornish, K. (1993) The separate roles of plant cis and trans prenyl transferases in cis-1,4-polyisoprene biosynthesis, Eur. J. Biochem. 218, 267–271.
- Cornish, K., Backhaus, R. A. (1990) Rubber transferase activity in rubber particles of guayule, Phytochemistry 29, 3809–3813.
- Cornish, K., Siler, D. J. (1995) Effect of different allylic diphosphates on the initiation of new rubber molecules and on cis-1,4-polyisoprene biosynthesis in guayule (Parthenium argentatum Gray), J. Plant Physiol. 147, 301–305.
- Cornish, K., Siler, D. J. (1996) Characterization of cis-prenyl transferase activity localized in a buoyant fraction of rubber particles from Ficus elastica latex, Plant Physiol. Biochem. 34, 377–384.
- Cornish, K., Siler, D. J., Grosjean, O.-K., Goodman, N. (1993) Fundamental similarities in rubber particle architecture and function in three evolutionary divergent plant species, J. Nat. Rubb. Res. 8, 275–285.
- Cornish, K., Siler, D. J., Grosjean, O.-K. K. (1994) Immunoinhibition of rubber particle-bound cis-prenyl transferases in Ficus elastica and Parthenium argentatum, Phytochemistry 35, 1425–1428.
- Cornish, K., Castillón, J., Chapman, M. H. (1999) in: Biochemical Principles and Mechanisms of Biosynthesis and Biodegradation of Polymers ( A. Steinbüchel, Ed.) pp. 316–323. Weinheim: Wiley-VCH Verlag GmbH.
- Cunillera, N., Arró, M., Delourme, D., Karst, F., Boronat, A., Ferrer, A. (1996) Arabidopsis thaliana contains two differentially expressed farnesyl-diphosphate synthase genes, J. Biol. Chem. 271, 7774–7780.
- Czuppon, A. B., Chen, Z., Rennert, S., Engelke, T., Meyer, H. E., Heber, M., Baur, X. (1993) The rubber elongation factor of rubber trees (Hevea brasiliensis) is the major allergen in latex, J. Allergy Clin. Immunol. 92, 690–697.
- d‘Auzac, J. (1964) Demonstration of Hevea brasiliensis, Rev. Gen. Caoutchous 41, 1831–1834.
- Dennis, M. S., Light, D. R. (1989) Rubber elongation factor from Hevea brasiliensis: Identification, characterization, and role in rubber biosynthesis, J. Biol. Chem. 264, 18606–18617.
- Dennis, M. S., Henzel, W. J., Bell, J., Kohr, W., Light, D. R. (1989) Amino acid sequence of rubber elongation factor protein associated with rubber particles in Hevea latex, J. Biol. Chem. 264, 18618–18626.
- Dickenson, P. B. (1963) The ultrastructure of latex vessel of Hevea brasiliensis, in: The Chemistry and Physics of Rubber-like Substances ( L. Bateman, Ed.) pp. 41–51. London: Maclaren & Sons.
- Dickenson, P. B. (1969) Electron microscopic studies of the latex vessel system of Hevea brasiliensis, J. Rubb. Res. Inst. Malaya 21, 543–559.
- Eng, A. H., Tanaka, Y. (1994) trans-Isoprene units in natural rubber, Rubber Chem. Technol. 67, 159–168.
- Eng, A. H., Ejiri, S., Kawahara, S., Tanaka, Y. (1994) Structural characterization of natural rubber: Role of ester groups, J. Appl. Polym. Sci. Appl. Polym. Symp. 53, 5–14.
- Esau, K., (1965) Distribution of latex in the plant kingdom, in: Plant Anatomy, 2nd ed., pp. 318–319.
- Ericcson, J., Runquist, M., Thelin, A., Andersson, M., Chojnacki, T., Dallner, G. (1992) Distribution of prenyltransferases in rat tissues: Evidence for a cytosolic all-trans-geranylgeranyl diphosphate synthase, J. Biol. Chem. 268, 832–838.
- Fahn, A. (1979) Secretory Tissues in Plants, pp. 302. London: Academic Press.
- Gidrol, X., Chrestin, H., Tan, H.-L., Kush, A. (1994) Hevein, a lectin-like protein from Hevea brasiliensis (rubber tree) is involved in the coagulation of latex, J. Biol. Chem. 269, 9278–9283.
