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Volumn 21, Issue 1, 2009, Pages 145-151

Chirality sensing with pores: Reactive signal amplifiers for otherwise undetectable small molecules

Author keywords

Chirality; Enantiomeric excess; Enzymes; Fluorescence; Ion channels; Pores; Stereoselectivity

Indexed keywords

HYDRAZIDE; LACTATE 2 MONOOXYGENASE; LACTIC ACID;

EID: 60849136034     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20597     Document Type: Article
Times cited : (3)

References (48)
  • 2
    • 39749134224 scopus 로고    scopus 로고
    • Chirality sensing with synthetic pores
    • Tanaka H, Matile S. Chirality sensing with synthetic pores. Chirality 2008;20:307-312.
    • (2008) Chirality , vol.20 , pp. 307-312
    • Tanaka, H.1    Matile, S.2
  • 4
    • 0026075430 scopus 로고
    • Cascade blue derivatives: Water soluble, reactive, blue emission dyes evaluated as fluorescent labels and tracers
    • Whitaker JE, Haugland RP, Moore PL, Hewitt PC, Reese M, Haugland RP. Cascade blue derivatives: water soluble, reactive, blue emission dyes evaluated as fluorescent labels and tracers. Anal Biochem 1991;198:119-130.
    • (1991) Anal Biochem , vol.198 , pp. 119-130
    • Whitaker, J.E.1    Haugland, R.P.2    Moore, P.L.3    Hewitt, P.C.4    Reese, M.5    Haugland, R.P.6
  • 5
    • 0036856444 scopus 로고    scopus 로고
    • Rigid-rod β-barrels with internal cascade blue cofactors - catalysis of amide, carbonate and ester hydrolysis
    • Som A, Matile S. Rigid-rod β-barrels with internal cascade blue cofactors - catalysis of amide, carbonate and ester hydrolysis. Eur J Org Chem 2002:3874-3883.
    • (2002) Eur J Org Chem , pp. 3874-3883
    • Som, A.1    Matile, S.2
  • 6
    • 0035961023 scopus 로고    scopus 로고
    • p-Octiphenyl β-barrels with ion channel and esterase activily
    • Baumeister B, Sakai N, Matile S. p-Octiphenyl β-barrels with ion channel and esterase activily. Org Lett 2001;3:4229-4232.
    • (2001) Org Lett , vol.3 , pp. 4229-4232
    • Baumeister, B.1    Sakai, N.2    Matile, S.3
  • 7
    • 34248359507 scopus 로고    scopus 로고
    • Analyte sensing across membranes with artificial pores
    • Matile S, Tanaka H, Litvinchuk S. Analyte sensing across membranes with artificial pores. Top Curr Chem 2007;277:219-250.
    • (2007) Top Curr Chem , vol.277 , pp. 219-250
    • Matile, S.1    Tanaka, H.2    Litvinchuk, S.3
  • 8
    • 34247542512 scopus 로고    scopus 로고
    • Fluorescent ADP sensing in physiological conditions based on cooperative inhibition of a miniature esterase
    • Vial L, Dumy P. Fluorescent ADP sensing in physiological conditions based on cooperative inhibition of a miniature esterase. J Am Chem Soc 2007;129:4884-4885.
    • (2007) J Am Chem Soc , vol.129 , pp. 4884-4885
    • Vial, L.1    Dumy, P.2
  • 10
    • 33745852649 scopus 로고    scopus 로고
    • Controlled release of volatile aldehydes and ketones by reversible hydrazone formation -classical profragances are getting dynamic
    • Levrand B, Ruff Y, Lehn JM, Herrmann A. Controlled release of volatile aldehydes and ketones by reversible hydrazone formation -classical profragances are getting dynamic. Chem Commun 2006;41:2965-2967.
    • (2006) Chem Commun , vol.41 , pp. 2965-2967
    • Levrand, B.1    Ruff, Y.2    Lehn, J.M.3    Herrmann, A.4
  • 11
    • 33644946430 scopus 로고    scopus 로고
    • One-pot and sequential organic chemistry on an enzyme surface to tether a fluorescent probe at the proximity of the active site with restoring enzyme activity
    • Takaoka Y, Tsutsumi H, Kasagi N, Nakata E, Hamachi I. One-pot and sequential organic chemistry on an enzyme surface to tether a fluorescent probe at the proximity of the active site with restoring enzyme activity. J Am Chem Soc 2006;128:3273-3280.
    • (2006) J Am Chem Soc , vol.128 , pp. 3273-3280
    • Takaoka, Y.1    Tsutsumi, H.2    Kasagi, N.3    Nakata, E.4    Hamachi, I.5
