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Volumn 87, Issue 12, 2012, Pages 1709-1714

Promiscuous enzyme-catalyzed Michael addition: Synthesis of warfarin and derivatives

Author keywords

Biocatalysis; Lipase from porcine pancreas; Michael addition; Warfarin

Indexed keywords

ADDITION REACTIONS; CATALYSIS; ENANTIOSELECTIVITY;

EID: 84869156712     PISSN: 02682575     EISSN: 10974660     Source Type: Journal    
DOI: 10.1002/jctb.3830     Document Type: Article
Times cited : (42)

References (46)
  • 1
    • 0033117461 scopus 로고    scopus 로고
    • Catalytic promiscuity and the evolution of new enzymatic activities
    • O'Brien PJ and Herschlag D, Catalytic promiscuity and the evolution of new enzymatic activities. Chem Biol 6: 91-105 (1999).
    • (1999) Chem Biol , vol.6 , pp. 91-105
    • O'Brien, P.J.1    Herschlag, D.2
  • 2
    • 0037396292 scopus 로고    scopus 로고
    • Enzymes with extra talents: moonlighting functions and catalytic promiscuity
    • Copley SD, Enzymes with extra talents: moonlighting functions and catalytic promiscuity. Curr Opin Chem Biol 7: 265-272 (2003).
    • (2003) Curr Opin Chem Biol , vol.7 , pp. 265-272
    • Copley, S.D.1
  • 3
    • 33748525883 scopus 로고    scopus 로고
    • Enzyme promiscuity: evolutionary and mechanistic aspects
    • Khersonsky O, Roodveldt C and Tawfik DS, Enzyme promiscuity: evolutionary and mechanistic aspects. Curr Opin Chem Biol 10: 498-508 (2006).
    • (2006) Curr Opin Chem Biol , vol.10 , pp. 498-508
    • Khersonsky, O.1    Roodveldt, C.2    Tawfik, D.S.3
  • 5
    • 67650603638 scopus 로고    scopus 로고
    • Design of α-Transglucosidases of controlled specificity for programmed chemoenzymatic synthesis of antigenic oligosaccharides
    • Champion E, André I, Moulis C, Boutet J, Descroix K, Morel S, et al, Design of α-Transglucosidases of controlled specificity for programmed chemoenzymatic synthesis of antigenic oligosaccharides. J Am Chem Soc 131: 7379-7389 (2009).
    • (2009) J Am Chem Soc , vol.131 , pp. 7379-7389
    • Champion, E.1    André, I.2    Moulis, C.3    Boutet, J.4    Descroix, K.5    Morel, S.6
  • 6
    • 77958046500 scopus 로고    scopus 로고
    • Hydrolases: catalytically promiscuous enzymes for non-conventional reactions in organic synthesis
    • Busto E, Gotor-Fernández V and Gotor V, Hydrolases: catalytically promiscuous enzymes for non-conventional reactions in organic synthesis. Chem Soc Rev 39: 4504-4523 (2010).
    • (2010) Chem Soc Rev , vol.39 , pp. 4504-4523
    • Busto, E.1    Gotor-Fernández, V.2    Gotor, V.3
  • 7
    • 10044248344 scopus 로고    scopus 로고
    • Catalytic promiscuity in biocatalysis: using old enzymes to form new bonds and follow new pathways
    • Bornscheuer UT and Kazlauskas RJ, Catalytic promiscuity in biocatalysis: using old enzymes to form new bonds and follow new pathways. Angew Chem Int Ed 43: 6032-6040 (2004).
    • (2004) Angew Chem Int Ed , vol.43 , pp. 6032-6040
    • Bornscheuer, U.T.1    Kazlauskas, R.J.2
  • 8
    • 77958009739 scopus 로고    scopus 로고
    • Enzymatic promiscuity for organic synthesis and cascade process
    • Wu Q, Liu BK and Lin XF, Enzymatic promiscuity for organic synthesis and cascade process. Curr Org Chem 14: 1966-1988 (2010).
