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Volumn 41, Issue 5, 2011, Pages 399-412

The Relative Rates of Thiol-Thioester Exchange and Hydrolysis for Alkyl and Aryl Thioalkanoates in Water

Author keywords

Dynamic covalent chemistry; Hydrolysis; Origin of life; Prebiotic chemistry; Thioesters; Thiol thioester exchange

Indexed keywords

ACETIC ACID DERIVATIVE; ALKANESULFONIC ACID; ARYLSULFONIC ACID DERIVATIVE; METHYL THIOACETATE; SULFIDE; THIOL DERIVATIVE; WATER;

EID: 80052967444     PISSN: 01696149     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11084-011-9243-4     Document Type: Article
Times cited : (134)

References (36)
  • 1
    • 0039441836 scopus 로고
    • The rates of hydrolysis of two thiol esters in water
    • doi:10.1021/jo01261a070
    • Barnett R, Jencks WP (1969) The rates of hydrolysis of two thiol esters in water. J Org Chem 34: 2777-2779. doi: 10. 1021/jo01261a070.
    • (1969) J Org Chem , vol.34 , pp. 2777-2779
    • Barnett, R.1    Jencks, W.P.2
  • 4
    • 0000643086 scopus 로고    scopus 로고
    • Kinetics and mechanisms of reactions of thiol, thiono, and dithio analogues of carboxylic esters with nucleophiles
    • doi:10.1021/cr990001d
    • Castro EA (1999) Kinetics and mechanisms of reactions of thiol, thiono, and dithio analogues of carboxylic esters with nucleophiles. Chem Rev 99: 3505-3524. doi: 10. 1021/cr990001d.
    • (1999) Chem Rev , vol.99 , pp. 3505-3524
    • Castro, E.A.1
  • 5
    • 34547175876 scopus 로고    scopus 로고
    • Kinetics and mechanisms of reactions of thiol, thiono, and dithio analogues of carboxylic esters with nucleophiles. An update
    • doi:10.1080/17415990701415718
    • Castro EA (2007) Kinetics and mechanisms of reactions of thiol, thiono, and dithio analogues of carboxylic esters with nucleophiles. An update. J Sulfur Chem 28: 401-429. doi: 10. 1080/17415990701415718.
    • (2007) J Sulfur Chem , vol.28 , pp. 401-429
    • Castro, E.A.1
  • 6
    • 37749048615 scopus 로고    scopus 로고
    • Committee on the Limits of Organic Life in Planetary Systems, Committee on the Origins and Evolution of Life, The National Research Council, Washington: The National Academies
    • Committee on the Limits of Organic Life in Planetary Systems, Committee on the Origins and Evolution of Life, The National Research Council (2007) The limits of organic life in planetary systems. The National Academies, Washington.
    • (2007) The Limits of Organic Life in Planetary Systems
  • 8
    • 0000195317 scopus 로고
    • The relative nucleophilic character of several mercaptans toward ethylene oxide
    • doi:10.1021/ja01495a028
    • Danehy JP, Noel CJ (1960) The relative nucleophilic character of several mercaptans toward ethylene oxide. J Am Chem Soc 82: 2511-2515. doi: 10. 1021/ja01495a028.
    • (1960) J Am Chem Soc , vol.82 , pp. 2511-2515
    • Danehy, J.P.1    Noel, C.J.2
  • 9
    • 0033791223 scopus 로고    scopus 로고
    • Synthesis of native proteins by chemical ligation
    • doi:10.1146/annurev.biochem.69.1.923
    • Dawson PE, Kent SBH (2000) Synthesis of native proteins by chemical ligation. Annu Rev Biochem 69: 923-960. doi: 10. 1146/annurev. biochem. 69. 1. 923.
    • (2000) Annu Rev Biochem , vol.69 , pp. 923-960
