CrossRef enabled

PAC Archives

Archive →

Pure Appl. Chem., 1975, Vol. 41, No. 1-2, pp. 219-245

http://dx.doi.org/10.1351/pac197541010219

Stereochemical aspects of sesquiterpene biosynthesis

D. Arigoni

CrossRef Cited-by theme picture

CrossRef Cited-by Linking

  • Baer Philipp, Rabe Patrick, Citron Christian A., de Oliveira Mann Carina C., Kaufmann Norman, Groll Michael, Dickschat Jeroen S.: Hedycaryol Synthase in Complex with Nerolidol Reveals Terpene Cyclase Mechanism. ChemBioChem 2014, 15, 213. <http://dx.doi.org/10.1002/cbic.201300708>
  • Rabe Patrick, Dickschat Jeroen S.: Schnelle chemische Charakterisierung bakterieller Terpen- Synthasen. Angew. Chem. 2013, 125, 1855. <http://dx.doi.org/10.1002/ange.201209103>
  • Rabe Patrick, Dickschat Jeroen S.: Rapid Chemical Characterization of Bacterial Terpene Synthases. Angew. Chem. Int. Ed. 2013, 52, 1810. <http://dx.doi.org/10.1002/anie.201209103>
  • Rabe Patrick, Citron Christian A., Dickschat Jeroen S.: Volatile Terpenes from Actinomycetes: A Biosynthetic Study Correlating Chemical Analyses to Genome Data. ChemBioChem 2013, 14, 2345. <http://dx.doi.org/10.1002/cbic.201300329>
  • Faraldos Juan A., Miller David J., González Verónica, Yoosuf-Aly Zulfa, Cascón Oscar, Li Amang, Allemann Rudolf K.: A 1,6-Ring Closure Mechanism for (+)-δ-Cadinene Synthase?. S J Am Chem Soc 2012, 134, 5900. <http://dx.doi.org/10.1021/ja211820p>
  • Miller David J., Allemann Rudolf K.: Sesquiterpene synthases: Passive catalysts or active players?. Natural Products Report 2012, 29, 60. <http://dx.doi.org/10.1039/c1np00060h>
  • Hu Yunfeng, Chou Wayne K.W., Hopson Russell, Cane David E.: Genome Mining in Streptomyces clavuligerus: Expression and Biochemical Characterization of Two New Cryptic Sesquiterpene Synthases. CHEM BIOL 2011, 18, 32. <http://dx.doi.org/10.1016/j.chembiol.2010.11.008>
  • Hong Young J., Tantillo Dean J.: The Taxadiene-Forming Carbocation Cascade. S J Am Chem Soc 2011, 133, 18249. <http://dx.doi.org/10.1021/ja2055929>
  • Boland Wilhelm, Garms Stefan: Induced volatiles of Medicago truncatula: molecular diversity and mechanistic aspects of a multiproduct sesquiterpene synthase from M. truncatula . Flavour Fragr J 2010, 25, 114. <http://dx.doi.org/10.1002/ffj.1979>
  • Hong Young J., Tantillo Dean J.: A tangled web—interconnecting pathways to amorphadiene and the amorphene sesquiterpenes. Chem Sci 2010, 1, 609. <http://dx.doi.org/10.1039/c0sc00333f>
  • Adio Adewale M.: Germacrenes A–E and related compounds: thermal, photochemical and acid induced transannular cyclizations. Tetrahedron 2009, 65, 1533. <http://dx.doi.org/10.1016/j.tet.2008.11.050>
  • KIMURA Makoto, TOKAI Takeshi, TAKAHASHI-ANDO Naoko, OHSATO Shuichi, FUJIMURA Makoto: Molecular and Genetic Studies of Fusarium Trichothecene Biosynthesis: Pathways, Genes, and Evolution. Biosci Biotechnol Biochem 2007, 71, 2105. <http://dx.doi.org/10.1271/bbb.70183>
  • Cane David E.: Brushes with sage. Archives of Biochemistry and Biophysics 2006, 448, 117. <http://dx.doi.org/10.1016/j.abb.2005.08.023>
  • Eschenmoser Albert, Arigoni Duilio: Revisited after 50 Years: The ‘Stereochemical Interpretation of the Biogenetic Isoprene Rule for the Triterpenes’. HCA 2005, 88, 3011. <http://dx.doi.org/10.1002/hlca.200590245>
  • GinerCurrent address: Department of José-Luis, Rocchetti Stefano, Neunlist Serge, Rohmer Michel, Arigoni Duilio: Detection of 1,2-hydride shifts in the formation of euph-7-ene by the squalene–tetrahymanol cyclase of Tetrahymena pyriformis. Chem Commun 2005, 3089. <http://dx.doi.org/10.1039/b504300j>