    • (2010) Curr Org Chem , vol.14 , pp. 1966-1988
    • Wu, Q.1    Liu, B.K.2    Lin, X.F.3
  • 9
    • 79959757238 scopus 로고    scopus 로고
    • Biocatalytic promiscuity
    • Humble MS and Berglund P, Biocatalytic promiscuity. Eur J Org Chem 2011: 3391-3401 (2011).
    • (2011) Eur J Org Chem , vol.2011 , pp. 3391-3401
    • Humble, M.S.1    Berglund, P.2
  • 10
    • 0033635683 scopus 로고    scopus 로고
    • Enzymatic asymmetric synthesis by decarboxylases
    • Ward OP and Singh A, Enzymatic asymmetric synthesis by decarboxylases. Curr Opin Biotechnol 11: 520-526 (2000).
    • (2000) Curr Opin Biotechnol , vol.11 , pp. 520-526
    • Ward, O.P.1    Singh, A.2
  • 11
    • 59849106371 scopus 로고    scopus 로고
    • Protein promiscuity and its implications for biotechnology
    • Nobeli I, Favia AD and Thornton JM, Protein promiscuity and its implications for biotechnology. Nat Biotechnol 27: 157-167 (2009).
    • (2009) Nat Biotechnol , vol.27 , pp. 157-167
    • Nobeli, I.1    Favia, A.D.2    Thornton, J.M.3
  • 12
    • 34247131307 scopus 로고    scopus 로고
    • Enzyme promiscuity: mechanism and applications
    • Hult K and Berglund P, Enzyme promiscuity: mechanism and applications. Trends Biotechnol 25: 231-238 (2007).
    • (2007) Trends Biotechnol , vol.25 , pp. 231-238
    • Hult, K.1    Berglund, P.2
  • 14
    • 44649139781 scopus 로고    scopus 로고
    • Biocatalytic promiscuity: the first lipase-catalysed asymmetric aldol reaction
    • Li C, Feng XW, Wang N, Zhou YJ and Yu XQ, Biocatalytic promiscuity: the first lipase-catalysed asymmetric aldol reaction. Green Chem 10: 616-618 (2008).
    • (2008) Green Chem , vol.10 , pp. 616-618
    • Li, C.1    Feng, X.W.2    Wang, N.3    Zhou, Y.J.4    Yu, X.Q.5
  • 15
    • 78650927264 scopus 로고    scopus 로고
    • Protease-catalyzed direct aldol reaction
    • Li HH, He YH and Guan Z, Protease-catalyzed direct aldol reaction. Catal Commun 12: 580-582 (2011).
    • (2011) Catal Commun , vol.12 , pp. 580-582
    • Li, H.H.1    He, Y.H.2    Guan, Z.3
  • 16
    • 78651310908 scopus 로고    scopus 로고
    • Nuclease p1: a new biocatalyst for direct asymmetric aldol reaction under solvent-free conditions
    • Li HH, He YH, Yuan Y and Guan Z, Nuclease p1: a new biocatalyst for direct asymmetric aldol reaction under solvent-free conditions. Green Chem 13: 185-189 (2011).
    • (2011) Green Chem , vol.13 , pp. 185-189
    • Li, H.H.1    He, Y.H.2    Yuan, Y.3    Guan, Z.4
  • 17
    • 35448994419 scopus 로고    scopus 로고
    • Hydrolase-catalyzed Michael addition of 1,3-dicarbonyl compounds to α,β-unsaturated compounds in organic solvent
    • Xu JM, Zhang F, Wu Q, Zhang QY and Lin XF, Hydrolase-catalyzed Michael addition of 1, 3-dicarbonyl compounds to α, β-unsaturated compounds in organic solvent. J Mol Catal B: Enzym 49: 50-54 (2007).