- Gomez, J. B., Moir, G. F. J. (1979) The ultracytology of latex vessels in Hevea brasiliensis, Malays. Rubb. Res. Dev. Board Monogr. Kuala Lumpur 4, 1–11.
- Goss, R. A., Benedict, C. R., Keithly, J. H., Nessler, C. L., Stipanovic, R. D. (1984) cis-Polyisoprene synthesis in guayule plants (Parthenium argentatum Gray) exposed to low, nonfreezing temperatures, Plant Physiol. 74, 534–537.
- Goyvaerts, E., Dennis, M., Light, D., Chua, N.-H. (1991) Cloning and sequencing of the cDNA encoding the rubber elongation factor of Hevea blasiliensis, Plant Physiol. 97, 317–321.
- Hager, T. A., MacArthur, A., McIntyre, D., Seeger, R. (1979) Chemistry and structure of natural rubbers, Rubber Chem. Technol. 52, 693–702.
- Harris, R. V., Kekwick, R. G. O. (1961) The incorporation of sodium [2-14C]acetate into rubber by the latex of Hevea brasiliensis, Biochem. J. 80, 10p.
- Hasma, H., Subramaniam, A. (1986) Composition of lipids in latex of Hevea brasiliensis clone PRIM501, J. Natl. Rubber Res. 1, 30–36.
- Hasslacher, M., Schall, M., Hayn, M., Griengl, H., Kohlwein, S. D., Schwab, H. (1996) Molecular cloning of the full-length cDNA of (S)-hydroxynitrile lyase from Hevea brasiliensis: Functional expression in Escherichia coli and Saccharomyces cerevisiae and identification of an active site residue, J. Biol. Chem. 271, 5884–5891.
- Hasslacher, M., Schall, M., Hayn, M., Bona, R., Rumbold, K., Luckl, J., Griengl, H., Kohlwein, S. D. (1997) High-level intracellular expression of hydroxynitrate lyase from the tropical rubber tree Hevea brasiliensis in microbial hosts, Protein Expr. Purif. 11, 61–71.
- Hepper, C. M., Audley, B. G. (1969) The biosynthesis of rubber from β-hydroxy-β-methylglutaryl-Coenzyme A in Hevea brasiliensis latex, Biochem. J. 114, 379–386.
- Ho, C. C., Subramaniam, A., Yong, W. M. (1975) Lipids associated with the particles in Hevea latex, Proc. Int. Rubb. Conf. 1975, Kuala Lumpur 2, 441–445.
- Jacob, J.-L., Sontag, N. (1974) Purification et etude de la phosphatase acid lutoidique du latex d‘Hevea brasiliensis, Biochimie 56, 1315–1322.
- Jekel, P. A., Bernard, J., Hartmann, H., Beintema, J. (1991) The primary structure of hevamine, an enzyme with lysozyme/chitinase activity from Hevea brasiliensis, Eur. J. Biochem. 200, 123–130.
- Kato, J., Fujisaki, S., Nakajima, K., Nishimura, Y., Sato, M., Nakano, A. (1999) The Escherichia coli homologue of yeast RER2, a key enzyme of dolichol synthesis, is essential for carrier lipid formation in bacterial cell wall synthesis, J. Bacteriol. 181, 2733–2738.
- Kekwick, R. G. O., Archer, B. L., Barnard, D., Higgins, G. M. C., McSweeney, G. P., Moore, C. G. (1959) Incorporation of DL-[2-14C]mevalonic acid lactone into polyisoprene, Nature, 184, 268–270.
- Kodama, S.
(1999)
Present situation and problem of rubber production in Malaysia, J. Soc. Rubb. Ind. (Japan) 72, 454–460.
10.2324/gomu.72.454 Google Scholar
- Kostyal, D. A., Hickey, V. L., Noti, J. D., Sussman, G. L., Beezhold, D. H. (1998) Cloning and characterization of a latex allergen (Hev b7): homology to patatin, a plant PL A2, Clin. Exp. Immunol. 112, 355–362.
- Koyama, T. (1999) Molecular analysis of prenyl chain elongating enzymes, Biosci. Biotechnol. Biochem. 63, 1671–1676.
