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Volumn 8, Issue 15, 2007, Pages 1826-1833

Interception of the enzymatic conversion of farnesyl diphosphate to 5-epi-aristolochene by using a fluoro substrate analogue: 1-Fluorogermacrene A from (2E,6Z)-6-fluorofarnesyl diphosphate

Author keywords

Biosynthesis; Carbocations; Enzyme catalysis; Farnesyl diphosphate; Fluorine; Terpenoids

Indexed keywords

1 FLUOROGERMACRENE A; 5 EPI ARISTOLOCHENE; 6 FLUOROFARNESYL DIOPHOSPHATE; ALKADIENE; ARISTOLOCHENE; FARNESYL DIPHOSPHATE; FLUOROCYCLODECADIENE; PYROPHOSPHATE; TERPENOID; UNCLASSIFIED DRUG;

EID: 35348952662     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200700398     Document Type: Article
Times cited : (40)

References (62)
  • 1
    • 35348998964 scopus 로고    scopus 로고
    • E. M. Davis, R. Croteau in Topics in Current Chemistry, 209: Biosynthesis: Aromatic Polyketides, lsoprenoids, Alkaloids (Eds.: F. Leeper, J. C. Vederas), Springer, Heidelberg, 2000, pp. 53-95;
    • a) E. M. Davis, R. Croteau in Topics in Current Chemistry, Vol. 209: Biosynthesis: Aromatic Polyketides, lsoprenoids, Alkaloids (Eds.: F. Leeper, J. C. Vederas), Springer, Heidelberg, 2000, pp. 53-95;
  • 3
    • 35349028319 scopus 로고    scopus 로고
    • Isoprenoids Including Carotenoids and Steroids D. E. Cane in Comprehensive Natural Products Chemistry, 2 (Eds.: D. Barton, K. Nakanishi, O. Meth-Cohn), Elsevier, Amsterdam, 1999.
    • c) "Isoprenoids Including Carotenoids and Steroids" D. E. Cane in Comprehensive Natural Products Chemistry, Vol. 2 (Eds.: D. Barton, K. Nakanishi, O. Meth-Cohn), Elsevier, Amsterdam, 1999.
  • 4
    • 0002510225 scopus 로고    scopus 로고
    • Eds, D. Barton, K. Nakanishi, O. Meth-Cohn, Elsevier, Amsterdam
    • a) M. L. Wise, R. Croteau in Comprehensive Natural Products Chemistry, Vol. 2. (Eds.: D. Barton, K. Nakanishi, O. Meth-Cohn), Elsevier, Amsterdam, 1999, pp. 97-153;
    • (1999) Comprehensive Natural Products Chemistry , vol.2 , pp. 97-153
    • Wise, M.L.1    Croteau, R.2
  • 5
    • 0001182551 scopus 로고    scopus 로고
    • Eds, D. Barton, K. Nakanishi, O. Meth-Cohn, Elsevier, Amsterdam
    • b) D. E. Cane in Comprehensive Natural Products Chemistry, Vol. 2. (Eds.: D. Barton, K. Nakanishi, O. Meth-Cohn), Elsevier, Amsterdam, 1999, pp. 155-200.
    • (1999) Comprehensive Natural Products Chemistry , vol.2 , pp. 155-200
    • Cane, D.E.1
  • 11
    • 4644328108 scopus 로고    scopus 로고
    • For reviews see: a
    • For reviews see: a) R. Pongdee, H.-w. Liu, Bioorg. Chem. 2004, 32, 393-437;
    • (2004) Bioorg. Chem , vol.32 , pp. 393-437
    • Pongdee, R.1    Liu, H.-W.2
  • 22
    • 0000558630 scopus 로고
    • b) D. E. Cane, Chem. Rev. 1990, 90, 1089-1103.
    • (1990) Chem. Rev , vol.90 , pp. 1089-1103
    • Cane, D.E.1
  • 25
    • 35349007961 scopus 로고    scopus 로고
    • The preceding article by Miller, Yu, and Allemann reports the enzymatic cydization of 2-fluorofarnesyl PP to 5-fluorogermacrene A with recombinant aristolochene synthase from Penicillium roqueforti.
    • The preceding article by Miller, Yu, and Allemann reports the enzymatic cydization of 2-fluorofarnesyl PP to 5-fluorogermacrene A with recombinant aristolochene synthase from Penicillium roqueforti.
  • 36
  • 40
    • 35349016830 scopus 로고    scopus 로고
    • 1H NMR signals.
    • 1H NMR signals.
  • 41
    • 0000028063 scopus 로고    scopus 로고
    • The conformations of flexible germacrenes are denoted as UU, DD, UD and DU. U (up) and D (down) refer to the orientations of C14 and C15 methyl groups; a) J. K. Sutherland, Tetrahedron 1974, 30, 1651-1660;
    • The conformations of flexible germacrenes are denoted as UU, DD, UD and DU. U (up) and D (down) refer to the orientations of C14 and C15 methyl groups; a) J. K. Sutherland, Tetrahedron 1974, 30, 1651-1660;
  • 43
    • 35348997398 scopus 로고    scopus 로고
    • (+)-Germacrene A behaves in solution (25°C) as a 5:3:2 mixture of UU, UD, and DU conformers, respectively. See ref. [24].
    • (+)-Germacrene A behaves in solution (25°C) as a 5:3:2 mixture of UU, UD, and DU conformers, respectively. See ref. [24].
  • 44
    • 3042988525 scopus 로고
    • -1) of the four possible conformers of 1-fluorogermacrene A calculated by the Allinger MM2 force-field method were as follows: UU (0.00, UD (0.55, DD (1.85, and DU 1.96
    • -1) of the four possible conformers of 1-fluorogermacrene A calculated by the Allinger MM2 force-field method were as follows: UU (0.00), UD (0.55), DD (1.85), and DU (1.96).
    • (1977) J. Am. Chem. Soc , vol.99 , pp. 8127-8134
    • Allinger, N.L.1
  • 49
    • 35348930471 scopus 로고    scopus 로고
    • In the absence of any independent evidence concerning the enantiomeric purity and absolute configuration of the, )-1-fluorogermacrene A product, we assume that the fluoro analogue has the same 7R stereochemistry of the isopropenyl group as 5-epi-aristolochene 4, since both are produced by TEAS with comparable catalytic efficiencies
    • In the absence of any independent evidence concerning the enantiomeric purity and absolute configuration of the (-)-1-fluorogermacrene A product, we assume that the fluoro analogue has the same 7R stereochemistry of the isopropenyl group as 5-epi-aristolochene (4), since both are produced by TEAS with comparable catalytic efficiencies.
  • 50
    • 0030796451 scopus 로고    scopus 로고
    • X-ray analysis of the structure of TEAS in combination with studies regarding the catalytic properties of a TEAS mutant suggests that Tyr520 participates as an active-site acid that protonates, -germacrene A. See C. M. Starks, K. Back, J. Chappell, J. P. Noel, Science 1997, 277, 1815-1820 and ref, 3
    • X-ray analysis of the structure of TEAS in combination with studies regarding the catalytic properties of a TEAS mutant suggests that Tyr520 participates as an active-site acid that protonates (+)-germacrene A. See C. M. Starks, K. Back, J. Chappell, J. P. Noel, Science 1997, 277, 1815-1820 and ref. [3].
  • 60
    • 35348995432 scopus 로고    scopus 로고
    • Evidence supporting germacrene A as a neutral intermediate in TEAS and aristolochene synthase catalysis has been provided by Chappell,[3] Allemann,[4a] and Cane[4b] through site-directed mutagenesis
    • [4b] through site-directed mutagenesis.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.