    • (2007) J Mol Catal B: Enzym , vol.49 , pp. 50-54
    • Xu, J.M.1    Zhang, F.2    Wu, Q.3    Zhang, Q.Y.4    Lin, X.F.5
  • 18
    • 77958074145 scopus 로고    scopus 로고
    • Suppressed native hydrolytic activity of a lipase to reveal promiscuous Michael addition activity in water
    • Svedendahl M, Jovanović B, Fransson L and Berglund P, Suppressed native hydrolytic activity of a lipase to reveal promiscuous Michael addition activity in water. Chem Catal Chem 1: 252-258 (2009).
    • (2009) Chem Catal Chem , vol.1 , pp. 252-258
    • Svedendahl, M.1    Jovanović, B.2    Fransson, L.3    Berglund, P.4
  • 19
    • 4344647097 scopus 로고    scopus 로고
    • Lipase catalysed Michael addition of secondary amines to acrylonitrile
    • Torre O, Alfonso I and Gotor V, Lipase catalysed Michael addition of secondary amines to acrylonitrile. Chem Commun 15: 1724-1725 (2004).
    • (2004) Chem Commun , vol.15 , pp. 1724-1725
    • Torre, O.1    Alfonso, I.2    Gotor, V.3
  • 20
    • 34547398555 scopus 로고    scopus 로고
    • Promiscuous acylase-catalyzed aza-Michael additions of aromatic N-heterocycles in organic solvent
    • Qian C, Xu JM, Wu Q, Lv DS and Lin XF, Promiscuous acylase-catalyzed aza-Michael additions of aromatic N-heterocycles in organic solvent. Tetrahedron Lett 48: 6100-6104 (2007).
    • (2007) Tetrahedron Lett , vol.48 , pp. 6100-6104
    • Qian, C.1    Xu, J.M.2    Wu, Q.3    Lv, D.S.4    Lin, X.F.5
  • 21
    • 60149103177 scopus 로고    scopus 로고
    • Promiscuous enzyme-catalyzed regioselective Michael addition of purine derivatives to α,β-unsaturated carbonyl compounds in organic solvent
    • Wang JL, Xu JM, Wu Q, Lv DS and Lin XF, Promiscuous enzyme-catalyzed regioselective Michael addition of purine derivatives to α, β-unsaturated carbonyl compounds in organic solvent. Tetrahedron 65: 2531-2536 (2009).
    • (2009) Tetrahedron , vol.65 , pp. 2531-2536
    • Wang, J.L.1    Xu, J.M.2    Wu, Q.3    Lv, D.S.4    Lin, X.F.5
  • 22
    • 29844436474 scopus 로고    scopus 로고
    • Fast carbon-carbon bond formation by a promiscuous lipase
    • Svedendahl M, Hult K and Berglund P, Fast carbon-carbon bond formation by a promiscuous lipase. J Am Chem Soc 127: 17988-17989 (2005).
    • (2005) J Am Chem Soc , vol.127 , pp. 17988-17989
    • Svedendahl, M.1    Hult, K.2    Berglund, P.3
  • 23
    • 37049069286 scopus 로고
    • Synthesis of optically active trifluorinated compounds: asymmetric Michael addition with hydrolytic enzymes
    • Kitazume T, Ikeya T and Murata K, Synthesis of optically active trifluorinated compounds: asymmetric Michael addition with hydrolytic enzymes. J Chem Soc Chem Commun 1986: 1331-1333 (1986).
    • (1986) J Chem Soc Chem Commun , vol.1986 , pp. 1331-1333
    • Kitazume, T.1    Ikeya, T.2    Murata, K.3
  • 24
    • 67649114374 scopus 로고    scopus 로고
    • Lipase-catalysed direct Mannich reaction in water: utilization of biocatalytic promiscuity for C-C bond formation in a "one-pot" synthesis
    • Li K, He T, Li C, Feng XW, Wang N and Yu XQ, Lipase-catalysed direct Mannich reaction in water: utilization of biocatalytic promiscuity for C-C bond formation in a "one-pot" synthesis. Green Chem 6: 777-779 (2009).