- Koyama, T.,
Ogura, K.
(1999)
Isopentenyl diphosphate isomerase and prenyltransferases, in: Comprehensive Natural Products Chemistry ( D. Barton, K. Nakanishi, Eds.) vol. 2, pp. 69–96. Oxford: Elsevier Science Ltd.
10.1016/B978-0-08-091283-7.00037-0 Google Scholar
- Koyama, T., Obata, S., Osabe, M., Takeshita, A., Yokoyama, K., Uchida, M., Nishino, T., Ogura, K. (1993) Thermostable farnesyl diphosphate synthase of Bacillus stearothermophilus: Molecular cloning, sequence determination, overproduction, and purification, J. Biochem. 113, 355–363.
- Koyama, T., Wititsuwannakul, D., Asawatreratanakul, K., Wititsuwannakul, R., Ohya, N., Tanaka, Y., Ogura, K. (1996) Isopentenyl diphosphate isomerase in rubber latex, Phytochemistry 43, 769–772.
- Koyama, T., Shimizu, N., Ogura, K. (1999) Structure and function of polyisoprenoid chain elongation enzymes, in: Biochemical Principles and Mechanisms of Biosynthesis and Biodegradation of Polymers ( A. Steinbüchel, Ed.) pp. 308–315. Weinheim: Wiley-VCH Verlag GmbH.
- Kurihara, K., Kato, Y., Takei, Y., Shichiji, S. (1962) Production of rubber by microorganisms, Rep. Ferment. Res. Ind. (Japan) 22, 61–68.
- Kush, A., Goyvaerts, E., Chye, M.-L., Chua, N.-H. (1990) Laticifer-specific gene expression in Hevea blasiliensis (rubber tree), Proc. Natl. Acad. Sci. USA 87, 1787–1790.
- Leong, S. K., Leong, W., Yoon, P. K. (1982) Harvesting of shoots for rubber extraction in Hevea, J. Rubb. Res. Inst. Malaya 30, 117–122.
- Light, D. R., Dennis, M. S. (1989) Purification of a prenyltransferase that elongates cis-polyisoprene rubber from the latex of Hevea brasiliensis, J. Biol. Chem. 264, 18589–18597.
- Light, D. R., Lazarus, R. A., Dennis, M. S. (1989) Rubber elongation by farnesyl pyrophosphate synthases involve a novel switch in enzyme stereospecificity, J. Biol. Chem. 264, 18598–18607.
- Lu, X. J., Christensen, D. J., Poulter, C. D. (1992) Isopentenyl-diphosphate isomerase: irreversible inhibition by 3-methyl-3,4-epoxybutyldiphosphate, Biochemistry 31, 9955–9960.
- Lynen, F. (1967) Biosynthetic pathways from acetate to natural products, J. Pure Appl. Chem. 14, 137–167.
- Lynen, F. (1969) Biochemical problems of rubber synthesis, J. Rubb. Res. Inst. Malaya 21, 389–406.
- Lynen, F., Henning, U. (1960) The biological pathway to natural rubber, Angew. Chem. 72, 820–829.
- Madhavan, S., Benedict, C. R. (1984) Isopentenyl pyrophosphate cis-1,4-polyisoprenyl transferase from Guayule (Parthenium argentatum Gray), Plant Physiol. 75, 908–913.
- Madhavan, S., Greenblatt, G. A., Foster, M. A., Benedict, C. R. (1989) Stimulation of isopentenyl pyrophosphate incorporation into polyisoprene in extracts from guayule plants (Parthenium argentatam Gray) by low temperature and 2-(3,4-dichlorophenoxy)triethylamine, Plant Physiol. 89, 506–511.
- Martin, M. N. (1990) The latex of Hevea brasiliensis contains high levels of chitinases and chitinases/lysozymes, Plant Physiol. 95, 469–476.
- McMullen, A., McSweeney, G. P. (1966) Incorporation of isopentenyl pyrophosphate into purified rubber particles by a soluble latex-serum enzyme, Biochem. J. 101, 42–47.
- Miao, Z., Gaynor, J. J. (1993) Molecular cloning, characterization and expression of Mn-superoxide dismutase from the rubber tree (Hevea brasiliensis), Plant Mol. Biol. 23, 267–277.
