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Volumn 16, Issue 9, 2015, Pages 21858-21872

Simultaneous disulfide and boronic acid ester exchange in dynamic combinatorial libraries

Author keywords

Boronic acid esters; Boronic acids; Disulfides; Dynamic combinatorial chemistry; Reversible chemical reactions; Supramolecular chemistry; Thiols

Indexed keywords

BORONIC ACID DERIVATIVE; DISULFIDE; ESTER;

EID: 84941342371     PISSN: 16616596     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms160921858     Document Type: Article
Times cited : (23)

References (34)
  • 2
  • 3
    • 84859896006 scopus 로고    scopus 로고
    • History and Principles of Dynamic Combinatorial Chemistry
    • Reek, J.N.H., Otto, S., Eds.; Wiley-VCH: Weinheim, Germany
    • Beeren, S.R.; Sanders, J.K.M. History and Principles of Dynamic Combinatorial Chemistry. In Dynamic Combinatorial Chemistry; Reek, J.N.H., Otto, S., Eds.; Wiley-VCH: Weinheim, Germany, 2010
    • (2010) Dynamic Combinatorial Chemistry
    • Beeren, S.R.1    Sanders, J.2
  • 5
    • 84897625761 scopus 로고    scopus 로고
    • Disulfide exchange: Exposing supramolecular reactivity through dynamic covalent chemistry
    • Black, S.P.; Sanders, J.K.M.; Stefankiewich, A.R. Disulfide exchange: Exposing supramolecular reactivity through dynamic covalent chemistry. Chem. Soc. Rev. 2014, 43, 1861–1872
    • (2014) Chem. Soc. Rev , vol.43 , pp. 1861-1872
    • Black, S.P.1    Sanders, J.2    Stefankiewich, A.R.3
  • 6
    • 18244373223 scopus 로고    scopus 로고
    • Amplification of acetylcholine-binding catenanes from dynamic combinatorial libraries
    • Lam, R.T.; Belenguer, A.; Roberts, S.L.; Maumann, C.; Jarrosson, T.; Otto, S.; Sanders, J.K.M. Amplification of acetylcholine-binding catenanes from dynamic combinatorial libraries. Science 2005, 308, 667–669
    • (2005) Science , vol.308 , pp. 667-669
    • Lam, R.T.1    Belenguer, A.2    Roberts, S.L.3    Maumann, C.4    Jarrosson, T.5    Otto, S.6    Sanders, J.7
  • 8
    • 38049066994 scopus 로고    scopus 로고
    • Self-assembly in systems of subcomponents: Simple rules, subtle consequences
    • Sarma, R.J.; Nitschke, J.R. Self-assembly in systems of subcomponents: Simple rules, subtle consequences. Angew. Chem. Int. Ed. 2008, 47, 377–380
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 377-380
    • Sarma, R.J.1    Nitschke, J.R.2
  • 9
    • 0035852702 scopus 로고    scopus 로고
    • Double-level “orthogonal” dynamic combinatorial libraries on transition metal template
    • Goral, V.; Nelen, M.I.; Eliseev, A.V.; Lehn, J.-M. Double-level “orthogonal” dynamic combinatorial libraries on transition metal template. Proc. Natl. Acad. Sci. USA 2001, 98, 1347–1352
    • (2001) Proc. Natl. Acad. Sci. USA , vol.98 , pp. 1347-1352
    • Goral, V.1    Nelen, M.I.2    Eliseev, A.V.3    Lehn, J.-M.4
  • 10
    • 18044382132 scopus 로고    scopus 로고
    • Expanding diversity in dynamic combinatorial libraries: Simultaneous exchange of disulfide and thioester linkages
    • Leclaire, J.; Vial, L.; Otto, S.; Sanders, J.K.M. Expanding diversity in dynamic combinatorial libraries: Simultaneous exchange of disulfide and thioester linkages. Chem. Commun. 2005, doi:10.1039/B500638D.
    • (2005) Chem. Commun
