메뉴 건너뛰기




Volumn 21, Issue 11, 2014, Pages 1452-1456

Conversion of substrate analogs suggests a michael cyclization in iridoid biosynthesis

Author keywords

[No Author keywords available]

Indexed keywords

IRIDOID; IRIDOID SYNTHASE; SYNTHETASE; UNCLASSIFIED DRUG; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; TERPENE; TRANSFERASE;

EID: 84911903392     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2014.09.010     Document Type: Article
Times cited : (32)

References (29)
  • 1
    • 77955429038 scopus 로고    scopus 로고
    • Highly conserved progesterone 5 β-reductase genes (P5 β R) from 5 β-cardenolide-free and 5 β-cardenolide-producing angiosperms
    • P. Bauer, J. Munkert, M. Brydziun, E. Burda, F. Müller-Uri, H. Gröger, Y.A. Muller, and W. Kreis Highly conserved progesterone 5 β-reductase genes (P5 β R) from 5 β-cardenolide-free and 5 β-cardenolide-producing angiosperms Phytochemistry 71 2010 1495 1505
    • (2010) Phytochemistry , vol.71 , pp. 1495-1505
    • Bauer, P.1    Munkert, J.2    Brydziun, M.3    Burda, E.4    Müller-Uri, F.5    Gröger, H.6    Muller, Y.A.7    Kreis, W.8
  • 3
    • 79953251042 scopus 로고    scopus 로고
    • The family of terpene synthases in plants: A mid-size family of genes for specialized metabolism that is highly diversified throughout the kingdom
    • F. Chen, D. Tholl, J. Bohlmann, and E. Pichersky The family of terpene synthases in plants: a mid-size family of genes for specialized metabolism that is highly diversified throughout the kingdom Plant J. 66 2011 212 229
    • (2011) Plant J. , vol.66 , pp. 212-229
    • Chen, F.1    Tholl, D.2    Bohlmann, J.3    Pichersky, E.4
  • 5
    • 70350731753 scopus 로고    scopus 로고
    • Monoterpene and sesquiterpene synthases and the origin of terpene skeletal diversity in plants
    • J. Degenhardt, T.G. Köllner, and J. Gershenzon Monoterpene and sesquiterpene synthases and the origin of terpene skeletal diversity in plants Phytochemistry 70 2009 1621 1637
    • (2009) Phytochemistry , vol.70 , pp. 1621-1637
    • Degenhardt, J.1    Köllner, T.G.2    Gershenzon, J.3
  • 6
    • 77956441090 scopus 로고    scopus 로고
    • Aphid pheromones
    • L. Gerald, Academic Press San Diego
    • S.Y. Dewhirst, J.A. Pickett, and J. Hardie Aphid pheromones L. Gerald, Vitamins and Hormones Volume 83 2010 Academic Press San Diego 551 574
    • (2010) Vitamins and Hormones , vol.83 VOLUME , pp. 551-574
    • Dewhirst, S.Y.1    Pickett, J.A.2    Hardie, J.3
  • 7
    • 79959791464 scopus 로고    scopus 로고
    • Naturally occurring iridoids and secoiridoids. An updated review, part 4
    • B. Dinda, S. Debnath, and R. Banik Naturally occurring iridoids and secoiridoids. An updated review, part 4 Chem. Pharm. Bull. (Tokyo) 59 2011 803 833
    • (2011) Chem. Pharm. Bull. (Tokyo) , vol.59 , pp. 803-833
    • Dinda, B.1    Debnath, S.2    Banik, R.3
  • 9
    • 77957276543 scopus 로고    scopus 로고
    • Reconstitution of a fungal meroterpenoid biosynthesis reveals the involvement of a novel family of terpene cyclases
    • T. Itoh, K. Tokunaga, Y. Matsuda, I. Fujii, I. Abe, Y. Ebizuka, and T. Kushiro Reconstitution of a fungal meroterpenoid biosynthesis reveals the involvement of a novel family of terpene cyclases Nat. Chem. 2 2010 858 864
    • (2010) Nat. Chem. , vol.2 , pp. 858-864
    • Itoh, T.1    Tokunaga, K.2    Matsuda, Y.3    Fujii, I.4    Abe, I.5    Ebizuka, Y.6    Kushiro, T.7
  • 11
    • 84862786646 scopus 로고    scopus 로고