  • 12
    • 0028960723 scopus 로고
    • Unprotected peptides as building blocks for the synthesis of peptide dendrimers with oxime, hydrazone, and thiazolidine linkages
    • Shao J, Tam JP. Unprotected peptides as building blocks for the synthesis of peptide dendrimers with oxime, hydrazone, and thiazolidine linkages. J Am Chem Soc 1995;117:3893-3899.
    • (1995) J Am Chem Soc , vol.117 , pp. 3893-3899
    • Shao, J.1    Tam, J.P.2
  • 14
    • 42649101335 scopus 로고    scopus 로고
    • Boronic acid converters for reactive hydrazide amplifiers: Polyphenol sensing in green tea with synthetic pores
    • Hagihara S, Tanaka H, Matile S. Boronic acid converters for reactive hydrazide amplifiers: polyphenol sensing in green tea with synthetic pores. J Am Chem Soc 2008;130:5656-5657.
    • (2008) J Am Chem Soc , vol.130 , pp. 5656-5657
    • Hagihara, S.1    Tanaka, H.2    Matile, S.3
  • 15
    • 41549147781 scopus 로고    scopus 로고
    • Screening of π-basic naphthalene and anthracene amplifiers for π-acidic synthetic pore sensors
    • Hagihara S, Gremaud L, Bollot G, Mareda J, Matile S. Screening of π-basic naphthalene and anthracene amplifiers for π-acidic synthetic pore sensors. J Am Chem Soc 2008;130:4347-4351.
    • (2008) J Am Chem Soc , vol.130 , pp. 4347-4351
    • Hagihara, S.1    Gremaud, L.2    Bollot, G.3    Mareda, J.4    Matile, S.5
  • 18
    • 33749164306 scopus 로고    scopus 로고
    • A cost-effective method for the optical transduction of chemical reactions. Application to hyaluronidase inhibitor screening with polyarginine-counteranion complexes in lipid bilayers
    • Miyatake T, Nishihara M, Matile S. A cost-effective method for the optical transduction of chemical reactions. Application to hyaluronidase inhibitor screening with polyarginine-counteranion complexes in lipid bilayers. J Am Chem Soc 2006;128:12420-12421.
    • (2006) J Am Chem Soc , vol.128 , pp. 12420-12421
    • Miyatake, T.1    Nishihara, M.2    Matile, S.3
  • 19
    • 60149083245 scopus 로고    scopus 로고
    • Detection of the activity of ion channels and pores with circular dichroism spectroscopy: G-quartets as functional CD probes within chirogenic vesicles
    • in press, DOI: 10.1002/ chir.20526
    • Hennig A, Matile S. Detection of the activity of ion channels and pores with circular dichroism spectroscopy: G-quartets as functional CD probes within chirogenic vesicles. Chirality (in press); DOI: 10.1002/ chir.20526.
    • Chirality
    • Hennig, A.1    Matile, S.2
  • 20
    • 33846666853 scopus 로고    scopus 로고
    • Synthetic ion channels in bilayer membranes
    • Fyles TM. Synthetic ion channels in bilayer membranes. Chem Soc Rev 2007;36:335-347.
    • (2007) Chem Soc Rev , vol.36 , pp. 335-347
    • Fyles, T.M.1
  • 21
    • 33846667747 scopus 로고    scopus 로고
    • Development of synthetic membrane transporters for anions
    • Davis AP, Sheppard DN, Smith BD. Development of synthetic membrane transporters for anions. Chem Soc Rev 2007;36:348-357.
    • (2007) Chem Soc Rev , vol.36 , pp. 348-357
    • Davis, A.P.1    Sheppard, D.N.2    Smith, B.D.3
  • 22
    • 33846691530 scopus 로고    scopus 로고
    • Supramolecular architectures generated by self-assembly of guanosine derivatives
    • Davis JT, Spada GP. Supramolecular architectures generated by self-assembly of guanosine derivatives. Chem Soc Rev 2007;36:296-313.
    • (2007) Chem Soc Rev , vol.36 , pp. 296-313
    • Davis, J.T.1    Spada, G.P.2
  • 24
    • 34247628531 scopus 로고    scopus 로고
    • Synthesis, characterization and cytolytic activity of alpha-helical amphiphilic peptide nanostructures containing crown ethers
    • Boudreault PL, Voyer N. Synthesis, characterization and cytolytic activity of alpha-helical amphiphilic peptide nanostructures containing crown ethers. Org Biomol Chem 2007:5;1459-1465.
