메뉴 건너뛰기




Volumn 7, Issue 3, 2003, Pages 409-419

The discovery of catalytically active peptides through combinatorial chemistry

Author keywords

[No Author keywords available]

Indexed keywords

2 ACETAMINOCYCLOHEXANOL; 4 NITROPHENYL ACETATE; ACETIC ACID DERIVATIVE; ALPHA AMINO ACID; ESTER; ESTERASE; HEXANOL; HISTIDINE; IMIDE; IMINE; INOSITOL; METAL; OLIGOPEPTIDE; PEPTIDE; PEPTIDE DERIVATIVE; PEPTIDOSTEROID; PHOSPHATE; RECOMBINANT ENZYME; SERINE PROTEINASE; UNCLASSIFIED DRUG;

EID: 0037523450     PISSN: 13675931     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1367-5931(03)00065-6     Document Type: Review
Times cited : (78)

References (43)
  • 1
    • 0036739952 scopus 로고    scopus 로고
    • On inventing reactions for atom economy
    • Trost B.M. On inventing reactions for atom economy. Acc Chem Res. 35:2002;695-705.
    • (2002) Acc Chem Res , vol.35 , pp. 695-705
    • Trost, B.M.1
  • 2
    • 0026418434 scopus 로고
    • The atom economy: A search for synthetic efficiency
    • Trost B.M. The atom economy: a search for synthetic efficiency. Science. 254:1991;1471-1477.
    • (1991) Science , vol.254 , pp. 1471-1477
    • Trost, B.M.1
  • 3
    • 0035477024 scopus 로고    scopus 로고
    • Directed evolution of an enantioselective enzyme through combinatorial multiple-cassette mutagenesis
    • Reetz M.T., Wilensek S., Zha D., Jaeger K.-E. Directed evolution of an enantioselective enzyme through combinatorial multiple-cassette mutagenesis. Angew Chem Int Ed Engl. 40:2001;3589-3591.
    • (2001) Angew Chem Int Ed Engl , vol.40 , pp. 3589-3591
    • Reetz, M.T.1    Wilensek, S.2    Zha, D.3    Jaeger, K.-E.4
  • 5
    • 0037025911 scopus 로고    scopus 로고
    • Directed evolution of selective enzymes and hybrid catalysts
    • Reetz M.T. Directed evolution of selective enzymes and hybrid catalysts. Tetrahedron. 58:2002;6595-6602.
    • (2002) Tetrahedron , vol.58 , pp. 6595-6602
    • Reetz, M.T.1
  • 6
    • 0033976143 scopus 로고    scopus 로고
    • Directed evolution of enantioselective enzymes for organic chemistry
    • Jaeger K.-E., Reetz M.T. Directed evolution of enantioselective enzymes for organic chemistry. Curr Opin Chem Biol. 4:2000;68-73.
    • (2000) Curr Opin Chem Biol , vol.4 , pp. 68-73
    • Jaeger, K.-E.1    Reetz, M.T.2
  • 7
    • 0037170944 scopus 로고    scopus 로고
    • Amino acids and peptides as asymmetric organocatalysts
    • Jarvo E.R., Miller S.J. Amino acids and peptides as asymmetric organocatalysts. Tetrahedron. 58:2002;2481-2495.
    • (2002) Tetrahedron , vol.58 , pp. 2481-2495
    • Jarvo, E.R.1    Miller, S.J.2
  • 9
    • 18744388834 scopus 로고    scopus 로고
    • Evaluation of a two-stage screening procedure in the combinatorial search for serine protease-like activity
    • The above two articles describe a truely combinatorial approach to the problem of artficial, biomimetic esterase activity. The authors were able to identify - by bulk screening and recursive deconvolution - peptidosteroid structures in which both the formation and the hydrolysis of the so-called acyl-intermediate of serine hydrolases is accelerated
    • Madder A., Li L., De Muynck H., Farcy N., Van Haver D., Fant F., Vanhoenacker G., Sandra P., Davis A.P., De Clercq P.J. Evaluation of a two-stage screening procedure in the combinatorial search for serine protease-like activity. J Comb Chem. 4:2002;552-562 The above two articles describe a truely combinatorial approach to the problem of artficial, biomimetic esterase activity. The authors were able to identify - by bulk screening and recursive deconvolution - peptidosteroid structures in which both the formation and the hydrolysis of the so-called acyl-intermediate of serine hydrolases is accelerated.