    • Current developments and challenges in the search for a naturally selected Diels-Alderase
    • H.J. Kim, M.W. Ruszczycky, and H.-W. Liu Current developments and challenges in the search for a naturally selected Diels-Alderase Curr. Opin. Chem. Biol. 16 2012 124 131
    • (2012) Curr. Opin. Chem. Biol. , vol.16 , pp. 124-131
    • Kim, H.J.1    Ruszczycky, M.W.2    Liu, H.-W.3
  • 14
    • 0037087588 scopus 로고    scopus 로고
    • The hetero-Diels-Alder addition of sulfur dioxide to 1-fluorobuta-1,3-dienes: The sofa conformations preferred by 6-fluorosultines (6-fluoro-3,6-dihydro-1,2-oxathiin-2-oxides) enjoy enthalpic and conformational Anomeric effects
    • E. Roversi, R. Scopelliti, E. Solari, R. Estoppey, P. Vogel, P. Braña, B. Menéndez, and J.A. Sordo The hetero-Diels-Alder addition of sulfur dioxide to 1-fluorobuta-1,3-dienes: the sofa conformations preferred by 6-fluorosultines (6-fluoro-3,6-dihydro-1,2-oxathiin-2-oxides) enjoy enthalpic and conformational Anomeric effects Chemistry 8 2002 1336 1355
    • (2002) Chemistry , vol.8 , pp. 1336-1355
    • Roversi, E.1    Scopelliti, R.2    Solari, E.3    Estoppey, R.4    Vogel, P.5    Braña, P.6    Menéndez, B.7    Sordo, J.A.8
  • 15
    • 84899427362 scopus 로고    scopus 로고
    • Truncation of N-terminal regions of Digitalis lanata progesterone 5β-reductase alters catalytic efficiency and substrate preference
    • K. Rudolph, P. Bauer, B. Schmid, F. Mueller-Uri, and W. Kreis Truncation of N-terminal regions of Digitalis lanata progesterone 5β-reductase alters catalytic efficiency and substrate preference Biochimie 101 2014 31 38
    • (2014) Biochimie , vol.101 , pp. 31-38
    • Rudolph, K.1    Bauer, P.2    Schmid, B.3    Mueller-Uri, F.4    Kreis, W.5
  • 16
  • 17
    • 47749101233 scopus 로고    scopus 로고
    • The crystal structure of progesterone 5β-reductase from Digitalis lanata defines a novel class of short chain dehydrogenases/reductases
    • A. Thorn, C. Egerer-Sieber, C.M. Jäger, V. Herl, F. Müller-Uri, W. Kreis, and Y.A. Muller The crystal structure of progesterone 5β-reductase from Digitalis lanata defines a novel class of short chain dehydrogenases/reductases J. Biol. Chem. 283 2008 17260 17269
    • (2008) J. Biol. Chem. , vol.283 , pp. 17260-17269
    • Thorn, A.1    Egerer-Sieber, C.2    Jäger, C.M.3    Herl, V.4    Müller-Uri, F.5    Kreis, W.6    Muller, Y.A.7
  • 18
    • 0343073844 scopus 로고
    • Iridoids. Part 19. Stereoselective synthesis of iridoid glycosides
    • L.-F. Tietze Iridoids. Part 19. Stereoselective synthesis of iridoid glycosides Angew. Chem. Int. Ed. Engl. 22 1983 828 841
    • (1983) Angew. Chem. Int. Ed. Engl. , vol.22 , pp. 828-841
    • Tietze, L.-F.1
  • 19
    • 84986671032 scopus 로고
    • Inter- and intramolecular hetero Diels-Alder reactions. 32. Iridoids. 26. Synthesis of bridged homoiridoids from secologanin by tandem Knoevenagel-hetero-Diels-Alder reactions
    • L.-F. Tietze, and C. Bartels Inter- and intramolecular hetero Diels-Alder reactions. 32. Iridoids. 26. Synthesis of bridged homoiridoids from secologanin by tandem Knoevenagel-hetero-Diels-Alder reactions Liebigs Ann. Chem. 2 1991 155 160
    • (1991) Liebigs Ann. Chem. , vol.2 , pp. 155-160
    • Tietze, L.-F.1    Bartels, C.2
  • 20
    • 0018849567 scopus 로고
    • Stereocontrolled intramolecular Diels-Alder reaction of heterodienes; Studies on the synthesis of cannabinoids