    • (2007) Org Biomol Chem , vol.5 , pp. 1459-1465
    • Boudreault, P.L.1    Voyer, N.2
  • 26
    • 12744254226 scopus 로고    scopus 로고
    • Signal-triggered transmembrane ion transport through synthetic channels
    • Hector RS, Gin MS. Signal-triggered transmembrane ion transport through synthetic channels. Supramol Chem 2005;17:129-134.
    • (2005) Supramol Chem , vol.17 , pp. 129-134
    • Hector, R.S.1    Gin, M.S.2
  • 28
    • 4143143476 scopus 로고    scopus 로고
    • Recent synthetic ion channels and pores
    • Matile S, Som A, Sordé N. Recent synthetic ion channels and pores. Tetrahedron 2004;60:6405-6435.
    • (2004) Tetrahedron , vol.60 , pp. 6405-6435
    • Matile, S.1    Som, A.2    Sordé, N.3
  • 29
    • 57249098817 scopus 로고    scopus 로고
    • Synthetic models of cation-conducting channels
    • Gokel GW, Mukhopadhyay A. Synthetic models of cation-conducting channels. Chem Soc Rev 2001:30;274-286.
    • (2001) Chem Soc Rev , vol.30 , pp. 274-286
    • Gokel, G.W.1    Mukhopadhyay, A.2
  • 30
    • 0032705164 scopus 로고    scopus 로고
    • Model membranes: Developments in functional micelles and vesicles
    • Scrimin P, Tecilla P. Model membranes: developments in functional micelles and vesicles. Curr Opin Chem Biol 1999;3:730-735.
    • (1999) Curr Opin Chem Biol , vol.3 , pp. 730-735
    • Scrimin, P.1    Tecilla, P.2
  • 31
    • 0000843454 scopus 로고
    • Artificial non-peptide single ion channels
    • Kobuke Y, Ueda K, Sokabe M. Artificial non-peptide single ion channels. J Am Chem Soc 1992;114:7618-7622.
    • (1992) J Am Chem Soc , vol.114 , pp. 7618-7622
    • Kobuke, Y.1    Ueda, K.2    Sokabe, M.3
  • 32
    • 33744844198 scopus 로고
    • A macrocyclic tetraether bolaamphiphile and an oligoaminodicarboxylate combine to form monolayered, porous vesicle membranes, which are reversibly sealed by EDTA and other bulky anions
    • Fuhrhop JH, Liman U, Koesling V. A macrocyclic tetraether bolaamphiphile and an oligoaminodicarboxylate combine to form monolayered, porous vesicle membranes, which are reversibly sealed by EDTA and other bulky anions. J Am Chem Soc 1988;110:6840-6845.
    • (1988) J Am Chem Soc , vol.110 , pp. 6840-6845
    • Fuhrhop, J.H.1    Liman, U.2    Koesling, V.3
  • 33
    • 0000951266 scopus 로고
    • F-Tetrasubstituted β-cyclodextrin as artificial channel compound
    • Tabushi I, Kuroda Y, Yokota K. A,B,D,F-Tetrasubstituted β-cyclodextrin as artificial channel compound. Tetrahedron Lett 1982;23:4601-4604.
    • (1982) Tetrahedron Lett , vol.23 , pp. 4601-4604
    • Tabushi, I.1    Kuroda, Y.2    Yokota, K.A.B.D.3
  • 34
    • 13844306732 scopus 로고    scopus 로고
    • Rigid-rod molecules in biomembrane models: From hydrogen-bonded chains to synthetic multifunctional pores
    • Sakai N, Mareda J, Matile S. Rigid-rod molecules in biomembrane models: from hydrogen-bonded chains to synthetic multifunctional pores. Arc Chem Res 2005;38:79-87.
    • (2005) Arc Chem Res , vol.38 , pp. 79-87
    • Sakai, N.1    Mareda, J.2    Matile, S.3
  • 35
    • 21644458175 scopus 로고    scopus 로고
    • Sugar sensing with synthetic multifunctional pores
    • Litvinchuk S, Sordé N, Matile S. Sugar sensing with synthetic multifunctional pores. J Am Chem Soc 2005;127:9316-9317.
    • (2005) J Am Chem Soc , vol.127 , pp. 9316-9317
    • Litvinchuk, S.1    Sordé, N.2    Matile, S.3
  • 36
    • 4043107662 scopus 로고    scopus 로고
    • Thermodynamic and kinetic stability of synthetic multifunctional rigid-rod β-barrel pores: Evidence for supra-molecular catalysis
    • Litvinchuk S, Ballot G, Mareda J, Som A, Ronan D, Shah MR, Perrottet P, Sakai N, Matile S. Thermodynamic and kinetic stability of synthetic multifunctional rigid-rod β-barrel pores: evidence for supra-molecular catalysis. J Am Chem Soc 2004;126:10067-10075.
    • (2004) J Am Chem Soc , vol.126 , pp. 10067-10075