  • Kerber William D., Koh Jeong Hwan, Gagné Michel R.: Platinum(II)-Catalyzed 1,6-Diene Cycloisomerizations:  Turnover in the Absence of β-Hydride Elimination. Org Lett 2004, 6, 3013. <http://dx.doi.org/10.1021/ol048780u>
  • Dimitrov Vladimir, Hopp Rentsch Gudrun, Linden Anthony, Hesse Manfred: The Ozonolysis of Longifolene: A Tool for the Preparation of Useful Chiral Compounds. Configuration Determination of New Stereogenic Centers by NMR Spectroscopy and X-Ray Crystallography. HCA 2003, 86, 106. <http://dx.doi.org/10.1002/hlca.200390000>
  • Bülow Nils, König Wilfried A: The role of germacrene D as a precursor in sesquiterpene biosynthesis: investigations of acid catalyzed, photochemically and thermally induced rearrangements. Phytochemisry 2000, 55, 141. <http://dx.doi.org/10.1016/S0031-9422(00)00266-1>
  • Paschall Chiana M., Hasserodt Jens, Jones Terri, Lerner Richard A., Janda Kim D., Christianson David W.: Konvergenz der Mechanismen eines katalytischen Antikörpers und einer Terpen-Cyclase: eine durch Carbokation-π-Elektronen-Wechselwirkung gesteuerte Polyencyclisierung. Angew Chem 1999, 111, 1859. <http://dx.doi.org/10.1002/(SICI)1521-3757(19990614)111:12<1859::AID-ANGE1859>3.0.CO;2-F>
  • Warmers Ute, Wihstutz Kolja, Bülow Nils, Fricke Christiane, König Wilfried A: Sesquiterpene constituents of the liverwort Calypogeia muelleriana. Phytochemisry 1998, 49, 1723. <http://dx.doi.org/10.1016/S0031-9422(98)00283-0>
  • Alchanati Iris, Patel Jo Ann Acreman, Liu Jinggao, Benedict Chauncey R., Stipanovic Robert D., Bell Alois A., Cui Yunxing, Magill Clint W.: The enzymatic cyclization of nerolidyl diphosphate by δ-cadinene synthase from cotton stele tissue infected with verticillium dahliae. Phytochemisry 1998, 47, 961. <http://dx.doi.org/10.1016/S0031-9422(98)80054-X>
  • Riehs G., Urban E.: EPC synthesis of (+)-heptelidic acid. Monatshefte für Chemie 1997, 128, 281. <http://dx.doi.org/10.1007/BF00807894>
  • Riehs Gerhard, Urban Ernst, Völlenkle Horst: A key step towards EPC synthesis of (+)-heptelidic acid. Tetrahedron 1996, 52, 8725. <http://dx.doi.org/10.1016/0040-4020(96)00428-0>
  • Davis Gordon D., Essenberg Margaret: (+)-δ-Cadinene is a product of sesquiterpene cyclase activity in cotton. Phytochemisry 1995, 39, 553. <http://dx.doi.org/10.1016/0031-9422(95)00067-H>
  • Rodriguez Juan B., Gros Eduardo G., Caram José A., Marschoff Carlos M.: Ritter reaction on terpenoids. IV. Remarkable tendency to produce 3-aza-bicyclo[3.3.1]non-2-ene systems from mono and sesquiterpenes. Tetrahetron Lett 1995, 36, 7825. <http://dx.doi.org/10.1016/0040-4039(95)01671-4>
  • Nabeta Kensuke, Mototani Yuki, Tazaki Hiroyuki, Okuyama Hiroshi: Biosynthesis of sesquiterpenes of cadinane type in cultured cells of Heteroscyphus planus. Phytochemisry 1994, 35, 915. <http://dx.doi.org/10.1016/S0031-9422(00)90638-1>
  • Breeden David C., Coates Robert M.: 7-Epizingiberene, A novel bisabolane sesquiterpene from wild tomato leaves. Tetrahedron 1994, 50, 11123. <http://dx.doi.org/10.1016/S0040-4020(01)89415-1>
  • Cane David E., Tandon Manish: Biosynthesis of (+)-epicubenol. Tetrahetron Lett 1994, 35, 5355. <http://dx.doi.org/10.1016/S0040-4039(00)73498-8>
  • Davis Gordon D., Eisenbraun E.J., Essenberg Margaret: Tritium transfer during biosynthesis of cadalene stress compounds in cotton. Phytochemisry 1991, 30, 197. <http://dx.doi.org/10.1016/0031-9422(91)84123-A>