- Muehlbacher, M., Poulter, C. D. (1997) Isopentenyl-diphosphate isomerase: inactivation of the enzyme with active-site-directed irreversible inhibitors and transit-state analogues, Biochemistry 27, 7315–7328.
- Ogura, K., Koyama, T. (1998) Enzymatic aspects of isoprenoid chain elongation, Chem. Rev. 98, 1263–1276.
- Oh, S. K., Kang, H., Shin, D. H., Yang, J., Chow, K.-S., Yeang, H. Y., Wagner, B., Breiteneder, H., Han, K.-H. (1999) Isolation, characterization, and functional analysis of a novel cDNA clone encoding a small rubber particle protein from Hevea brasiliensis, J. Biol. Chem. 274, 17132–17138.
- Ohya, N., Tanaka, Y. (1998) Structural characterization of rubber from Lactarius mushrooms; 1H-NMR analysis of terminal groups in the rubber chain, J. Rubb. Res. 1, 84–94.
- Ohya, N., Tanaka, Y., Ogura, K., Koyama, T. (1997) Isopentenyl diphosphate isomerase activity in Lactarius mushrooms, Phytochemistry 46, 1115–1118.
- Pan, Z., Durst, F., Werck-Reichhart, D., Gardner, H. W., Camara, B., Cornish, K., Backhaus, R. A. (1995) The major protein of guayule rubber particles is a cytochrome P450: Characterization based on cDNA cloning and spectroscopic analysis of the solubilized enzyme and its reaction products, J. Biol. Chem. 270, 8487–8494.
- Pan, Z., Herickhoff, L., Backhaus, R. A. (1996) Cloning, characterization, and heterologous expression of cDNAs for farnesyl diphosphate synthase from the guayule rubber plant reveals that this prenyltransferase occurs in rubber particles, Arch. Biochem. Biophys. 332, 196–204.
- Park, R. B., Bonner, J. (1958) Enzymatic synthesis of rubber from mevalonic acid, J. Biol. Chem. 233, 340–343.
- Paul, M. D. (1997) The biosynthesis of C5-C25 terpenoid compounds, Nat. Prod. Rep. 14, 111–144.
- Pendle, T. D., Swinyard, P. E. (1991) The particle size of natural rubber latex concentrates by photon correlation spectroscopy, J. Nat. Rubb. Res. 6, 1–11.
- Polhamus, L. G. (1962) Rubber – Botany, Production and Utilization, in: World Crops Series, pp. 43. London: Leonard Hill.
- Posh, A., Chen, Z., Dunn, M. J., Wheeler, C. H., Petersen, A., Leubner-Metzger, G., Baur, X. (1997a) Latex allergen database, Electrophoresis 18, 2803–2810.
- Posh, A., Chen, Z., Wheeler, C., Dunn, M. J., Raulf-Heimsoth, M., Baur, X. (1997b) Characterization and identification of latex allergens by two-dimensional electrophoresis and protein microsequencing, J. Allergy Clin. Immunol. 99, 385–395.
- Pujarniscle, S. (1968) Caractere lysosomal des lutoides du latex d‘Hevea brasiliensis, Physiol. Veg. 6, 27–46.
- Rabinowotz, J. L., Teas, H. J. (1961) Biosynthesis of rubber from Hevea, Proc. Nat. Rubb. Conf., Kuala Lumpur, 1960, 777–786.
- Rahaman, W. A. (1994) Natural rubber as a green comodity, Rubber Devel. 47, 12–16.
- Rohmer, M., Seemann, M., Grosdemange-Billiard, C. (2001) Biosynthetic Routes to the Building Blocks of Isoprenoids, Chapter 3 of this Volume.
- Rozeboom, H. J., Budiani, A., Beintema, J. J., Dijkstra, B. W. (1990) Crystallization of hevamine, an enzyme with lysozyme/chitinase activity from Hevea brasiliensis latex, J. Mol. Biol. 212, 441–443.
- Sato, M., Sato, K., Nishimura, S., Hirata, A., Kato, J., Nakano, A. (1999) The yeast RER2 gene, identified by endoplasmic reticulum protein localization mutations, encodes cis-prenyltransferase, a key enzyme in dolichol synthesis, Mol. Cell. Biol. 19, 471–483.