    • (2002) J Comb Chem , vol.4 , pp. 552-562
    • Madder, A.1    Li, L.2    De Muynck, H.3    Farcy, N.4    Van Haver, D.5    Fant, F.6    Vanhoenacker, G.7    Sandra, P.8    Davis, A.P.9    De Clercq, P.J.10
  • 10
    • 0344428136 scopus 로고    scopus 로고
    • Discovery of peptide-zirconium complexes that mediate phosphate hydrolysis by batch screening of a combinatorial undecapeptide library
    • Berkessel A., Hérault D.A. Discovery of peptide-zirconium complexes that mediate phosphate hydrolysis by batch screening of a combinatorial undecapeptide library. Angew Chem Int Ed Engl. 38:1999;102-105.
    • (1999) Angew Chem Int Ed Engl , vol.38 , pp. 102-105
    • Berkessel, A.1    Hérault, D.A.2
  • 11
    • 0001708325 scopus 로고    scopus 로고
    • Combinatorial de novo synthesis of catalysts: How much of a hit-structure is needed for activity?
    • Two novel assays for the site-selective bulk screening of combinatorial libraries for phosphodiester cleavage are presented. The oligopeptide hits discovered in this study were analyzed for the minimal catalytically active substructure, the 'minimal catalophore'. It was found in one example that just a fraction of the overall structure was sufficient for catalytic activity. This result raises the question whether there may be other oligomeric catalysts that can be truncated to the 'minimal catalophore'
    • Berkessel A., Riedl R. Combinatorial de novo synthesis of catalysts: how much of a hit-structure is needed for activity? J Comb Chem. 2:2000;215-219 Two novel assays for the site-selective bulk screening of combinatorial libraries for phosphodiester cleavage are presented. The oligopeptide hits discovered in this study were analyzed for the minimal catalytically active substructure, the 'minimal catalophore'. It was found in one example that just a fraction of the overall structure was sufficient for catalytic activity. This result raises the question whether there may be other oligomeric catalysts that can be truncated to the 'minimal catalophore'.
    • (2000) J Comb Chem , vol.2 , pp. 215-219
    • Berkessel, A.1    Riedl, R.2
  • 12
    • 0035886866 scopus 로고    scopus 로고
    • A new screen for combinatorial catalysis; On-bead testing in agarose gel
    • This article describes the use of agarose gels for the immobilization of bead-bound libraries. As a result, site-selective detection of hydrolase activity becomes possible by a pH-sensitive probe present in the gel
    • Müller M., Mathers T.W., Davis A.P. A new screen for combinatorial catalysis; on-bead testing in agarose gel. Angew Chem Int Ed Engl. 40:2001;3813-3815 This article describes the use of agarose gels for the immobilization of bead-bound libraries. As a result, site-selective detection of hydrolase activity becomes possible by a pH-sensitive probe present in the gel.
    • (2001) Angew Chem Int Ed Engl , vol.40 , pp. 3813-3815
    • Müller, M.1    Mathers, T.W.2    Davis, A.P.3
  • 13
    • 84985609389 scopus 로고
    • Synthetic enzyme: Highly stereoselective epoxidation of chalcone in the three-phase system toluene-water-poly-(S)-alanine
    • Juliá S., Masana J., Vega J.C. Synthetic enzyme: highly stereoselective epoxidation of chalcone in the three-phase system toluene-water-poly-(S)-alanine. Angew Chem Int Ed Engl. 19:1980;929-930.
    • (1980) Angew Chem Int Ed Engl , vol.19 , pp. 929-930
    • Juliá, S.1    Masana, J.2    Vega, J.C.3
  • 15
    • 0030998044 scopus 로고    scopus 로고
    • Preparation of polyamino acid catalysts for use in Juliá asymmetric epoxidation
    • Bentley P.A., Kroutil W., Littlechild J.A., Roberts S.M. Preparation of polyamino acid catalysts for use in Juliá asymmetric epoxidation. Chirality. 9:1997;198-202.