    • L.-F. Tietze, G. von Kiedrowski, K. Harms, W. Clegg, and G. Sheldrick Stereocontrolled intramolecular Diels-Alder reaction of heterodienes; studies on the synthesis of cannabinoids Angew. Chem. 19 1980 130 131
    • (1980) Angew. Chem. , vol.19 , pp. 130-131
    • Tietze, L.-F.1    Von Kiedrowski, G.2    Harms, K.3    Clegg, W.4    Sheldrick, G.5
  • 21
    • 0043137462 scopus 로고
    • Intramolecular cycloadditions. Part 4. Stereo- and regioselective syntheses of enantiomerically pure (+)- and (-)-hexahydrocannabinol by intramolecular cycloaddition
    • L.-F. Tietze, G. von Kiedrowski, and B. Berger Intramolecular cycloadditions. Part 4. Stereo- and regioselective syntheses of enantiomerically pure (+)- and (-)-hexahydrocannabinol by intramolecular cycloaddition Angew. Chem. 21 1982 222 223
    • (1982) Angew. Chem. , vol.21 , pp. 222-223
    • Tietze, L.-F.1    Von Kiedrowski, G.2    Berger, B.3
  • 23
    • 85008530425 scopus 로고
    • Mechanism of iridane skeleton formation in the biosynthesis of iridoid glucosides in Gardenia jasminoides cell cultures
    • S. Uesato, S. Ueda, K. Kobayashi, and H. Inouye Mechanism of iridane skeleton formation in the biosynthesis of iridoid glucosides in Gardenia jasminoides cell cultures Chem. Pharm. Bull. (Tokyo) 31 1983 4185 4188
    • (1983) Chem. Pharm. Bull. (Tokyo) , vol.31 , pp. 4185-4188
    • Uesato, S.1    Ueda, S.2    Kobayashi, K.3    Inouye, H.4
  • 24
    • 85011164135 scopus 로고
    • Mechanism for iridane skeleton formation from acyclic monoterpenes in the biosynthesis of secologanin and vindoline in Catharanthus roseus and Lonicera morrowii
    • S. Uesato, S. Matsuda, and H. Inouye Mechanism for iridane skeleton formation from acyclic monoterpenes in the biosynthesis of secologanin and vindoline in Catharanthus roseus and Lonicera morrowii Chem. Pharm. Bull. (Tokyo) 32 1984 1671 1674
    • (1984) Chem. Pharm. Bull. (Tokyo) , vol.32 , pp. 1671-1674
    • Uesato, S.1    Matsuda, S.2    Inouye, H.3
  • 25
    • 0023219327 scopus 로고
    • Elucidation of iridodial formation mechanism. Partial purification and characterization of the novel monoterpene cyclase from Rauwolfia serpentina cell suspension cultures
    • S. Uesato, H. Ikeda, T. Fujita, H. Inouye, and M.H. Zenk Elucidation of iridodial formation mechanism. Partial purification and characterization of the novel monoterpene cyclase from Rauwolfia serpentina cell suspension cultures Tetrahedron Lett. 28 1987 4431 4434
    • (1987) Tetrahedron Lett. , vol.28 , pp. 4431-4434
    • Uesato, S.1    Ikeda, H.2    Fujita, T.3    Inouye, H.4    Zenk, M.H.5
  • 27
    • 84867063817 scopus 로고    scopus 로고
    • Bacterial synthesis of diverse indole terpene alkaloids by an unparalleled cyclization sequence
    • Z. Xu, M. Baunach, L. Ding, and C. Hertweck Bacterial synthesis of diverse indole terpene alkaloids by an unparalleled cyclization sequence Angew. Chem. Int. Ed. Engl. 51 2012 10293 10297
    • (2012) Angew. Chem. Int. Ed. Engl. , vol.51 , pp. 10293-10297
    • Xu, Z.1    Baunach, M.2    Ding, L.3    Hertweck, C.4
  • 29
    • 81855166715 scopus 로고    scopus 로고
    • Selective fluoroalkylation of organic compounds by tackling the "negative fluorine effect"
    • W. Zhang, C. Ni, and J. Hu Selective fluoroalkylation of organic compounds by tackling the "negative fluorine effect" Top. Curr. Chem. 308 2012 25 44
    • (2012) Top. Curr. Chem. , vol.308 , pp. 25-44
    • Zhang, W.1    Ni, C.2    Hu, J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.