    • Leclaire, J.1    Vial, L.2    Otto, S.3    Sanders, J.4
  • 11
    • 55349124942 scopus 로고    scopus 로고
    • Orthogonal or simultaneous use of disulfide and hydrazone exchange in dynamic covalent chemistry in aqueous solution
    • Rodriguez-Docampo, Z.; Otto, S. Orthogonal or simultaneous use of disulfide and hydrazone exchange in dynamic covalent chemistry in aqueous solution. Chem. Commun. 2008, doi:10.1039/B808725C.
    • (2008) Chem. Commun
    • Rodriguez-Docampo, Z.1    Otto, S.2
  • 12
    • 55349093946 scopus 로고    scopus 로고
    • Covalent double level dynamic combinatorial libraries: Selectively addressable exchange processes
    • Orrillo, A.G.; Escalante, A.M.; Furlan, R.L.E. Covalent double level dynamic combinatorial libraries: Selectively addressable exchange processes. Chem. Commun. 2008, doi:10.1039/B808565J.
    • (2008) Chem. Commun
    • Orrillo, A.G.1    Escalante, A.M.2    Furlan, R.3
  • 13
    • 77954546907 scopus 로고    scopus 로고
    • Simultaneous and orthogonal covalent exchange processes in dynamic combinatorial libraries
    • Escalante, A.M.; Orrillo, A.G.; Escalante, A.M.; Furlan, R.L.E. Simultaneous and orthogonal covalent exchange processes in dynamic combinatorial libraries. J. Comb. Chem. 2010, 12, 410–413
    • (2010) J. Comb. Chem , vol.12 , pp. 410-413
    • Escalante, A.M.1    Orrillo, A.G.2    Escalante, A.M.3    Furlan, R.4
  • 14
    • 53249147379 scopus 로고    scopus 로고
    • An iminoboronate construction set for subcomponent self-assembly
    • Hutin, M.; Bernardinelli, G.; Nitschke, J.R. An iminoboronate construction set for subcomponent self-assembly. Chem. Eur. J. 2008, 14, 4585–4593
    • (2008) Chem. Eur. J , vol.14 , pp. 4585-4593
    • Hutin, M.1    Bernardinelli, G.2    Nitschke, J.R.3
  • 15
    • 22244481543 scopus 로고    scopus 로고
    • Disulfide exchange in hydrogen-bonded cyclic assemblies: Stereochemical self-selection in double dynamic chemistry
    • Ten Cate, A.T.; Dankers, P.Y.W.; Sijbesma, R.P.; Meijer, E.W. Disulfide exchange in hydrogen-bonded cyclic assemblies: Stereochemical self-selection in double dynamic chemistry. J. Org. Chem. 2005, 70, 5799–5803
    • (2005) J. Org. Chem , vol.70 , pp. 5799-5803
    • Ten Cate, A.T.1    Dankers, P.2    Sijbesma, R.P.3    Meijer, E.W.4
  • 16
    • 36649016862 scopus 로고    scopus 로고
    • Disulfides, imines and metal coordination within a single system: Interplay between three dynamic equilibria
    • Sarma, R.J.; Otto, S.; Nitschke, J.R. Disulfides, imines and metal coordination within a single system: Interplay between three dynamic equilibria. Chem. Eur. J. 2007, 13, 9542–9546
    • (2007) Chem. Eur. J , vol.13 , pp. 9542-9546
    • Sarma, R.J.1    Otto, S.2    Nitschke, J.R.3
  • 17
    • 2942746446 scopus 로고    scopus 로고
    • A new method for the synthesis of boronate macrocycles
    • Christinat, N.; Scopelliti, R.; Severin, K. A new method for the synthesis of boronate macrocycles. Chem. Commun. 2004, 1158–1159
    • (2004) Chem. Commun , pp. 1158-1159
    • Christinat, N.1    Scopelliti, R.2    Severin, K.3
  • 18
    • 84868691251 scopus 로고    scopus 로고
    • Multicomponent assembly of macrocycles and polymers by coordination of pyridyl ligands to 1,4-bis(Benzodioxaorole)benzene
