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Volumn 10, Issue 2, 1999, Pages 130-136

Combinatorial biocatalysis: Taking the lead from Nature

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME; RECOMBINANT ENZYME;

EID: 0032995634     PISSN: 09581669     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0958-1669(99)80022-6     Document Type: Article
Times cited : (51)

References (23)
  • 1
    • 0002587387 scopus 로고    scopus 로고
    • Generation of solution-phase libraries of organic molecules by combinatorial biocatalysis
    • I.M. Chaiken, & K.D. Janda. Washington DC: ACS. This original publication on combinatorial biocatalysis focuses on libraries generated by extensive derivatization of three small lead molecules. The range and extent of biotransformations included in the derivatization process is without precedent. Further application of combinatorial biocatalysis to modification of the antimitotic agent paclitaxel is also reported.
    • Khmelnitsky Y.L., Michels P.C., Dordick J.S., Clark D.S. Generation of solution-phase libraries of organic molecules by combinatorial biocatalysis. Chaiken I.M., Janda K.D. ACS Symposium Series. 1996;144-157 ACS, Washington DC. This original publication on combinatorial biocatalysis focuses on libraries generated by extensive derivatization of three small lead molecules. The range and extent of biotransformations included in the derivatization process is without precedent. Further application of combinatorial biocatalysis to modification of the antimitotic agent paclitaxel is also reported.
    • (1996) ACS Symposium Series , pp. 144-157
    • Khmelnitsky, Y.L.1    Michels, P.C.2    Dordick, J.S.3    Clark, D.S.4
  • 2
    • 0032404543 scopus 로고    scopus 로고
    • Combinatorial biocatalysis: A natural approach to drug discovery
    • A bergenin library containing 600 new derivatives is generated in an automated two-step synthesis involving independent biotransformations by 16 purified enzymes and 25 microorganisms. The role of nonaqueous biocatalysis and a regioselective combinatorial acylation of dihydroxytropane are also presented.
    • Michels P.C., Khmelnitsky Y.L., Dordick J.S., Clark D.S. Combinatorial biocatalysis: a natural approach to drug discovery. Trends Biotechnol. 16:1998;210-215. A bergenin library containing 600 new derivatives is generated in an automated two-step synthesis involving independent biotransformations by 16 purified enzymes and 25 microorganisms. The role of nonaqueous biocatalysis and a regioselective combinatorial acylation of dihydroxytropane are also presented.
    • (1998) Trends Biotechnol , vol.16 , pp. 210-215
    • Michels, P.C.1    Khmelnitsky, Y.L.2    Dordick, J.S.3    Clark, D.S.4
  • 3
    • 0030938870 scopus 로고    scopus 로고
    • The utility of enzymes in generating molecular diversity. Lipase mediated amidation of polybenzyl esters
    • An amide library is synthesized in an nonaqueous one-pot method, demonstrating that the broad specificity of the P. cepacia lipase lends itself to facile library synthesis.
    • Adamczyk M., Gebler J.C., Grote J. The utility of enzymes in generating molecular diversity. Lipase mediated amidation of polybenzyl esters. Bioorg Med Chem Lett. 8:1997;1027-1030. An amide library is synthesized in an nonaqueous one-pot method, demonstrating that the broad specificity of the P. cepacia lipase lends itself to facile library synthesis.
    • (1997) Bioorg Med Chem Lett , vol.8 , pp. 1027-1030
    • Adamczyk, M.1    Gebler, J.C.2    Grote, J.3
  • 5
    • 0031587450 scopus 로고    scopus 로고
    • Synthesis of water-soluble paclitaxel derivatives by enzymatic acylation
    • Thermolysin-catalyzed acylation was followed by Candida antarctica lipase hydrolysis or transesterification to yield a library of paclitaxel derivatives. The first publication of nonaqueous enzymology applied to a taxane.
    • Khmelnitsky Y.L., Budde C., Arnold J.M., Usyatinsky A., Clark D.S., Dordick J.S. Synthesis of water-soluble paclitaxel derivatives by enzymatic acylation. J Am Chem Soc. 119:1997;11554-11555. Thermolysin-catalyzed acylation was followed by Candida antarctica lipase hydrolysis or transesterification to yield a library of paclitaxel derivatives. The first publication of nonaqueous enzymology applied to a taxane.