    • (1997) Chirality , vol.9 , pp. 198-202
    • Bentley, P.A.1    Kroutil, W.2    Littlechild, J.A.3    Roberts, S.M.4
  • 16
    • 0035969617 scopus 로고    scopus 로고
    • Highly enantioselective enone epoxidation catalyzed by short solid phase-bound peptides: Dominant role of peptide helicity
    • This article defines the minimal structural requirement for activity and enantioselectivity in the Juliá-Colonna epoxidation. Based on experimentation and calculations, a mechanistic proposal was put forward: catalysis and selectivity result from the binding of both the enone and hydroperoxide to the N-terminus of a helical peptide stretch
    • Berkessel A., Gasch N., Glaubitz K., Koch C. Highly enantioselective enone epoxidation catalyzed by short solid phase-bound peptides: dominant role of peptide helicity. Org Lett. 3:2001;3839-3842 This article defines the minimal structural requirement for activity and enantioselectivity in the Juliá-Colonna epoxidation. Based on experimentation and calculations, a mechanistic proposal was put forward: catalysis and selectivity result from the binding of both the enone and hydroperoxide to the N-terminus of a helical peptide stretch.
    • (2001) Org Lett , vol.3 , pp. 3839-3842
    • Berkessel, A.1    Gasch, N.2    Glaubitz, K.3    Koch, C.4
  • 17
    • 0037000505 scopus 로고    scopus 로고
    • Asymmetric epoxidation of α,β-unsaturated ketones catalyzed by poly(amino acids)
    • Lauret C., Roberts S.M. Asymmetric epoxidation of α,β-unsaturated ketones catalyzed by poly(amino acids). Aldrichimica Acta. 35:2002;47-51.
    • (2002) Aldrichimica Acta , vol.35 , pp. 47-51
    • Lauret, C.1    Roberts, S.M.2
  • 18
    • 0017998510 scopus 로고
    • 4-Dialkylaminopyridines as highly active acylation catalysts
    • Höfle G., Steglich W., Vorbrüggen H. 4-Dialkylaminopyridines as highly active acylation catalysts. Angew Chem Int Ed Engl. 17:1978;569-583.
    • (1978) Angew Chem Int Ed Engl , vol.17 , pp. 569-583
    • Höfle, G.1    Steglich, W.2    Vorbrüggen, H.3
  • 19
    • 0034354748 scopus 로고    scopus 로고
    • Asymmetric catalysis of acyl transfer by Lewis acids and nucleophiles. A review
    • Spivey A.C., Maddaford A. Asymmetric catalysis of acyl transfer by Lewis acids and nucleophiles. A review. Org Prep Proc Int. 32:2000;331-365.
    • (2000) Org Prep Proc Int , vol.32 , pp. 331-365
    • Spivey, A.C.1    Maddaford, A.2
  • 20
    • 0032564916 scopus 로고    scopus 로고
    • Kinetic resolution of alcohols catalyzed by tripeptides containing the N-alkylimidazole substructure
    • Miller S.J., Copeland G.T., Papaioannou N., Horstmann T.E., Ruel E.M. Kinetic resolution of alcohols catalyzed by tripeptides containing the N-alkylimidazole substructure. J Am Chem Soc. 120:1998;1629-1630.
    • (1998) J Am Chem Soc , vol.120 , pp. 1629-1630
    • Miller, S.J.1    Copeland, G.T.2    Papaioannou, N.3    Horstmann, T.E.4    Ruel, E.M.5
  • 21
    • 0000089981 scopus 로고    scopus 로고
    • Minimal acylase-like peptides. Conformational control of absolute stereospecificity
    • Copeland G.T., Jarvo E.R., Miller S.J. Minimal acylase-like peptides. Conformational control of absolute stereospecificity. J Org Chem. 63:1998;6784-6785.