    • (2009) Green Chem , vol.6 , pp. 777-779
    • Li, K.1    He, T.2    Li, C.3    Feng, X.W.4    Wang, N.5    Yu, X.Q.6
  • 25
    • 53849116830 scopus 로고    scopus 로고
    • Candida antarctica Lipase B (CAL-B)-catalyzed carbon-sulfur bond addition and controllable selectivity in organic media
    • Lou FW, Liu BK, Wu Q, Lv DS and Lin XF, Candida antarctica Lipase B (CAL-B)-catalyzed carbon-sulfur bond addition and controllable selectivity in organic media. Adv Synth Catal 350: 1959-1962 (2008).
    • (2008) Adv Synth Catal , vol.350 , pp. 1959-1962
    • Lou, F.W.1    Liu, B.K.2    Wu, Q.3    Lv, D.S.4    Lin, X.F.5
  • 26
    • 73749083243 scopus 로고    scopus 로고
    • Hydrolase-catalyzed fast Henry reaction of nitroalkanes and aldehydes in organic media
    • Wang JL, Li X, Xie HY, Liu BK and Lin XF, Hydrolase-catalyzed fast Henry reaction of nitroalkanes and aldehydes in organic media. J Biotechnol 145: 240-243 (2010).
    • (2010) J Biotechnol , vol.145 , pp. 240-243
    • Wang, J.L.1    Li, X.2    Xie, H.Y.3    Liu, B.K.4    Lin, X.F.5
  • 27
    • 0036525716 scopus 로고    scopus 로고
    • Lipases as practical biocatalysts
    • Reetz MT, Lipases as practical biocatalysts. Curr Opin Chem Biol 6: 145-150 (2002).
    • (2002) Curr Opin Chem Biol , vol.6 , pp. 145-150
    • Reetz, M.T.1
  • 28
    • 64549107504 scopus 로고    scopus 로고
    • Candida antarctica lipase B-catalyzed synthesis of acetamides using [BMIm(PF6)] as a reaction medium
    • Dhake KP, Qureshi ZS, Singhal RS and Bhanage BM, Candida antarctica lipase B-catalyzed synthesis of acetamides using [BMIm(PF6)] as a reaction medium. Tetrahedron Lett 50: 2811-2814 (2009).
    • (2009) Tetrahedron Lett , vol.50 , pp. 2811-2814
    • Dhake, K.P.1    Qureshi, Z.S.2    Singhal, R.S.3    Bhanage, B.M.4
  • 30
    • 4344647097 scopus 로고    scopus 로고
    • Lipase catalysed Michael addition of secondary amines to acrylonitrile
    • Torre O, Alfonso I and Gotor V, Lipase catalysed Michael addition of secondary amines to acrylonitrile. Chem Commun 2004: 1724-1725 (2004).
    • (2004) Chem Commun , vol.2004 , pp. 1724-1725
    • Torre, O.1    Alfonso, I.2    Gotor, V.3
  • 31
    • 77955422225 scopus 로고    scopus 로고
    • Promiscuous Candida antarctica lipase B-catalyzed synthesis of β-amino esters via aza-Michael addition of amines to acrylates
    • Dhake KP, Tambade PJ, Singhal RS and Bhanage BM, Promiscuous Candida antarctica lipase B-catalyzed synthesis of β-amino esters via aza-Michael addition of amines to acrylates. Tetrahedron Lett 51: 4455-4458 (2010).
    • (2010) Tetrahedron Lett , vol.51 , pp. 4455-4458
    • Dhake, K.P.1    Tambade, P.J.2    Singhal, R.S.3    Bhanage, B.M.4
  • 32
    • 0030580374 scopus 로고    scopus 로고
    • The first practical asymmetric synthesis of R and S-Warfarin
    • Robinson A, Li HY and Feaster J, The first practical asymmetric synthesis of R and S-Warfarin. Tetrahedron Lett 37: 8321-8324 (1996).
    • (1996) Tetrahedron Lett , vol.37 , pp. 8321-8324
    • Robinson, A.1    Li, H.Y.2    Feaster, J.3
  • 33
    • 0030515441 scopus 로고    scopus 로고
    • Enantioselective synthesis of 4-Hydroxy-3-(3-Oxo-1-Phenyl Butyl)-2H-1-Benzopyran-2-One (Warfarin)
    • Demir AS, Tanyeli C, Gulbeyaz V and Akgun H, Enantioselective synthesis of 4-Hydroxy-3-(3-Oxo-1-Phenyl Butyl)-2H-1-Benzopyran-2-One (Warfarin). Turk J Chem 20: 139-145 (1996).
    • (1996) Turk J Chem , vol.20 , pp. 139-145
    • Demir, A.S.1    Tanyeli, C.2    Gulbeyaz, V.3    Akgun, H.4
  • 34
    • 0035794284 scopus 로고    scopus 로고
    • An asymmetric approach to coumarin anticoagulants via hetero-Diels-Alder cycloaddition
    • Cravotto G, Nano GM, Palmisano G and Tagliapietra S, An asymmetric approach to coumarin anticoagulants via hetero-Diels-Alder cycloaddition. Tetrahedron Asymmetry 12: 707-709 (2001).
    • (2001) Tetrahedron Asymmetry , vol.12 , pp. 707-709
    • Cravotto, G.1    Nano, G.M.2    Palmisano, G.3    Tagliapietra, S.4
  • 35
    • 0242323633 scopus 로고    scopus 로고
    • Organocatalytic asymmetric Michael reaction of cyclic 1,3-Dicarbonyl compounds and α,β-unsaturated ketones-a highly atom-economic catalytic one-step formation of optically active warfarin anticoagulant
    • Halland N, Hansen T and Jørgensen KA, Organocatalytic asymmetric Michael reaction of cyclic 1, 3-Dicarbonyl compounds and α, β-unsaturated ketones-a highly atom-economic catalytic one-step formation of optically active warfarin anticoagulant. Angew Chem Int Ed 42: 4955-4957 (2003).
    • (2003) Angew Chem Int Ed , vol.42 , pp. 4955-4957
    • Halland, N.1    Hansen, T.2    Jørgensen, K.A.3
  • 36
    • 33847051264 scopus 로고    scopus 로고
    • Highly enantioselective Michael addition of cyclic 1,3-Dicarbonyl compounds to α,β-unsaturated ketones
    • Xie JW, Yue L, Chen W, Du W, Zhu J, Deng JG, et al, Highly enantioselective Michael addition of cyclic 1, 3-Dicarbonyl compounds to α, β-unsaturated ketones. Org Lett 9: 413-415 (2007).
    • (2007) Org Lett , vol.9 , pp. 413-415
    • Xie, J.W.1    Yue, L.2    Chen, W.3    Du, W.4    Zhu, J.5    Deng, J.G.6
  • 37
    • 33845262220 scopus 로고    scopus 로고
    • Substrate-directed stereo-selectivity in vicinal diamine-catalyzed synthesis of warfarin
    • Kim H, Yen C, Preston P and Chin J, Substrate-directed stereo-selectivity in vicinal diamine-catalyzed synthesis of warfarin. Org Lett 8: 5239-5242 (2006).
    • (2006) Org Lett , vol.8 , pp. 5239-5242
    • Kim, H.1    Yen, C.2    Preston, P.3    Chin, J.4
  • 38
    • 70350153879 scopus 로고    scopus 로고
    • Organocatalytic enantioselective Michael addition of 4-Hydroxycoumarin to α,β-unsaturated ketones: a simple synthesis of warfarin
    • Dong Z, Wang L, Chen X, Liu X, Lin L and Feng XM, Organocatalytic enantioselective Michael addition of 4-Hydroxycoumarin to α, β-unsaturated ketones: a simple synthesis of warfarin. Eur J Org Chem 2009: 5192-5197 (2009).
    • (2009) Eur J Org Chem , vol.2009 , pp. 5192-5197
    • Dong, Z.1    Wang, L.2    Chen, X.3    Liu, X.4    Lin, L.5    Feng, X.M.6
  • 39
    • 0025763437 scopus 로고
    • Enzyme catalysis: not different, just better
    • Knowles JR, Enzyme catalysis: not different, just better. Nature 350: 121-124 (1991).
    • (1991) Nature , vol.350 , pp. 121-124
    • Knowles, J.R.1
  • 41
    • 78651397152 scopus 로고    scopus 로고
    • The lipase-catalyzed asymmetric C-C Michael addition
    • Cai JF, Guan Z and He YH, The lipase-catalyzed asymmetric C-C Michael addition. J Mol Catal B: Enzym 68: 240-244 (2011).
    • (2011) J Mol Catal B: Enzym , vol.68 , pp. 240-244
    • Cai, J.F.1    Guan, Z.2    He, Y.H.3
  • 42
    • 79958001632 scopus 로고    scopus 로고
    • Acidic proteinase from Aspergillus usamii catalyzed Michael addition of ketones to nitroolefins
    • Xu KL, Guan Z and He YH, Acidic proteinase from Aspergillus usamii catalyzed Michael addition of ketones to nitroolefins. J Mol Catal B: Enzym 71: 108-112 (2011).
    • (2011) J Mol Catal B: Enzym , vol.71 , pp. 108-112
    • Xu, K.L.1    Guan, Z.2    He, Y.H.3
  • 43
    • 0037416684 scopus 로고    scopus 로고
    • Effects of water activity and alcohol concentration on the kinetic resolution of lipase-catalyzed acyl transfer in organic solvents
    • Cheng YC and Tsai SW, Effects of water activity and alcohol concentration on the kinetic resolution of lipase-catalyzed acyl transfer in organic solvents. Enzyme Microbiol Technol 32: 362-368 (2003).
    • (2003) Enzyme Microbiol Technol , vol.32 , pp. 362-368
    • Cheng, Y.C.1    Tsai, S.W.2
  • 44
    • 67849103981 scopus 로고    scopus 로고
    • Active-site motions and polarity enhance catalytic turnover of hydrated subtilisin dissolved in organic solvents
    • Hudson EP, Eppler RK, Beaudoin JM, Dordick JS, Reimer JA and Clark DS, Active-site motions and polarity enhance catalytic turnover of hydrated subtilisin dissolved in organic solvents. J Am Chem Soc 131: 4294-4300 (2009).
    • (2009) J Am Chem Soc , vol.131 , pp. 4294-4300
    • Hudson, E.P.1    Eppler, R.K.2    Beaudoin, J.M.3    Dordick, J.S.4    Reimer, J.A.5    Clark, D.S.6
  • 45
    • 34948820219 scopus 로고    scopus 로고
    • Lipase-catalyzed esterification of citronellol with lauric acid in supercritical carbon dioxide/co-solvent media
    • Habulin M, Šabeder S, Paljevac M, Primožič M and Knez Ž, Lipase-catalyzed esterification of citronellol with lauric acid in supercritical carbon dioxide/co-solvent media. J Supercrit Fluid 43: 199-203 (2007).
    • (2007) J Supercrit Fluid , vol.43 , pp. 199-203
    • Habulin, M.1    Šabeder, S.2    Paljevac, M.3    Primožič, M.4    Knez, Z.5
  • 46
    • 0021763770 scopus 로고
    • Enzymatic catalysis in organic media at 100 degrees C
    • Zaks A and Klibanov AM, Enzymatic catalysis in organic media at 100 degrees C. Science 224: 1249-1251 (1984).
    • (1984) Science , vol.224 , pp. 1249-1251
    • Zaks, A.1    Klibanov, A.M.2


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