    • Dawson, P.E.1    Kent, S.B.H.2
  • 11
    • 0030973396 scopus 로고    scopus 로고
    • Modulation of reactivity in native chemical ligation through the use of thiol additives
    • doi:10.1021/ja962656r
    • Dawson PE, Churchill MJ, Ghadiri MR, Kent SBH (1997) Modulation of reactivity in native chemical ligation through the use of thiol additives. J Am Chem Soc 119: 4325-4329. doi: 10. 1021/ja962656r.
    • (1997) J Am Chem Soc , vol.119 , pp. 4325-4329
    • Dawson, P.E.1    Churchill, M.J.2    Ghadiri, M.R.3    Kent, S.B.H.4
  • 12
    • 0004247828 scopus 로고
    • Burlington: Neil Patterson Publishers
    • de Duve C (1991) Blueprint for a cell. Neil Patterson Publishers, Burlington.
    • (1991) Blueprint for a Cell
    • de Duve, C.1
  • 13
    • 33947489359 scopus 로고
    • Nucleophilic displacement reactions at the thiol ester bond. IV. General base catalyzed hydrolysis of ethyl trifluoroacetate. Kinetic evidence for the formation of a tetrahedral intermediate
    • doi:10.1021/ja01096a024
    • Fedor LR, Bruice TC (1965) Nucleophilic displacement reactions at the thiol ester bond. IV. General base catalyzed hydrolysis of ethyl trifluoroacetate. Kinetic evidence for the formation of a tetrahedral intermediate. J Am Chem Soc 87: 4138-4147. doi: 10. 1021/ja01096a024.
    • (1965) J Am Chem Soc , vol.87 , pp. 4138-4147
    • Fedor, L.R.1    Bruice, T.C.2
  • 14
    • 67049173798 scopus 로고    scopus 로고
    • Applying biological principles to the assembly and selection of synthetic superstructures
    • doi:10.1039/b104962n
    • Greig LM, Philp D (2001) Applying biological principles to the assembly and selection of synthetic superstructures. Chem Soc Rev 30: 287-302. doi: 10. 1039/b104962n.
    • (2001) Chem Soc Rev , vol.30 , pp. 287-302
    • Greig, L.M.1    Philp, D.2
  • 15
    • 33845933133 scopus 로고    scopus 로고
    • An antiparallel alpha-helical coiled-coil model system for rapid assessment of side-chain recognition at the hydrophobic interface
    • doi:10.1021/ja067178r
    • Hadley EB, Gellman SH (2006) An antiparallel alpha-helical coiled-coil model system for rapid assessment of side-chain recognition at the hydrophobic interface. J Am Chem Soc 128: 16444-16445. doi: 10. 1021/ja067178r.
    • (2006) J Am Chem Soc , vol.128 , pp. 16444-16445
    • Hadley, E.B.1    Gellman, S.H.2
  • 16
    • 0030620774 scopus 로고    scopus 로고
    • Activated acetic acid by carbon fixation on (Fe, Ni)S under primordial conditions
    • doi:10.1126/science.276.5310.245
    • Huber C, Wächtershäuser G (1997) Activated acetic acid by carbon fixation on (Fe, Ni)S under primordial conditions. Science 276: 245-247. doi: 10. 1126/science. 276. 5310. 245.
    • (1997) Science , vol.276 , pp. 245-247
    • Huber, C.1    Wächtershäuser, G.2
  • 17
    • 0032584573 scopus 로고    scopus 로고
    • Peptides by activation of amino acids with CO on (Ni, Fe)S surfaces: implications for the origin of life
    • doi:10.1126/science.281.5377.670
    • Huber C, Wächtershäuser G (1998) Peptides by activation of amino acids with CO on (Ni, Fe)S surfaces: implications for the origin of life. Science 281: 670-672. doi: 10. 1126/science. 281. 5377. 670.
    • (1998) Science , vol.281 , pp. 670-672