  • Ghisalberti E.L., Sivasithamparam K.: Antifungal antibiotics produced by Trichoderma spp. Soil Biol Biochem 1991, 23, 1011. <http://dx.doi.org/10.1016/0038-0717(91)90036-J>
  • Sakai Kaoru, Hasumi Keiji, Endo Akira: Identification of koningic acid (heptelidic acid)-modified site in rabbit muscle glyceraldehyde-3-phosphate dehydrogenase. Biochimica et Biophysica Acta (BBA) - Protein Structure and Molecular Enzymology 1991, 1077, 192. <http://dx.doi.org/10.1016/0167-4838(91)90058-8>
  • Townsend Craig A, Basak Amit: Experiments and speculations on the role of oxidative cyclization chemistry in natural product biosynthesis. Tetrahedron 1991, 47, 2591. <http://dx.doi.org/10.1016/S0040-4020(01)81792-0>
  • Wagschal Kurt, Savage Thomas J., Croteau Rodney: Isotopically sensitive branching as a tool for evaluating multiple product formation by monoterpene cyclases. Tetrahedron 1991, 47, 5933. <http://dx.doi.org/10.1016/S0040-4020(01)86486-3>
  • Caccamese Salvatore, Amico Vincenzo, Neri Placido, Foti Mario: The structure of laurobtusol, a new rearranged sesquiterpenoid from the mediterranean red alga laurencia obtusa. Tetrahedron 1991, 47, 10101. <http://dx.doi.org/10.1016/S0040-4020(01)96059-4>
  • Akhila Anand, Rani Kumkum, Thakur Raghunath S.: Biosynthesis of artemisinic acid in Artemisia annua. Phytochemisry 1990, 29, 2129. <http://dx.doi.org/10.1016/0031-9422(90)83020-2>
  • Akgül Attila, Chialva Franco: Constituents of the essential oil ofEchinophora tenuifolia L. subsp.sibthorpiana (guss.) tutin from Turkey. Flavour Fragr J 1989, 4, 67. <http://dx.doi.org/10.1002/ffj.2730040206>
  • Maffei Massimo: A chemotype ofMentha longifolia (L.) hudson particularly rich in piperitenone oxide. Flavour Fragr J 1988, 3, 23. <http://dx.doi.org/10.1002/ffj.2730030105>
  • Dehal Shangara S., Croteau Rodney: Partial purification and characterization of two sesquiterpene cyclases from sage (Salvia officinalis) which catalyze the respective conversion of farnesyl pyrophosphate to humulene and caryophyllene. Archives of Biochemistry and Biophysics 1988, 261, 346. <http://dx.doi.org/10.1016/0003-9861(88)90350-5>
  • Akhila Anand, Sharma Pradeep K., Thakur Raghunath S.: Biosynthetic relationships of patchouli alcohol, seychellene and cycloseychellene in Pogostemon cablin. Phytochemisry 1988, 27, 2105. <http://dx.doi.org/10.1016/0031-9422(88)80105-5>
  • Sharma Pradeep K., Thakur Raghunath S., Akhila Anand: 1,2-Hydrogen shifts in the formation of the sesquithujane skeleton in ginger rhizomes. Phytochemisry 1988, 27, 3471. <http://dx.doi.org/10.1016/0031-9422(88)80750-7>
  • Croteau Rodney, Munck Sharon L., Akoh Casimir C., Fisk Henry J., Satterwhite D. Michael: Biosynthesis of the sesquiterpene patchoulol from farnesyl pyrophosphate in leaf extracts of Pogostemon cablin (patchouli): Mechanistic considerations. Archives of Biochemistry and Biophysics 1987, 256, 56. <http://dx.doi.org/10.1016/0003-9861(87)90425-5>
  • Akhila Anand, Sharma Pradeep K., Thakur Raghunath S.: 1,2-Hydrogen shifts during the biosynthesis of patchoulenes in Pogostemon cablin. Phytochemisry 1987, 26, 2705. <http://dx.doi.org/10.1016/S0031-9422(00)83576-1>
  • Lewis Norman G., Dubelsten Paul, Eberhardt Thomas L., Yamamoto Etsuo, Towers G.H.Neil: The E/Z isomerization step in the biosynthesis of Z-coniferyl alcohol in Fagus grandifolia. Phytochemisry 1987, 26, 2729. <http://dx.doi.org/10.1016/S0031-9422(00)83580-3>