    • (1997) J Am Chem Soc , vol.119 , pp. 11554-11555
    • Khmelnitsky, Y.L.1    Budde, C.2    Arnold, J.M.3    Usyatinsky, A.4    Clark, D.S.5    Dordick, J.S.6
  • 6
    • 0032537029 scopus 로고    scopus 로고
    • Regioselective enzymatic acylation as a tool for producing solution-phase combinatorial libraries
    • Bergenin is used as a model to demonstrate how biocatalysts of differing regioselectivity can be used to generate combinatorial libraries. Without the aid of protection chemistry, it is shown that biocatalysts can be used to exercise precise control over the derivatization of polyfunctional molecules. High-throughput automation of combinatorial biocatalysis is discussed in detail for the first time.
    • Mozahaev V.V., Budde C.L., Rich J.O., Ustatinsky A.Y., Michels P.C., Khmelnitsky Y.L., Clark D.S., Dordick J.S. Regioselective enzymatic acylation as a tool for producing solution-phase combinatorial libraries. Tetrahedron. 54:1998;3971-3982. Bergenin is used as a model to demonstrate how biocatalysts of differing regioselectivity can be used to generate combinatorial libraries. Without the aid of protection chemistry, it is shown that biocatalysts can be used to exercise precise control over the derivatization of polyfunctional molecules. High-throughput automation of combinatorial biocatalysis is discussed in detail for the first time.
    • (1998) Tetrahedron , vol.54 , pp. 3971-3982
    • Mozahaev, V.V.1    Budde, C.L.2    Rich, J.O.3    Ustatinsky, A.Y.4    Michels, P.C.5    Khmelnitsky, Y.L.6    Clark, D.S.7    Dordick, J.S.8
  • 7
    • 0032082486 scopus 로고    scopus 로고
    • The evolution of biotransformation technologies
    • This recent review provides a perspective as to the key areas of current research and developments in biotransformations.
    • Dordick J.S., Khmelnitsky Y.L., Sergeeva M.V. The evolution of biotransformation technologies. Curr Opin Microbiol. 1:1998;311-318. This recent review provides a perspective as to the key areas of current research and developments in biotransformations.
    • (1998) Curr Opin Microbiol , vol.1 , pp. 311-318
    • Dordick, J.S.1    Khmelnitsky, Y.L.2    Sergeeva, M.V.3
  • 8
    • 0031994482 scopus 로고    scopus 로고
    • Enzymes and protecting group chemistry
    • The roles of enzymes in protecting group techniques are critically reviewed with emphasis on recent achievements.
    • Pathak T., Waldmann H. Enzymes and protecting group chemistry. Curr Opin Chem Biol. 1:1998;112-120. The roles of enzymes in protecting group techniques are critically reviewed with emphasis on recent achievements.
    • (1998) Curr Opin Chem Biol , vol.1 , pp. 112-120
    • Pathak, T.1    Waldmann, H.2
  • 9
    • 0031395372 scopus 로고    scopus 로고
    • High performance polymer supports for enzyme-assisted synthesis of glycoconjugates
    • Glycosyl transferases are used to elongate glycopolymers attached to water-soluble polymer supports. Cleavage of the oligosaccharides from the polymer supports was achieved by α-chymotrypsin-catalyzed hydrolysis at an l-phenylalanine residue in the polymer primer.
    • Yamada K., Fujita E., Nishimura S.I. High performance polymer supports for enzyme-assisted synthesis of glycoconjugates. Carbohydr Res. 305:1998;443-461. Glycosyl transferases are used to elongate glycopolymers attached to water-soluble polymer supports. Cleavage of the oligosaccharides from the polymer supports was achieved by α-chymotrypsin-catalyzed hydrolysis at an l-phenylalanine residue in the polymer primer.
    • (1998) Carbohydr Res , vol.305 , pp. 443-461
    • Yamada, K.1    Fujita, E.2    Nishimura, S.I.3
  • 10
    • 0007961141 scopus 로고    scopus 로고
    • The application of enzymes in the synthesis of amino acids, peptides and carbohydrates
    • An overview of enzymes in oligomer synthesis including promising innovations such as enzyme-cleaved solid-phase linkers. Whereas the α-chymotrypsin and phosphodiesterase methods of cleavage leave linker residues on the product, the penicillin acylase route yields traceless products.
    • Turner N.J. The application of enzymes in the synthesis of amino acids, peptides and carbohydrates. Curr Org Chem. 1:1997;21-36. An overview of enzymes in oligomer synthesis including promising innovations such as enzyme-cleaved solid-phase linkers. Whereas the α-chymotrypsin and phosphodiesterase methods of cleavage leave linker residues on the product, the penicillin acylase route yields traceless products.
    • (1997) Curr Org Chem , vol.1 , pp. 21-36
    • Turner, N.J.1
  • 11
    • 0032551298 scopus 로고    scopus 로고
    • Testing for diffusion limitation in salt-activated enzyme catalysts in organic solvents
    • Bedell D.A., Mozahaev V.V., Clark D.S., Dordick J.S. Testing for diffusion limitation in salt-activated enzyme catalysts in organic solvents. Biotechnol Bioeng. 6:1998;654-657.
