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ChemBioChem
Volumn 10, Issue 10, 2009, Pages 1697-1704
Epoxide-hydrolase-initiated hydrolysis/rearrangement cascade of a methylene-interrupted bis-epoxide yields chiral THF moieties without involvement of a "Cyclase"
Author keywords

Bis epoxides; Cascade reactions; Enzyme models; Epoxide hydrolases; Hydrolases
Indexed keywords

ACETOGENIN; CARBENE; EPOXIDE HYDROLASE; NATURAL PRODUCT; TETRAHYDROFURAN;
EID: 70349558158     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200900176     Document Type: Article
Times cited : (18)
References (56)
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    • The antileukemic agent uvaricin was discovered as the first representative in 1982; see M. S. Tempesta, G. R. Kriek, R. B. Bates, J. Org. Chem. 1982, 47, 3151-3153.
    • The antileukemic agent uvaricin was discovered as the first representative in 1982; see M. S. Tempesta, G. R. Kriek, R. B. Bates, J. Org. Chem. 1982, 47, 3151-3153.
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    • II, Type I cyclases) activation of an allylic diphosphate precursor or the Brønsted-acid-mediated (Asp, I cyclases) electrophilic activation of an olefin or an epoxide. The initiation step creates a carbenium ion, which is immediately trapped by an adjacent alkene, and generates the next carbenium ion, and so forth. Finally, this electrophilic cascade is terminated either by deprotonation (or by hydration) of the last carbenium ion to furnish an alkene (or an alcohol) as the final product of the cyclisation cascade. For reviews see: D. W. Christianson, Chem. Rev. 2006, 106, 3412-3442;
    • II, Type I cyclases) activation of an allylic diphosphate precursor or the Brønsted-acid-mediated (Asp, I cyclases) electrophilic activation of an olefin or an epoxide. The initiation step creates a carbenium ion, which is immediately trapped by an adjacent alkene, and generates the next carbenium ion, and so forth. Finally, this electrophilic cascade is terminated either by deprotonation (or by hydration) of the last carbenium ion to furnish an alkene (or an alcohol) as the final product of the cyclisation cascade. For reviews see: D. W. Christianson, Chem. Rev. 2006, 106, 3412-3442;
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    • Although enzymes obey the Baldwin rules in general, exceptional anti-Baldwinor anti-Markovnikov cyclisations are known; cf
    • J. E. Baldwin, J. Chem. Soc. Chem. Commun. 1976, 734-738. Although enzymes obey the Baldwin rules in general, exceptional anti-Baldwinor anti-Markovnikov cyclisations are known; cf. ref. 15
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    • Recently, the first enzymes that disobey Baldwin's rules were found in the biosynthesis of the polyether antibiotic lasalocid. LasB/Lsd19 epoxide hydrolases catalyse the ring-closure of a bis-epoxy-alcohol precursor through a disfavoured 6-endo-tet cyclisation, instead of the favoured 5-exo-tet cyclisation, see: Y. Shichijo, A. Migita, H. Oguri, M. Watanabe, T. Tokiwano, K. Watanabe, H. Oikawa, J. Am. Chem. Soc. 2008, 130, 12230-12231;
    • Recently, the first enzymes that disobey Baldwin's rules were found in the biosynthesis of the polyether antibiotic lasalocid. LasB/Lsd19 epoxide hydrolases catalyse the ring-closure of a bis-epoxy-alcohol precursor through a disfavoured 6-endo-tet cyclisation, instead of the favoured 5-exo-tet cyclisation, see: Y. Shichijo, A. Migita, H. Oguri, M. Watanabe, T. Tokiwano, K. Watanabe, H. Oikawa, J. Am. Chem. Soc. 2008, 130, 12230-12231;
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    • for a review on enzyme-initiated cascade-reactions see
    • for a review on enzyme-initiated cascade-reactions see: S. F. Mayer, W. Kroutil, K. Faber, Chem. Soc. Rev. 2001, 30, 332-339.
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    • For the epoxide hydrolase from Agrobacterium radiobacter see: M. Nardini, R. Rink, D. B. Janssen, B. W. Dijkstra, J. Mol. Catal. B 2001, 11, 1035-1042;
    • For the epoxide hydrolase from Agrobacterium radiobacter see: M. Nardini, R. Rink, D. B. Janssen, B. W. Dijkstra, J. Mol. Catal. B 2001, 11, 1035-1042;
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    • for the epoxide hydrolase from A. niger see: J. Zou, B. M. Hallberg, T. Bergfors, F. Oesch, M. Arand, S. L. Mowbray, T. A. Jones, Structure 2000, 8, 111-122.
    • for the epoxide hydrolase from A. niger see: J. Zou, B. M. Hallberg, T. Bergfors, F. Oesch, M. Arand, S. L. Mowbray, T. A. Jones, Structure 2000, 8, 111-122.
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    • For limonene 1,2-epoxide hydrolase from Rhododoccus erythropolis see: M. Arand, B. M. Hallberg, J. Zou, T. Bergfors, F. Oesch, M. J. van der Werf, J. A. M. de Bont, T. A. Jones, S. L. Mowbray, EMBO J. 2003, 22, 2583-2592.
    • For limonene 1,2-epoxide hydrolase from Rhododoccus erythropolis see: M. Arand, B. M. Hallberg, J. Zou, T. Bergfors, F. Oesch, M. J. van der Werf, J. A. M. de Bont, T. A. Jones, S. L. Mowbray, EMBO J. 2003, 22, 2583-2592.
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    • Although the Gibbs free energies (ΔGreact) for both cyclisation pathways were ∼17 kcalmol-1, a significant energetic discrimination of ∼3 kcalmol-1 was found between deprotonation energies of alcohol groups of epoxy-diol intermediates, thereby favouring pathway F over E, which (translated into kinetic terms) is >99, see ref, 18
    • -1 was found between deprotonation energies of alcohol groups of epoxy-diol intermediates, thereby favouring pathway F over E, which (translated into kinetic terms) is >99%; see ref. [18].
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    • Likewise, LEH was shown to hydrolyse both enantiomers of its natural substrate (limonene-1,2-epoxide) in an enantioconvergent fashion through opposite regioselective nucleophilic attack; see ref. [24].
    • Likewise, LEH was shown to hydrolyse both enantiomers of its natural substrate (limonene-1,2-epoxide) in an enantioconvergent fashion through opposite regioselective nucleophilic attack; see ref. [24].
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.