    • Huber, C.1    Wächtershäuser, G.2
  • 18
    • 33847088916 scopus 로고
    • Nonlinear structure-reactivity correlations. Acyl transfer between sulfur and oxygen nucleophiles
    • doi:10.1021/ja00444a023
    • Hupe DJ, Jencks WP (1977) Nonlinear structure-reactivity correlations. Acyl transfer between sulfur and oxygen nucleophiles. J Am Chem Soc 99: 451-464. doi: 10. 1021/ja00444a023.
    • (1977) J Am Chem Soc , vol.99 , pp. 451-464
    • Hupe, D.J.1    Jencks, W.P.2
  • 20
    • 0000025142 scopus 로고
    • Free energy of thiol ester hydrolysis
    • Jencks WP, Cordes S, Carriuolo J (1960) Free energy of thiol ester hydrolysis. J Biol Chem 235: 3608-3614.
    • (1960) J Biol Chem , vol.235 , pp. 3608-3614
    • Jencks, W.P.1    Cordes, S.2    Carriuolo, J.3
  • 22
    • 0001604272 scopus 로고
    • pH optimization of nucleophilic reactions in water
    • doi:10.1021/ja00034a040
    • King JF, Rathore R, Lam JYL, Guo ZR, Klassen DF (1992) pH optimization of nucleophilic reactions in water. J Am Chem Soc 114: 3028-3033. doi: 10. 1021/ja00034a040.
    • (1992) J Am Chem Soc , vol.114 , pp. 3028-3033
    • King, J.F.1    Rathore, R.2    Lam, J.Y.L.3    Guo, Z.R.4    Klassen, D.F.5
  • 23
    • 0028582374 scopus 로고
    • The early precambrian atmosphere and hydrosphere: thermodynamic constraints from mineral deposits
    • doi:10.2113/gsecongeo.89.7.1581
    • Krupp R, Oberthür T, Hirdes W (1994) The early precambrian atmosphere and hydrosphere: thermodynamic constraints from mineral deposits. Econ Geol 89: 1581-1598. doi: 10. 2113/gsecongeo. 89. 7. 1581.
    • (1994) Econ Geol , vol.89 , pp. 1581-1598
    • Krupp, R.1    Oberthür, T.2    Hirdes, W.3
  • 24
    • 4544244707 scopus 로고    scopus 로고
    • Catalytic self-screening of cholinesterase substrates from a dynamic combinatorial thioester library
    • doi:10.1002/anie.200454165
    • Larsson R, Pei ZC, Ramström O (2004) Catalytic self-screening of cholinesterase substrates from a dynamic combinatorial thioester library. Angew Chem Int Ed 43: 3716-3718. doi: 10. 1002/anie. 200454165.
    • (2004) Angew Chem Int Ed , vol.43 , pp. 3716-3718
    • Larsson, R.1    Pei, Z.C.2    Ramström, O.3
  • 25
    • 18044382132 scopus 로고    scopus 로고
    • Expanding diversity in dynamic combinatorial libraries: simultaneous exchange of disulfide and thioester linkages
    • doi: 10.1039/b500638d
    • Leclaire J, Vial L, Otto S, Sanders JKM (2005) Expanding diversity in dynamic combinatorial libraries: simultaneous exchange of disulfide and thioester linkages. Chem Commun: 1959-1961. doi: 10. 1039/b500638d.
    • (2005) Chem Commun: 1959-1961
    • Leclaire, J.1    Vial, L.2    Otto, S.3    Sanders, J.K.M.4
  • 26
    • 0028184159 scopus 로고
    • Hydrothermal and oceanic pH conditions of possible relevance to the origin of life
    • Macleod G, McKeown C, Hall AJ, Russell MJ (1994) Hydrothermal and oceanic pH conditions of possible relevance to the origin of life. Orig Life Evol Biosph 24: 19-41.
    • (1994) Orig Life Evol Biosph , vol.24 , pp. 19-41
    • Macleod, G.1    McKeown, C.2    Hall, A.J.3    Russell, M.J.4
  • 27
    • 0022577134 scopus 로고
    • A stereocontrolled synthesis of thienamycin from 6-aminopenicillanic acid
    • doi:10.1021/jo00353a025