    • (1998) J Org Chem , vol.63 , pp. 6784-6785
    • Copeland, G.T.1    Jarvo, E.R.2    Miller, S.J.3
  • 22
    • 0001625628 scopus 로고    scopus 로고
    • A His-Pro-Aib peptide that exhibits an Asx-Pro-turn-like structure
    • Blank J.T., Guerin D.J., Miller S.J. A His-Pro-Aib peptide that exhibits an Asx-Pro-turn-like structure. Org Lett. 2:2000;1247-1249.
    • (2000) Org Lett , vol.2 , pp. 1247-1249
    • Blank, J.T.1    Guerin, D.J.2    Miller, S.J.3
  • 24
    • 0036603597 scopus 로고    scopus 로고
    • Proton-activated fluorescence as a tool for simultaneous screening of combinatorial chemical reactions
    • •]). This presents an overview
    • •]). This presents an overview.
    • (2002) Curr Opin Chem Biol , vol.6 , pp. 333-338
    • Evans, C.A.1    Miller, S.J.2
  • 25
    • 0035838880 scopus 로고    scopus 로고
    • Fluorescence-based screening of asymmetric acylation catalysts through parallel enantiomer analysis. Identification of a catalyst for tertiary alcohol resolution
    • Jarvo E.R., Evans C.A., Copeland G.T., Miller S.J. Fluorescence-based screening of asymmetric acylation catalysts through parallel enantiomer analysis. Identification of a catalyst for tertiary alcohol resolution. J Org Chem. 66:2001;5522-5527.
    • (2001) J Org Chem , vol.66 , pp. 5522-5527
    • Jarvo, E.R.1    Evans, C.A.2    Copeland, G.T.3    Miller, S.J.4
  • 26
    • 0034807976 scopus 로고    scopus 로고
    • Selection of enantioselective acyl transfer catalysts from a pooled peptide library through a fluorescence-based activity assay: An approach to kinetic resolution of secondary alcohols of broad structural scope
    • 6 peptide library, using the 'sensor-on-the-bead' approach, affords catalysts for the enantioselective acylation of non-hydrogen bonding secondary alcohols
    • 6 peptide library, using the 'sensor-on-the-bead' approach, affords catalysts for the enantioselective acylation of non-hydrogen bonding secondary alcohols.
    • (2001) J Am Chem Soc , vol.123 , pp. 6496-6502
    • Copeland, G.T.1    Miller, S.J.2
  • 27
    • 0033526393 scopus 로고    scopus 로고
    • A chemosensor-based approach to catalyst discovery in solution and on solid support
    • Copeland G.T., Miller S.J. A chemosensor-based approach to catalyst discovery in solution and on solid support. J Am Chem Soc. 121:1999;4306-4307.
    • (1999) J Am Chem Soc , vol.121 , pp. 4306-4307
    • Copeland, G.T.1    Miller, S.J.2
  • 28
    • 0035904415 scopus 로고    scopus 로고
    • Discovery of a catalytic asymmetric phosphorylation through selection of a minimal kinase mimic: A concise total synthesis of D-myo-inositol-1-phosphate
    • ••]
    • ••].
    • (2001) J Am Chem Soc , vol.123 , pp. 10125-10126
    • Sculimbrene, B.R.1    Miller, S.J.2
  • 29
    • 0037010024 scopus 로고    scopus 로고
    • Enantio-divergence in small-molecule catalysis of asymmetric phosphorylation: Concise total synthesis of the enantiomeric D-myo-inositol-1-phosphate and D-myo-inositol-3-phosphate
    • The above two articles demonstrate the combinatorial approach by which peptide catalysts for the enantioselective phosphorylation of myo-inositol were found. This is the first example of a small-peptide kinase mimetic
    • Sculimbrene B.R., Morgan A.J., Miller S.J. Enantio-divergence in small-molecule catalysis of asymmetric phosphorylation: concise total synthesis of the enantiomeric D-myo-inositol-1-phosphate and D-myo-inositol-3-phosphate. J Am Chem Soc. 124:2002;11653-11656 The above two articles demonstrate the combinatorial approach by which peptide catalysts for the enantioselective phosphorylation of myo-inositol were found. This is the first example of a small-peptide kinase mimetic.