    • (1998) Biotechnol Bioeng , vol.6 , pp. 654-657
    • Bedell, D.A.1    Mozahaev, V.V.2    Clark, D.S.3    Dordick, J.S.4
  • 12
    • 0033586738 scopus 로고    scopus 로고
    • Optimizing the salt-induced activation of enzymes in organic solvents: Effects of lyophilization time and water content
    • The specific activity of S. Carlsberg is increased by an unprecedented 20,000-fold in nonaqueous solvents following lyophilization from a buffer with high KCl content.
    • Ru M.T., Dordick J.S., Reimer J.A., Clark D.S. Optimizing the salt-induced activation of enzymes in organic solvents: effects of lyophilization time and water content. Biotechnol Bioeng. 6:1998;233-241. The specific activity of S. Carlsberg is increased by an unprecedented 20,000-fold in nonaqueous solvents following lyophilization from a buffer with high KCl content.
    • (1998) Biotechnol Bioeng , vol.6 , pp. 233-241
    • Ru, M.T.1    Dordick, J.S.2    Reimer, J.A.3    Clark, D.S.4
  • 13
    • 0031081342 scopus 로고    scopus 로고
    • Lipid coated enzymes as efficient catalysts in organic media
    • The native structure of lipases, β-galactosidases, and catalytic antibodies are presumed to be preserved when lipid complexes solubilize these biocatalysts and enhance their activity in a range of organic solvents.
    • Okahata Y., Mori T. Lipid coated enzymes as efficient catalysts in organic media. Trends Biotechnol. 15:1997;50-54. The native structure of lipases, β-galactosidases, and catalytic antibodies are presumed to be preserved when lipid complexes solubilize these biocatalysts and enhance their activity in a range of organic solvents.
    • (1997) Trends Biotechnol , vol.15 , pp. 50-54
    • Okahata, Y.1    Mori, T.2
  • 14
    • 0031240060 scopus 로고    scopus 로고
    • Application of novel preparation method for surfactant-protease complexes catalytically active in organic media
    • Okazaki S.Y., Kamiya N., Goto M. Application of novel preparation method for surfactant-protease complexes catalytically active in organic media. Biotechnol Prog. 13:1997;551-556.
    • (1997) Biotechnol Prog , vol.13 , pp. 551-556
    • Okazaki, S.Y.1    Kamiya, N.2    Goto, M.3
  • 15
    • 0031047280 scopus 로고    scopus 로고
    • Structure and function of subtilisin BPN′ solubilized in organic solvents
    • The remarkable activity of subtilisin BPN′ solubilized by Aerosol OT ion pairing is investigated with respect to its structure in organic solvents. Ion pairing is shown to partially preserve the flexibility of the enzyme in octane. In addition to enhanced activity and stability, it is shown for the first time that ion-paired enzymes can be renatured in an organic solvent, octane, after thermal- or tetrahydrofuran-induced denaturation.
    • Wangikar P.P., Michels P.C., Clark D.S., Dordick J.S. Structure and function of subtilisin BPN′ solubilized in organic solvents. J Am Chem Soc. 119:1997;70-76. The remarkable activity of subtilisin BPN′ solubilized by Aerosol OT ion pairing is investigated with respect to its structure in organic solvents. Ion pairing is shown to partially preserve the flexibility of the enzyme in octane. In addition to enhanced activity and stability, it is shown for the first time that ion-paired enzymes can be renatured in an organic solvent, octane, after thermal- or tetrahydrofuran-induced denaturation.
    • (1997) J Am Chem Soc , vol.119 , pp. 70-76
    • Wangikar, P.P.1    Michels, P.C.2    Clark, D.S.3    Dordick, J.S.4
  • 16
    • 0029887937 scopus 로고    scopus 로고
    • Generation of soluble and active subtilisin and alpha-chymotrypsin in organic solvents via hydrophobic ion pairing
    • Myer J.D., Kendrick B.S., Matsura J.E., Ruth J.A., Bryan P.N., Manning M.C. Generation of soluble and active subtilisin and alpha-chymotrypsin in organic solvents via hydrophobic ion pairing. Int J Peptide Protein Res. 3:1996;177-181.