    • Maruyama H, Hiraoka T (1986) A stereocontrolled synthesis of thienamycin from 6-aminopenicillanic acid. J Org Chem 51: 399-402. doi: 10. 1021/jo00353a025.
    • (1986) J Org Chem , vol.51 , pp. 399-402
    • Maruyama, H.1    Hiraoka, T.2
  • 28
    • 0343433408 scopus 로고    scopus 로고
    • Cysteine proteases and their inhibitors
    • doi:10.1021/cr950025u
    • Otto HH, Schirmeister T (1997) Cysteine proteases and their inhibitors. Chem Rev 97: 133-171. doi: 10. 1021/cr950025u.
    • (1997) Chem Rev , vol.97 , pp. 133-171
    • Otto, H.H.1    Schirmeister, T.2
  • 30
    • 67650407671 scopus 로고    scopus 로고
    • Dynamic polythioesters via ring-opening polymerization of 1,4-thiazine-2,5-diones
    • doi:10.1039/b903612a
    • Ura Y, Al-Sayah M, Montenegro J, Beierle JM, Leman LJ, Ghadiri MR (2009) Dynamic polythioesters via ring-opening polymerization of 1, 4-thiazine-2, 5-diones. Org Biomol Chem 7: 2878-2884. doi: 10. 1039/b903612a.
    • (2009) Org Biomol Chem , vol.7 , pp. 2878-2884
    • Ura, Y.1    Al-Sayah, M.2    Montenegro, J.3    Beierle, J.M.4    Leman, L.J.5    Ghadiri, M.R.6
  • 32
    • 0026444704 scopus 로고
    • Groundworks for an evolutionary biochemistry-the iron sulfur world
    • Wächtershäuser G (1992) Groundworks for an evolutionary biochemistry-the iron sulfur world. Prog Biophys Mol Biol 58: 85-201.
    • (1992) Prog Biophys Mol Biol , vol.58 , pp. 85-201
    • Wächtershäuser, G.1
  • 33
    • 0020646715 scopus 로고
    • Possible limits on the composition of the Archean ocean
    • doi:10.1038/302518a0
    • Walker JCG (1983) Possible limits on the composition of the Archean ocean. Nature 302: 518-520. doi: 10. 1038/302518a0.
    • (1983) Nature , vol.302 , pp. 518-520
    • Walker, J.C.G.1
  • 34
    • 0021753095 scopus 로고
    • Prebiotic formation of energy-rich thioesters from glyceraldehyde and N-acetylcysteine
    • doi:10.1007/BF01809390
    • Weber AL (1984) Prebiotic formation of energy-rich thioesters from glyceraldehyde and N-acetylcysteine. Orig Life Evol Biosph 15: 17-27. doi: 10. 1007/BF01809390.
    • (1984) Orig Life Evol Biosph , vol.15 , pp. 17-27
    • Weber, A.L.1
  • 35
    • 0032104301 scopus 로고    scopus 로고
    • Prebiotic amino acid thioester synthesis: thiol-dependent amino acid synthesis from formose substrates (formaldehyde and glycolaldehyde) and ammonia
    • doi:10.1023/A:1006524818404
    • Weber AL (1998) Prebiotic amino acid thioester synthesis: thiol-dependent amino acid synthesis from formose substrates (formaldehyde and glycolaldehyde) and ammonia. Orig Life Evol Biosph 28: 259-270. doi: 10. 1023/A: 1006524818404.
    • (1998) Orig Life Evol Biosph , vol.28 , pp. 259-270
    • Weber, A.L.1
  • 36
    • 4544323923 scopus 로고    scopus 로고
    • Backbone thioester exchange: a new approach to evaluating higher order structural stability in polypeptides
    • doi:10.1021/ja046891i
    • Woll MG, Gellman SH (2004) Backbone thioester exchange: a new approach to evaluating higher order structural stability in polypeptides. J Am Chem Soc 126: 11172-11174. doi: 10. 1021/ja046891i.
    • (2004) J Am Chem Soc , vol.126 , pp. 11172-11174
    • Woll, M.G.1    Gellman, S.H.2


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