    • Litvinchuk, S.1    Ballot, G.2    Mareda, J.3    Som, A.4    Ronan, D.5    Shah, M.R.6    Perrottet, P.7    Sakai, N.8    Matile, S.9
  • 37
    • 0037159683 scopus 로고    scopus 로고
    • Fluorometric detection of enzyme activity with synthetic supramolecular pores
    • Das G, Talukdar P, Matile S. Fluorometric detection of enzyme activity with synthetic supramolecular pores. Science 2002;298:1600-1602.
    • (2002) Science , vol.298 , pp. 1600-1602
    • Das, G.1    Talukdar, P.2    Matile, S.3
  • 38
    • 0142059862 scopus 로고    scopus 로고
    • Enzyme screening with synthetic multifunctional pores: Focus on biopolymers
    • Sordé N, Das G, Matile S. Enzyme screening with synthetic multifunctional pores: focus on biopolymers. Proc Natl Acad Sci USA 2003;100:11964-11969.
    • (2003) Proc Natl Acad Sci USA , vol.100 , pp. 11964-11969
    • Sordé, N.1    Das, G.2    Matile, S.3
  • 39
    • 33645694226 scopus 로고    scopus 로고
    • Substrate-independent transduction of chromophore-free organic and biomolecular transformations into color
    • Das G, Matile S. Substrate-independent transduction of chromophore-free organic and biomolecular transformations into color. Chem Eur J 2006:12;2936-2944.
    • (2006) Chem Eur J , vol.12 , pp. 2936-2944
    • Das, G.1    Matile, S.2
  • 40
    • 0036084211 scopus 로고    scopus 로고
    • Emerging methods for the rapid determination of enantiomeric excess
    • Finn MG. Emerging methods for the rapid determination of enantiomeric excess. Chirality 2002;14:534-540.
    • (2002) Chirality , vol.14 , pp. 534-540
    • Finn, M.G.1
  • 41
    • 3543116602 scopus 로고    scopus 로고
    • Enzyme assays for high-throughput screening
    • Goddard JP, Reymond JL. Enzyme assays for high-throughput screening. Curr Opin Biotechnol 2004;15:314-322.
    • (2004) Curr Opin Biotechnol , vol.15 , pp. 314-322
    • Goddard, J.P.1    Reymond, J.L.2
  • 42
    • 20944445400 scopus 로고    scopus 로고
    • Double-cuvette ISES: In situ estimation of enantioselectivity and relative rate for catalyst screening
    • Dey S, Karukurichi KR, Shen W, Berkowitz DB. Double-cuvette ISES: in situ estimation of enantioselectivity and relative rate for catalyst screening. J Am Chem Soc. 2005;127:8610-8611.
    • (2005) J Am Chem Soc , vol.127 , pp. 8610-8611
    • Dey, S.1    Karukurichi, K.R.2    Shen, W.3    Berkowitz, D.B.4
  • 43
    • 27644453538 scopus 로고    scopus 로고
    • Using enzyme inhibition as a high throughput method to measure the enantiomeric excess of a chiral sulfoxide
    • Sprout CM, Seto CT. Using enzyme inhibition as a high throughput method to measure the enantiomeric excess of a chiral sulfoxide. Org Lett 2005;7:5099-5102.
    • (2005) Org Lett , vol.7 , pp. 5099-5102
    • Sprout, C.M.1    Seto, C.T.2
  • 44
    • 4544276645 scopus 로고    scopus 로고
    • High-throughput measurement of the enantiomeric excess of chiral alcohols by using two enzymes
    • Li Z, Butikofer L, Witholt B. High-throughput measurement of the enantiomeric excess of chiral alcohols by using two enzymes. Angew Chem Int Ed 2004;43:1698-1702.
    • (2004) Angew Chem Int Ed , vol.43 , pp. 1698-1702
    • Li, Z.1    Butikofer, L.2    Witholt, B.3
  • 45
    • 0035913739 scopus 로고    scopus 로고
    • Abato P, Seto CT. EMDee: an enzymatic method for determining enantiomeric excess. J Am Chem Soc 2001;123:9206-9207.
    • Abato P, Seto CT. EMDee: an enzymatic method for determining enantiomeric excess. J Am Chem Soc 2001;123:9206-9207.
  • 47
    • 0019619260 scopus 로고
    • Inactivation of L-lactate monooxygenase by nitration with tetranitromethane
    • Durfor CN, Cromartie TH. Inactivation of L-lactate monooxygenase by nitration with tetranitromethane. Arch. Biochem Biophys 1981; 210:710-716.
    • (1981) Arch. Biochem Biophys , vol.210 , pp. 710-716
    • Durfor, C.N.1    Cromartie, T.H.2


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