    • (2002) J Am Chem Soc , vol.124 , pp. 11653-11656
    • Sculimbrene, B.R.1    Morgan, A.J.2    Miller, S.J.3
  • 30
    • 0034675660 scopus 로고    scopus 로고
    • Asymmetric conjugate addition of azide to α,β-unsaturated carbonyl compounds catalyzed by simple peptides
    • Horstmann T.E., Guerin D.J., Miller S.J. Asymmetric conjugate addition of azide to α,β-unsaturated carbonyl compounds catalyzed by simple peptides. Angew Chem Int Ed Engl. 39:2000;3635-3638.
    • (2000) Angew Chem Int Ed Engl , vol.39 , pp. 3635-3638
    • Horstmann, T.E.1    Guerin, D.J.2    Miller, S.J.3
  • 31
    • 0037070622 scopus 로고    scopus 로고
    • Asymmetric azidation-cycloaddition with open-chain peptide-based catalysts. A sequential enantioselective route to triazoles
    • Guerin D.J., Miller S.J. Asymmetric azidation-cycloaddition with open-chain peptide-based catalysts. A sequential enantioselective route to triazoles. J Am Chem Soc. 124:2002;2134-2136.
    • (2002) J Am Chem Soc , vol.124 , pp. 2134-2136
    • Guerin, D.J.1    Miller, S.J.2
  • 32
    • 0035793657 scopus 로고    scopus 로고
    • Recent developments in catalytic asymmetric Strecker-type reactions
    • Yet L. Recent developments in catalytic asymmetric Strecker-type reactions. Angew Chem Int Ed Engl. 40:2001;875-877.
    • (2001) Angew Chem Int Ed Engl , vol.40 , pp. 875-877
    • Yet, L.1
  • 33
    • 0003554758 scopus 로고    scopus 로고
    • Schiff base catalysts for the asymmetric Strecker reaction indentified and optimized from parallel synthetic libraries
    • Sigman M.S., Jacobsen E.N. Schiff base catalysts for the asymmetric Strecker reaction indentified and optimized from parallel synthetic libraries. J Am Chem Soc. 120:1998;4901-4902.
    • (1998) J Am Chem Soc , vol.120 , pp. 4901-4902
    • Sigman, M.S.1    Jacobsen, E.N.2
  • 34
    • 0034599654 scopus 로고    scopus 로고
    • A general catalyst for the asymmetric Strecker reaction
    • Sigman M.S., Vachal P., Jacobsen E.N. A general catalyst for the asymmetric Strecker reaction. Angew Chem Int Ed Engl. 39:2000;1279-1281.
    • (2000) Angew Chem Int Ed Engl , vol.39 , pp. 1279-1281
    • Sigman, M.S.1    Vachal, P.2    Jacobsen, E.N.3
  • 35
    • 0034704642 scopus 로고    scopus 로고
    • Enantioselective catalytic addition of HCN to ketoimines. Catalytic synthesis of quarternary amino acids
    • Vachal P., Jacobsen E.N. Enantioselective catalytic addition of HCN to ketoimines. Catalytic synthesis of quarternary amino acids. Org Lett. 2:2000;867-870.
    • (2000) Org Lett , vol.2 , pp. 867-870
    • Vachal, P.1    Jacobsen, E.N.2
  • 36
    • 0037189898 scopus 로고    scopus 로고
    • Structure-based analysis and optimization of a highly enantioselective catalyst for the Strecker reaction
    • This article decribes the development of the most selective and broadly applicable catalyst available to date for the asymmetric addition of HCN to imines (i.e. the asymmetric Strecker reaction)
    • Vachal P., Jacobsen E.N. Structure-based analysis and optimization of a highly enantioselective catalyst for the Strecker reaction. J Am Chem Soc. 124:2002;10012-10014 This article decribes the development of the most selective and broadly applicable catalyst available to date for the asymmetric addition of HCN to imines (i.e. the asymmetric Strecker reaction).