- Schoon, T. G. F., van der Bie, G. J. (1955) Particle size distribution in brominated Hevea latices, J. Polymer. Sci. 16, 63–88.
- Shimizu, N., Koyama, T., Ogura, K. (1998) Molecular cloning, expression, and purification of undecaprenyl diphosphate synthase: No sequence similarity between E- and Z-prenyl diphosphate synthases, J. Biol. Chem. 273, 19476–19481.
- Siler, D. J., Cornish, K. (1993) A protein from Ficus elastica rubber particles is related to proteins from Hevea brasiliensis and Parthenium argentatum, Phytochemistry 32, 1097–1102.
- Siler, D. J., Cornish, K. (1994) Identification of Parthenium argentatum rubber particle proteins immunoprecipitated by an antibody that specifically inhibits rubber transferase activity, Phytochemistry 36, 623–627.
- Silver, G. M., Fall, R. (1995) Characterization of aspen isoprene synthase, an enzyme responsible for leaf isoprene emission to the atmosphere, J. Biol. Chem. 270, 13010–13016.
- Sivasubramaniam, S., Vanniasingham, V. M., Tan, C.-T., Chua, N.-H. (1995) Characterization of HEVER, a novel stress-induced gene from Hevea brasiliensis, Plant Mol. Biol. 29, 173–178.
- Skilleter, D. N., Williamson, I. P., Kekwick, R. G. O. (1966) Phosphomevalonate kinase from Hevea brasiliensis latex, Biochem. J. 98, 27p.
- Slater, J. E., Vedvick, T., Arthur-Smith, A., Trybul, D. E., Kekwick, R. G. (1996) Identification, cloning, and sequence of a major allergen (Hev b5) from natural rubber latex (Hevea brasiliensis), J. Biol. Chem. 271, 25394–25399.
- Song, W.-C., Funk, C. D., Brash, A. R. (1993) Molecular cloning of an allene oxide synthase: A cytochrome P450 specialized for the metabolism of fatty acid hydroperoxides, Proc. Natl. Acad. Sci. USA 90, 8519–8523.
- Southorn, W. A. (1969) Physiology of Hevea (latex flow), J. Rubb. Res. Inst. Malaya 21, 494–512.
- Sowka, S., Wagner, S., Krebitz, M., Arija-Mad-Arit, S., Yusof, F., Kinaciyan, T., Brekler, R., Scheiner, O., Breiteneder, H. (1998) cDNA cloning of the 43-kDa latex allergen Hev b7 with sequence similarity to patatins and its expression in the yeast Pichia pastoris, Eur. J. Biochem. 255, 213–219.
- Stewart, W. D., Wachtel, W. L., Shipman, J. J., Yanko, J. A. (1955) Synthesis of rubber by fungi, Science 122, 1271–1272.
- Subramaniam, A. (1972) Gel-permeation chromatography of natural rubber, Rubb. Chem. Technol. 45, 346–348.
- Subramaniam, A. (1976) Molecular weight and other properties of natural rubber. A study of clonal variations, Proc. Int. Rubber Conf., Kuala Lumpur 1975 4, 3–27.
- Subramaniam, A. (1977) Estimation of aldehyde groups in natural rubber with 2,4-dinitrophenylhydrazine, J. Rubb. Res. Inst. Malaya 25, 61–68.
- Subramaniam, A. (1980) Molecular weight and molecular weight distribution of natural rubber, Rubb. Res. Inst. Malaya Technol. Bull. No. 4, 1–25.
- Suvachittanont, W., Wititsuwannakul, R (1995) 3-Hydroxy-3-methylglutaryl-coenzyme A synthase in Hevea brasiliensis, Phytochemistry 40, 757–761.
- Tanaka, Y. (1984) Structural characterization of naturally occurring cis polyisoprenes, in: NMR and Macromolecules, ACS Symposium Series (Randall, J. C., Ed.) No. 247, pp. 233–244. Washington D. C.: American Chemical Society.
- Tanaka, Y. (1985) Structural characterization of naturally occurring cis- and trans-polyisoprenes, Proc. Int. Rubb. Conf, Kyoto Japan 1985.
- Tanaka, Y. (1989) Structural Characterization of naturally occurring cis and trans polyisoprenes by 13C-NMR spectroscopy, J. Appl. Polym. Sci. Polym. Symp. 44, 1–9.