  • Suga Takayuki, Hirata Toshifumi, Aoki Tadashi, Shishibori Tsuyoshi: Interconversion and cyclization of acyclic allylic pyrophosphates in the biosynthesis of cyclic monoterpenoids in higher plants. Phytochemisry 1986, 25, 2769. <http://dx.doi.org/10.1016/S0031-9422(00)83738-3>
  • Berry Katherine M., Perry Nigel B., Weavers Rex T.: Foliage sesquiterpenes of Dacrydium cupressinum: identification, variation and biosynthesis. Phytochemisry 1985, 24, 2893. <http://dx.doi.org/10.1016/0031-9422(85)80022-4>
  • Oppolzer Wolfgang, Godel Thierry: Syntheses of (±)- and Enantiomerically Pure (+)-Longifolene and of (±)- and Enantiomerically Pure (+)-Sativene by an Intramolecularde Mayo Reaction. HCA 1984, 67, 1154. <http://dx.doi.org/10.1002/hlca.19840670429>
  • Stipanovic Robert D., Howell Charles R.: The X-ray crystal structure determination, and biosynthetic studies of the antibiotic, heptelidic acid. Tetrahedron 1983, 39, 1103. <http://dx.doi.org/10.1016/S0040-4020(01)91872-1>
  • Ayer William A., Browne Lois M.: Terpenoid metabolites of mushrooms and related basidiomycetes. Tetrahedron 1981, 37, 2197. <http://dx.doi.org/10.1016/S0040-4020(01)97979-7>
  • Croteau Rodney, Felton Mark, Ronald Robert C.: Biosynthesis of monoterpenes: Preliminary characterization of l-endo-fenchol synthetase from fennel (Foeniculum vulgare) and evidence that no free intermediate is involved in the cyclization of geranyl pyrophosphate to the rearranged product. Archives of Biochemistry and Biophysics 1980, 200, 534. <http://dx.doi.org/10.1016/0003-9861(80)90385-9>
  • Cane David E.: The stereochemistry of allylic pyrophosphate metabolism. Tetrahedron 1980, 36, 1109. <http://dx.doi.org/10.1016/0040-4020(80)87011-6>
  • Corvers A., Scheers P.C.H., Castenmiller W.A.M., Buck H.M.: Model study for steroidal d/c ring closure in olefinic cyclization reactions; a mindo/3 study. Tetrahedron 1978, 34, 457. <http://dx.doi.org/10.1016/0040-4020(78)80034-9>
  • Anderson Niels H., Tseng Chia-Li W., Moore Ana, Ohta Yoshimoto: The structure of isobarbatene, the stable tricyclic end-point of the bazzanene-barbatene sesquiterpenes. Tetrahedron 1978, 34, 47. <http://dx.doi.org/10.1016/0040-4020(78)88034-X>
  • Banthorpe Derek V., Ekundayo Olusegun, Rowan Michael G.: Evidence for geraniol as an obligatory precursor of isothujone. Phytochemisry 1978, 17, 1111. <http://dx.doi.org/10.1016/S0031-9422(00)94299-7>
  • Banthorpe Derek V., Modawi Barakat M., Poots Ian, Rowan Michael G.: Redox interconversions of geraniol and nerol in higher plants. Phytochemisry 1978, 17, 1115. <http://dx.doi.org/10.1016/S0031-9422(00)94300-0>
  • Itoh Akira, Nozaki Hitosi, Yamamoto Hisashi: Studies on the mechanism of sesquiterpene biosynthesis humulene-germacrene rearrangement. Tetrahetron Lett 1978, 19, 2903. <http://dx.doi.org/10.1016/S0040-4039(01)94894-4>
  • Herz Werner: Biogenetic Aspects of Sesquiterpene Lactone Chemistry. Isr. J. Chem. 1977, 16, 32. <http://dx.doi.org/10.1002/ijch.197700010>
  • Andersen Neils H., Bissonette P., Liu C.-B., Shunk Belinda, Ohta Yoshimoto, Tseng Chia-Li W., Moore Ana, Huneck S.: Sesquiterpenes of nine european liverworts from the genera, Anastrepta, bazzania, jungermannia, lepidozia and Scapania. Phytochemisry 1977, 16, 1731. <http://dx.doi.org/10.1016/0031-9422(71)85081-1>
  • MACKIE Hugh, OVERTON Karl H.: Hydrolysis and Isomerization of trans,trans-Farnesyl Diphosphate by Andrographis Tissue-Culture Enzymes. Eur J Biochem 1977, 77, 101. <http://dx.doi.org/10.1111/j.1432-1033.1977.tb11646.x>