    • (2002) J Am Chem Soc , vol.124 , pp. 10012-10014
    • Vachal, P.1    Jacobsen, E.N.2
  • 37
    • 0034599407 scopus 로고    scopus 로고
    • IR-thermographic screening of thermoneutral or endothermic transformations: The ring-closing olefin metathesis reaction
    • Reetz M.T., Becker M.H., Liebl M., Fürstner A. IR-thermographic screening of thermoneutral or endothermic transformations: the ring-closing olefin metathesis reaction. Angew Chem Int Ed Engl. 39:2000;1236-1239.
    • (2000) Angew Chem Int Ed Engl , vol.39 , pp. 1236-1239
    • Reetz, M.T.1    Becker, M.H.2    Liebl, M.3    Fürstner, A.4
  • 38
    • 0035001299 scopus 로고    scopus 로고
    • Infrared-thermographic screening of the activity and enantioselectivity of enzymes
    • Reetz M.T., Hermes M., Becker M.H. Infrared-thermographic screening of the activity and enantioselectivity of enzymes. Appl Microbiol Biotech. 55:2001;531-536.
    • (2001) Appl Microbiol Biotech , vol.55 , pp. 531-536
    • Reetz, M.T.1    Hermes, M.2    Becker, M.H.3
  • 39
    • 0037858846 scopus 로고    scopus 로고
    • Discovery of novel homogeneous lanthanide catalysts by IR-thermography: Epoxide opening with alcohols and Baeyer-Villiger oxidations with hydrogen peroxide
    • in press
    • Berkessel A, Ashkenazi E, Andreae MRM: Discovery of novel homogeneous lanthanide catalysts by IR-thermography: epoxide opening with alcohols and Baeyer-Villiger oxidations with hydrogen peroxide. Appl Catal A General 2003, in press.
    • (2003) Appl Catal A General
    • Berkessel, A.1    Ashkenazi, E.2    Andreae, M.R.M.3
  • 40
    • 0037090667 scopus 로고    scopus 로고
    • New methods for the high-throughput screening of enantioselective catalysts and biocatalysts
    • Reetz M.T. New methods for the high-throughput screening of enantioselective catalysts and biocatalysts. Angew Chem Int Ed Engl. 41:2002;1335-1338.
    • (2002) Angew Chem Int Ed Engl , vol.41 , pp. 1335-1338
    • Reetz, M.T.1
  • 41
    • 0035801625 scopus 로고    scopus 로고
    • Color indicators of molecular chirality based on doped liquid crystals
    • Van Delden R.A., Feringa B.L. Color indicators of molecular chirality based on doped liquid crystals. Angew Chem Int Ed Engl. 40:2001;3198-3200.
    • (2001) Angew Chem Int Ed Engl , vol.40 , pp. 3198-3200
    • Van Delden, R.A.1    Feringa, B.L.2
  • 42
    • 0035900973 scopus 로고    scopus 로고
    • Reaction microarrays: A method for rapidly determining the enantiomeric excess of thousands of samples
    • Korbel G.A., Lalic G., Shair M.D. Reaction microarrays: a method for rapidly determining the enantiomeric excess of thousands of samples. J Am Chem Soc. 123:2001;361-362.
    • (2001) J Am Chem Soc , vol.123 , pp. 361-362
    • Korbel, G.A.1    Lalic, G.2    Shair, M.D.3
  • 43
    • 0034669263 scopus 로고    scopus 로고
    • A polymeric and fluorescent gel for combinatorial screening of catalysts
    • This article describes the use of gels for the immobilization of bead-bound libraries. As a result, site-selective detection of acylase activity becomes possible by a fluorescence probe present in the gel, and not on the individual beads
    • Harris R.F., Nation A.J., Copeland G.T., Miller S.J. A polymeric and fluorescent gel for combinatorial screening of catalysts. J Am Chem Soc. 122:2000;11270-11271 This article describes the use of gels for the immobilization of bead-bound libraries. As a result, site-selective detection of acylase activity becomes possible by a fluorescence probe present in the gel, and not on the individual beads.
    • (2000) J Am Chem Soc , vol.122 , pp. 11270-11271
    • Harris, R.F.1    Nation, A.J.2    Copeland, G.T.3    Miller, S.J.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.