- Tanaka, Y., Sato, H. and Kageyu, A. (1983) Structure and biosynthesis mechanism of natural cis-polyisoprene from Goldenrod, Rubb. Chem. Tech. 56, 299–303.
- Tanaka, Y., Mori, M., Ute, K., Hatada, K. (1990) Structure and biosynthesis mechanism of rubber from fungi, Rubber Chem. Technol. 63, 1–7.
- Tanaka, Y., Kawahara, S., Eng, A. H., Takei, A., Ohya, N. (1994) Structure of cis-polyisoprene from Lactarius mushrooms, Acta Biochim. Pol. 41, 303–309.
- Tanaka, Y., Kawahara, S., Aik-Hwee, E., Shiba, K., Ohya, N. (1995) Initiation of biosynthesis in cis polyisoprenes, Phytochemistry 39, 779–784.
- Tangpakdee, J., Tanaka, Y., Ogura, K., Koyama, T., Wittitsuwannakul, R., Wititsuwannakul, D., Asawatreratanakul, K. (1997a) Isopentenyl diphosphate isomerase and prenyl transferase activities in bottom fraction and C-serum from Hevea latex, Phytochemistry 45, 261–267.
- Tangpakdee, J., Tanaka, Y., Ogura, K., Koyama, T., Wittitsuwannakul, R., Wittitsuwannakul, D. (1997b) Rubber formation by fresh bottom fraction of Hevea latex, Phytochemistry 45, 269–274.
- Tangpakdee, J., Tanaka, Y., Ogura, K., Koyama, T., Wittitsuwannakul, R., Chareonthiphakorn, N. (1997c) Structure of in vitro synthesized rubber from fresh bottom fraction of Hevea latex, Phytochemistry 45, 275–281.
- Tata, S. J., Boyce, A. N., Archer, B. L., Audley, B. G. (1976) Lysozymes: Major components of the sedimentable phase of Hevea latex, J. Rubb. Res. Inst. Malaya 24, 233–236.
- Teas, H. J., Bandursky, R. (1956) The enzymatic synthesis of rubber, J. Am. Chem. Soc. 78, 3549–3550.
- Turjanmaa, K. (1994) Allergy to natural rubber latex: a growing problem, Ann. Med. 26, 297–300.
- Wagner, B., Krebitz, M., Buck, D., Niggemann, B., Yeang, H. Y., Han, K. H., Scheiner, O., Breiteneder, H. (1999) Cloning, expression, and characterization of recombinant Hev b3, a Hevea brasiliensis protein associated with latex allergy in patients with spina bifida, J. Allergy Clin. Immunol. 104, 1084–1092.
- Weber, T., Bach, T. J. (1994) 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, Biochim. Biophys. Acta 1211, 85–96.
- Williamson, I. P., Kekwick, R. G. O. (1965) The formation of 5-phospho-mevalonate by mevalonate kinase in Hevea brasiliensis latex, Biochem. J., 96, 862–871.
- Wititsuwannakul, R., Wititsuwannakul, D., Suwanmanee, P. (1990a) 3-Hydroxy-3-methylglutaryl coenzyme A reductase from the latex of Hevea brasiliensis, Phytochemistry 29, 1401–1403.
- Wititsuwannakul, R., Wititsuwannakul, D., Dumkong, S. (1990b) Hevea calmodulin: Regulation of the activity of latex of 3-hydroxy-3-methylglutaryl coenzyme A reductase, Phytochemistry 29, 1755–1758.
- Wititsuwannakul, D., Wititsuwannakul, R. (2001) Biochemistry of Natural Rubber and Structure of Latex, Chapter 6 of this volume.
- Yeang, H. Y., Cheong, K. F., Sunderasan, E., Hamzah, S., Chew, N. P., Hamid, S., Hamilton, R. G., Cardosa, M. J. (1996) The 14.6 kD rubber elongation factor (Hev b1) and 24 kD (Hev b3) rubber particle proteins are recognized by IgE from patients with spina bifida and latex allergy, J. Allergy Clin. Immunol. 98, 628–639.
Biopolymers Online: Biology • Chemistry • Biotechnology • Applications
Browse other articles of this reference work: