메뉴 건너뛰기




Volumn 30, Issue 4, 2012, Pages 399-408

Decarboxylative aldol reaction catalysed by lipases and a protease in organic co-solvent mixtures and nearly anhydrous organic solvent media

Author keywords

Biocatalysis in aqueous organic co solvent mixtures; CC bond formation; Decarboxylative aldol reaction; Lipases

Indexed keywords

ALCALASE; ALDOL REACTIONS; AQUEOUS BUFFER; C-C BOND FORMATION; CANDIDA ANTARCTICA LIPASE B; CATALYSE; COSOLVENT MIXTURES; CROSS-LINKED PROTEINS; ENANTIOMERIC EXCESS; ETHYLACETOACETATE; LOW WATER; ORGANIC SOLVENT MEDIA; REACTION MEDIA; REACTION MEDIUM;

EID: 84866897120     PISSN: 10242422     EISSN: 10292446     Source Type: Journal    
DOI: 10.3109/10242422.2012.703181     Document Type: Article
Times cited : (15)

References (41)
  • 3
    • 76349094086 scopus 로고    scopus 로고
    • Environmentally benign metal free decarboxylative aldol and Mannich Reactions
    • Boudoux J, Lefebvre P, Legay R, Lasne M- C, Rouden J. 2010. Environmentally benign metal free decarboxylative aldol and Mannich Reactions. Green Chem 12: 252 - 259.
    • (2010) Green Chem , vol.12 , pp. 252-259
    • Boudoux, J.1    Lefebvre, P.2    Legay, R.3    Lasne, M.-C.4    Rouden, J.5
  • 4
    • 70350257632 scopus 로고    scopus 로고
    • Advances in enzyme immobilization
    • Brady D, Jordann J. 2009. Advances in enzyme immobilization. Biotechnol Lett 31: 1639 - 1650
    • (2009) Biotechnol Lett , vol.31 , pp. 1639-1650
    • Brady, D.1    Jordann, J.2
  • 5
    • 0026331675 scopus 로고
    • Application of industrial protease'Alcalase'in peptide synthesis
    • Chen ST, Chen SY, Hsiao CS, Wang KT. 1991. Application of industrial protease'Alcalase'in peptide synthesis. Biomed Bichem Acta 50: S181 - S186
    • (1991) Biomed Bichem Acta , vol.50
    • Chen, S.T.1    Chen, S.Y.2    Hsiao, C.S.3    Wang, K.T.4
  • 6
    • 79960820232 scopus 로고    scopus 로고
    • Bacterial degradation of strobilurin fungicides: A role for a promiscous methyl esterase activity of the subtilisin protease?
    • Clinton B, Warden AC, Haboury S, Eaaston CJ, Kotsonis S, Taylor MC, et al. 2011. Bacterial degradation of strobilurin fungicides: a role for a promiscous methyl esterase activity of the subtilisin protease? Biocatal Biotransform 29: 1 - 11.
    • (2011) Biocatal Biotransform , vol.29 , pp. 1-11
    • Clinton, B.1    Warden, A.C.2    Haboury, S.3    Eaaston, C.J.4    Kotsonis, S.5    Taylor, M.C.6
  • 8
    • 79955634803 scopus 로고    scopus 로고
    • Lipase CAL-B does not catalyze a promiscuous decarboxylative aldol addition or Knoevenagel reaction
    • Evitt AS, Bornscheuer UT. 2011. Lipase CAL-B does not catalyze a promiscuous decarboxylative aldol addition or Knoevenagel reaction. Green Chem 13: 1141 - 1142
    • (2011) Green Chem , vol.13 , pp. 1141-1142
    • Evitt, A.S.1    Bornscheuer, U.T.2
  • 9
    • 71549120756 scopus 로고    scopus 로고
    • Lipase-catalysed decarboxylative aldol reaction and decarboxylative Knoevenagel reaction
    • Feng X- W, Li C, Wang N, Li K, Zhang W- W, Wang Z, Yu X-O. 2009. Lipase-catalysed decarboxylative aldol reaction and decarboxylative Knoevenagel reaction. Green Chem 11: 1933 - 1936
    • (2009) Green Chem , vol.11 , pp. 1933-1936
    • Feng, X.-W.1    Li, C.2    Wang, N.3    Li, K.4    Zhang, W.-W.5    Wang, Z.6    Yu, X.-O.7
  • 10
    • 84891019677 scopus 로고    scopus 로고
    • Aldolases: Enzymes for making and breaking C-C bonds
    • In: Gotor V, Alfonso I, Garcia-Urdiales E, eds. Weinheim Wiley- VCH.
    • Fessner W-D. 2008. Aldolases: enzymes for making and breaking C-C bonds. In: Gotor V, Alfonso I, Garcia-Urdiales E, eds. Asymmetric organic synthesis with enzymes. Weinheim: Wiley- VCH. pp. 275 - 331.
    • (2008) Asymmetric Organic Synthesis with Enzymes , pp. 275-331
    • Fessner, W.-D.1
  • 11
    • 0026517617 scopus 로고
    • Enzyme function in organic solvents
    • Gupta MN. 1992. Enzyme function in organic solvents. Eur J Biochem 203: 25 - 32.
    • (1992) Eur J Biochem , vol.203 , pp. 25-32
    • Gupta, M.N.1
  • 13
    • 79955420122 scopus 로고    scopus 로고
    • Isozymes, moonlighting proteins and promiscous enzymes
    • Gupta MN, Kapoor M, Majumder AB, Singh V. 2011. Isozymes, moonlighting proteins and promiscous enzymes. Curr Sci 100: 1152 - 1162
    • (2011) Curr Sci , vol.100 , pp. 1152-1162
    • Gupta, M.N.1    Kapoor, M.2    Majumder, A.B.3    Singh, V.4
  • 14
    • 34247131307 scopus 로고    scopus 로고
    • Enzyme promiscuity: Mechanism and applications
    • Hult K, Berglund P. 2007. Enzyme promiscuity: mechanism and applications. Trends Biotechnol 25: 231 - 238.
    • (2007) Trends Biotechnol , vol.25 , pp. 231-238
    • Hult, K.1    Berglund, P.2
  • 15
    • 17444384812 scopus 로고    scopus 로고
    • A microwave assisted microassay for lipase
    • Jain S, Jain S, Gupta MN. 2005. A microwave assisted microassay for lipase. Anal Bioanal Chem 381: 1480 - 1482
    • (2005) Anal Bioanal Chem , vol.381 , pp. 1480-1482
    • Jain, S.1    Jain, S.2    Gupta, M.N.3
  • 16
    • 84858071530 scopus 로고    scopus 로고
    • Lipase promiscuity and its biochemical applications
    • Kapoor M, Gupta MN. 2012. Lipase promiscuity and its biochemical applications. Process Biochem 47: 555 - 569.
    • (2012) Process Biochem , vol.47 , pp. 555-569
    • Kapoor, M.1    Gupta, M.N.2
  • 17
    • 77953623874 scopus 로고    scopus 로고
    • Enzyme promiscuity: A mechanistic and evolutionary perspective
    • Khersonsky O, Tawfik DS. 2010. Enzyme promiscuity: a mechanistic and evolutionary perspective. Annu Rev Biochem 79: 471 - 505.
    • (2010) Annu Rev Biochem , vol.79 , pp. 471-505
    • Khersonsky, O.1    Tawfik, D.S.2
  • 19
    • 0025882622 scopus 로고
    • Denaturation capacity: A new quantitative criterion for selection of organic solvents as reaction media in biocatalysis
    • Khmelnitsky YL, Mozhaev VV, Belova AB, Sergeeva MV, Martinek K. 1991. Denaturation capacity: a new quantitative criterion for selection of organic solvents as reaction media in biocatalysis. Eur J Biochem 198: 31 - 41.
    • (1991) Eur J Biochem , vol.198 , pp. 31-41
    • Khmelnitsky, Y.L.1    Mozhaev, V.V.2    Belova, A.B.3    Sergeeva, M.V.4    Martinek, K.5
  • 20
    • 0036327837 scopus 로고    scopus 로고
    • Lipases from Candida antarctica: Unique biocatalysts from a unique origin
    • Kirk O, Christensen MW. 2002. Lipases from Candida antarctica: unique biocatalysts from a unique origin. Org Process Res Dev 6: 446 - 451.
    • (2002) Org Process Res Dev , vol.6 , pp. 446-451
    • Kirk, O.1    Christensen, M.W.2
  • 21
    • 0037189273 scopus 로고    scopus 로고
    • A new protocol for a regioselective aldol condensation as an alternative convenient synthesis of β -ketols and α, β -unsaturated ketones
    • Kourouli T, Kefalas P, Ragoussis N, Ragoussis V. 2002. A new protocol for a regioselective aldol condensation as an alternative convenient synthesis of β -ketols and α, β -unsaturated ketones. J Org Chem 67: 4615 - 4618
    • (2002) J Org Chem , vol.67 , pp. 4615-4618
    • Kourouli, T.1    Kefalas, P.2    Ragoussis, N.3    Ragoussis, V.4
  • 22
    • 0035927926 scopus 로고    scopus 로고
    • Enzyme-coated microcrystals: A 1-step method for high activity biocatalyst preparation
    • Kreiner M, Moore BD, Parker MC. 2001. Enzyme-coated microcrystals: a 1-step method for high activity biocatalyst preparation . Chem Commun 1096 - 1097
    • (2001) Chem Commun , pp. 1096-1097
    • Kreiner, M.1    Moore, B.D.2    Parker, M.C.3
  • 23
    • 0002018112 scopus 로고
    • Medium-Engineering for bio-organic synthesis
    • Laane C. 1987. Medium-Engineering for bio-organic synthesis. Biocatalysis 1: 17 - 22.
    • (1987) Biocatalysis , vol.1 , pp. 17-22
    • Laane, C.1
  • 24
    • 44649139781 scopus 로고    scopus 로고
    • Biocatalytic promiscuity: The fi rst lipase c atalysed asymmetric aldol reaction
    • Li C, Feng X- W, Wang N, Zhou Y- J, Yu X-O. 2009a. Biocatalytic promiscuity: the fi rst lipase c atalysed asymmetric aldol reaction. Green Chem 11: 616 - 618.
    • (2009) Green Chem , vol.11 , pp. 616-618
    • Li, C.1    Feng, X.-W.2    Wang, N.3    Zhou, Y.-J.4    Yu, X.-O.5
  • 25
    • 67649114374 scopus 로고    scopus 로고
    • Lipasecatalysed 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 X-W, Wang N, Yu X-O. 2009b. Lipasecatalysed direct Mannich reaction in water: utilization of biocatalytic promiscuity for C - C bond formation in a'one-pot'synthesis. Green Chem 11: 777 - 779.
    • (2009) Green Chem , vol.11 , pp. 777-779
    • Li, K.1    He, T.2    Li, C.3    Feng, X.-W.4    Wang, N.5    Yu, X.-O.6
  • 26
    • 78649447899 scopus 로고    scopus 로고
    • Promiscuous protease-catalyzed aldol reactions: A facile biocatalytic protocol for carbon-carbon bond formation in aqueous media
    • Li C, Zhou Y-J, Wang N, Feng X- W, Li K, Yu X-O. 2010. Promiscuous protease-catalyzed aldol reactions: a facile biocatalytic protocol for carbon-carbon bond formation in aqueous media. J Biotechnol 15: 539 - 545.
    • (2010) J Biotechnol , vol.15 , pp. 539-545
    • Li, C.1    Zhou, Y.-J.2    Wang, N.3    Feng, X.-W.4    Li, K.5    Yu, X.-O.6
  • 28
    • 82355191999 scopus 로고    scopus 로고
    • Increasing the catalytic effi - Ciency of Candida rugosa lipase for the synthesis of tert-alkyl butyrates in low-water media
    • Majumder AB, Gupta MN. 2011. Increasing the catalytic effi - ciency of Candida rugosa lipase for the synthesis of tert-alkyl butyrates in low-water media. Biocatal.Biotransform 29: 238 - 245.
    • (2011) Biocatal.Biotransform , vol.29 , pp. 238-245
    • Majumder, A.B.1    Gupta, M.N.2
  • 29
    • 67650909388 scopus 로고    scopus 로고
    • Lipase catalyzed condensation reaction with a tricyclic diketone-yet another example of biocatalytic promiscuity
    • Majumder AB, Ramesh NG, Gupta MN. 2009. Lipase catalyzed condensation reaction with a tricyclic diketone-yet another example of biocatalytic promiscuity. Tetrahedron Lett 50: 5190 - 5193
    • (2009) Tetrahedron Lett , vol.50 , pp. 5190-5193
    • Majumder, A.B.1    Ramesh, N.G.2    Gupta, M.N.3
  • 30
    • 30344476991 scopus 로고    scopus 로고
    • Enhancing the synthetic utility of aldolase antibody 38C2
    • Mondal K, Ramesh NG, Roy I, Gupta MN. 2006. Enhancing the synthetic utility of aldolase antibody 38C2. Bioorg Med Chem Lett 16: 807 - 810.
    • (2006) Bioorg Med Chem Lett , vol.16 , pp. 807-810
    • Mondal, K.1    Ramesh, N.G.2    Roy, I.3    Gupta, M.N.4
  • 32
    • 0842326656 scopus 로고    scopus 로고
    • Cu(II)-catalyzed enantioselective aldol condensation between malonic acid hemithioesters and aldehydes
    • Orlandi S, Benaglia M, Cozzi F. 2004. Cu(II)-catalyzed enantioselective aldol condensation between malonic acid hemithioesters and aldehydes. Tetrahedron Lett 45: 1747 - 1749
    • (2004) Tetrahedron Lett , vol.45 , pp. 1747-1749
    • Orlandi, S.1    Benaglia, M.2    Cozzi, F.3
  • 33
    • 54749090797 scopus 로고    scopus 로고
    • Lipases enantioselectivity alteration by immobilization techniques