    • (1996) Int J Peptide Protein Res , vol.3 , pp. 177-181
    • Myer, J.D.1    Kendrick, B.S.2    Matsura, J.E.3    Ruth, J.A.4    Bryan, P.N.5    Manning, M.C.6
  • 17
    • 0032510667 scopus 로고    scopus 로고
    • Directed evolution of an aspartate aminotransferase with new substrate specificities
    • Underutilized due to their characteristically exclusive specificity aminotransferases have great synthetic potential. Directed evolution is used to alter the specificity of an aspartate aminotransferase, resulting in a 105-fold increase in catalytic efficiency for novel substrates.
    • Yano T., Oue S., Kagamiyama H. Directed evolution of an aspartate aminotransferase with new substrate specificities. Proc Natl Acad Sci USA. 95:1998;5511-5515. Underutilized due to their characteristically exclusive specificity aminotransferases have great synthetic potential. Directed evolution is used to alter the specificity of an aspartate aminotransferase, resulting in a 105-fold increase in catalytic efficiency for novel substrates.
    • (1998) Proc Natl Acad Sci USA , vol.95 , pp. 5511-5515
    • Yano, T.1    Oue, S.2    Kagamiyama, H.3
  • 18
    • 0030989062 scopus 로고    scopus 로고
    • Directed evolution of a fucosidase from a galactosidase by DNA shuffling and screening
    • Seven rounds of DNA shuffling from Escherichia coli lacZ β-galactosidase produced an enzyme with 1,000-fold higher specificity toward o-nitrophenyl fucopyranoside versus o-nitrophenyl galactopyranoside. The scarcity of β-fucosidases in Nature underscores the importance of this work as an example of how directed evolution can provide novel enzymes of synthetic utility.
    • Zhang J.H., Dawes G., Stemmer W.P.C. Directed evolution of a fucosidase from a galactosidase by DNA shuffling and screening. Proc Natl Acad Sci USA. 94:1997;4504-4509. Seven rounds of DNA shuffling from Escherichia coli lacZ β-galactosidase produced an enzyme with 1,000-fold higher specificity toward o-nitrophenyl fucopyranoside versus o-nitrophenyl galactopyranoside. The scarcity of β-fucosidases in Nature underscores the importance of this work as an example of how directed evolution can provide novel enzymes of synthetic utility.
    • (1997) Proc Natl Acad Sci USA , vol.94 , pp. 4504-4509
    • Zhang, J.H.1    Dawes, G.2    Stemmer, W.P.C.3
  • 19
    • 0031543435 scopus 로고    scopus 로고
    • Directed evolution of enzyme catalysts
    • The evolution of enzymes with improved thermostability, improved stability in artificial environments, altered substrate specificity, and enhanced enantioselectivity are critically presented along with discussion and analysis of strategies for directed evolution.
    • Kuchner O., Arnold F.H. Directed evolution of enzyme catalysts. Trends Biotechnol. 12:1997;523-530. The evolution of enzymes with improved thermostability, improved stability in artificial environments, altered substrate specificity, and enhanced enantioselectivity are critically presented along with discussion and analysis of strategies for directed evolution.
    • (1997) Trends Biotechnol , vol.12 , pp. 523-530
    • Kuchner, O.1    Arnold, F.H.2
  • 20
    • 0001270261 scopus 로고    scopus 로고
    • Design by directed evolution
    • Arnold F.H. Design by directed evolution. Accounts Chem Res. 31:1998;125-131.
    • (1998) Accounts Chem Res , vol.31 , pp. 125-131
    • Arnold, F.H.1
  • 22
    • 0032424429 scopus 로고    scopus 로고
    • Bringing biological solutions to chemical problems
    • This commentary reviews the status of catalytic antibodies and provides perspective on their importance in future synthetic applications.
    • Schultz P. Bringing biological solutions to chemical problems. Proc Natl Acad Sci USA. 95:1998;14590-14591. This commentary reviews the status of catalytic antibodies and provides perspective on their importance in future synthetic applications.
    • (1998) Proc Natl Acad Sci USA , vol.95 , pp. 14590-14591
    • Schultz, P.1
  • 23
    • 0032426662 scopus 로고    scopus 로고
    • The antibody catalysis route to the total synthesis of epothilones
    • Harnessing catalytic antibodies with valuable aldolase activity, the stereoselective synthesis of natural cytotoxic agents, epothilones, demonstrates the great potential of this new class of biocatalysts.
    • Sinha S., Barbas C., Lerner R. The antibody catalysis route to the total synthesis of epothilones. Proc Natl Acad Sci USA. 95:1998;14603-14608. Harnessing catalytic antibodies with valuable aldolase activity, the stereoselective synthesis of natural cytotoxic agents, epothilones, demonstrates the great potential of this new class of biocatalysts.
    • (1998) Proc Natl Acad Sci USA , vol.95 , pp. 14603-14608
    • Sinha, S.1    Barbas, C.2    Lerner, R.3


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