    • Palomo JM. 2008. Lipases enantioselectivity alteration by immobilization techniques. Curr Bioact Compd 4: 126 - 138.
    • (2008) Curr Bioact Compd , vol.4 , pp. 126-138
    • Palomo, J.M.1
  • 34
    • 65949091574 scopus 로고    scopus 로고
    • Modulation of enzyme selectivity via immobilization
    • Palomo JM. 2009. Modulation of enzyme selectivity via immobilization . Curr Org Synth 6: 1 - 14.
    • (2009) Curr Org Synth , vol.6 , pp. 1-14
    • Palomo, J.M.1
  • 35
    • 0002662732 scopus 로고    scopus 로고
    • Enhancement of Candida antarctica lipase B enantioselectivity and activity in organic solvent
    • Parker M-C, Brown SA, Robertson L, Turner NJ. 1998. Enhancement of Candida antarctica lipase B enantioselectivity and activity in organic solvent. Chem Commun 2247 - 2248
    • (1998) Chem Commun , pp. 2247-2248
    • Parker, M.-C.1    Brown, S.A.2    Robertson, L.3    Turner, N.J.4
  • 36
    • 35348850061 scopus 로고    scopus 로고
    • Highly stereoselective direct aldol reactions catalyzed by (S)-NOBIN-l-prolinamide
    • Russo A, Botta G, Lattanzi A. 2007. Highly stereoselective direct aldol reactions catalyzed by (S)-NOBIN-l-prolinamide. Tetrahedron 63: 11886 - 11892.
    • (2007) Tetrahedron , vol.63 , pp. 11886-11892
    • Russo, A.1    Botta, G.2    Lattanzi, A.3
  • 37
    • 0030800148 scopus 로고    scopus 로고
    • Enhancement of the enantioselectivity in lipase catalysed kinetic resolutions of 3-Phenyl-2H-azirine-2-methanol by lowering the temperature to 2034; 40 °c
    • Sakai T, Kawabata T, Ema T, Utaka M. 1997. Enhancement of the enantioselectivity in lipase catalysed kinetic resolutions of 3-Phenyl-2H-azirine-2-methanol by lowering the temperature to 2034; 40 °C. J Org Chem 62: 4906 - 4907
    • (1997) J Org Chem , vol.62 , pp. 4906-4907
    • Sakai, T.1    Kawabata, T.2    Ema, T.3    Utaka, M.4
  • 38
    • 33846642511 scopus 로고    scopus 로고
    • Kinetic resolution of (≲πλθσμν∀)- 1- phenylethanol in [Bmim][PF6] using high activity preparations of lipases
    • Shah S, Gupta MN. 2007. Kinetic resolution of (≲πλθ σμν∀)-1- phenylethanol in [Bmim][PF6] using high activity preparations of lipases. Bioorg Med Chem Lett 17: 921 - 924.
    • (2007) Bioorg Med Chem Lett , vol.17 , pp. 921-924
    • Shah, S.1    Gupta, M.N.2
  • 39
    • 45849113968 scopus 로고    scopus 로고
    • Cross-linked protein-coated microcrystals as biocatalysts in non-aqueous solvents
    • Shah S, Sharma A, Gupta MN. 2008. Cross-linked protein-coated microcrystals as biocatalysts in non-aqueous solvents. Biocatal Biotransform 26: 266 - 271.
    • (2008) Biocatal Biotransform , vol.26 , pp. 266-271
    • Shah, S.1    Sharma, A.2    Gupta, M.N.3
  • 40
    • 5644293379 scopus 로고    scopus 로고
    • Process intensifi cation with biocatalysts: Dynamic kinetic resolution and fl uorous phase switch with continuous extraction
    • Teo E-L, Chuah G-K, Huguet ARJ, Jaenicke S, Pande G, Zhu Y. 2004. Process intensifi cation with biocatalysts: dynamic kinetic resolution and fl uorous phase switch with continuous extraction . Catal today 97: 263 - 270.
    • (2004) Catal Today , vol.97 , pp. 263-270
    • Teo, E.-L.1    Chuah, G.-K.2    Arj, H.3    Jaenicke, S.4    Pande, G.5    Zhu, Y.6
  • 41
    • 4344647097 scopus 로고    scopus 로고
    • Lipase catalysed Michael addition of secondary amines to acrylonitrile
    • Torre O, Alfonso I, Gotor V. 2004. Lipase catalysed Michael addition of secondary amines to acrylonitrile. Chem Commun 1724 - 1725.
    • (2004) Chem Commun , pp. 1724-1725
    • Torre, O.1    Alfonso, I.2    Gotor, V.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.