    • Icli, B.; Solari, A.; Kilbas, B.; Scopelliti, R.; Severin, K. Multicomponent assembly of macrocycles and polymers by coordination of pyridyl ligands to 1,4-bis(benzodioxaorole)benzene. Chem. Eur. J. 2012, 18, 14867–14874
    • (2012) Chem. Eur. J , vol.18 , pp. 14867-14874
    • Icli, B.1    Solari, A.2    Kilbas, B.3    Scopelliti, R.4    Severin, K.5
  • 19
    • 84877298929 scopus 로고    scopus 로고
    • Self-assembly of arylboronate esters with pyridyl side chains
    • Sheepwash, E.; Zhou, K.; Scopelliti, R.; Severin, K. Self-assembly of arylboronate esters with pyridyl side chains. Eur. J. Inorg. Chem. 2013, 2013, 2558–2563
    • (2013) Eur. J. Inorg. Chem , vol.2013 , pp. 2558-2563
    • Sheepwash, E.1    Zhou, K.2    Scopelliti, R.3    Severin, K.4
  • 20
    • 41949112105 scopus 로고    scopus 로고
    • Multicomponent assembly of boronic acid based macrocycles and cages
    • Christinat, N.; Scopelliti, R.; Severin, K. Multicomponent assembly of boronic acid based macrocycles and cages. Angew. Chem. Int. Ed. 2008, 47, 1848–1852
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 1848-1852
    • Christinat, N.1    Scopelliti, R.2    Severin, K.3
  • 21
    • 76249131765 scopus 로고    scopus 로고
    • A synthetic small molecule that can walk down a track
    • Von Delius, M.; Geertsema, E.M.; Leigh, D.A. A synthetic small molecule that can walk down a track. Nat. Chem. 2010, 2, 96–101
    • (2010) Nat. Chem , vol.2 , pp. 96-101
    • Von Delius, M.1    Geertsema, E.M.2    Leigh, D.A.3
  • 22
    • 72449198494 scopus 로고    scopus 로고
    • Guest-induced dynamic self-assembly of two diastereomeric cage-like boronic esters
    • Takahagi, H.; Fujibe, S.; Iwasawa, N. Guest-induced dynamic self-assembly of two diastereomeric cage-like boronic esters. Chem. Eur. J. 2009, 15, 13327–13330
    • (2009) Chem. Eur. J , vol.15 , pp. 13327-13330
    • Takahagi, H.1    Fujibe, S.2    Iwasawa, N.3
  • 23
    • 34347243104 scopus 로고    scopus 로고
    • Boronic esters as a system for crystallization-induced dynamic self-assembly equipped with an “on-off” switch for equilibration
    • Iwasawa, N.; Takahagi, H. Boronic esters as a system for crystallization-induced dynamic self-assembly equipped with an “on-off” switch for equilibration. J. Am. Chem. Soc. 2007, 129, 7754–7755
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 7754-7755
    • Iwasawa, N.1    Takahagi, H.2
  • 24
    • 84863658767 scopus 로고    scopus 로고
    • Guest-induced self-assembly of a macrocyclic boronic ester containing diarylethene units: Enhancement of photoresponsivity
    • Iwasawa, N.; Takahagi, H.; Ono, K.; Fujii, K.; Uekusa, H. Guest-induced self-assembly of a macrocyclic boronic ester containing diarylethene units: Enhancement of photoresponsivity. Chem. Commun. 2012, 48, 7477–7479
    • (2012) Chem. Commun , vol.48 , pp. 7477-7479
    • Iwasawa, N.1    Takahagi, H.2    Ono, K.3    Fujii, K.4    Uekusa, H.5
  • 25
    • 78649943741 scopus 로고    scopus 로고
    • Crystallization-controlled dynamic self-assembly and an on/off switch for equilibration using boronic ester formation
    • Takahagi, H.; Iwasawa, N. Crystallization-controlled dynamic self-assembly and an on/off switch for equilibration using boronic ester formation. Chem. Eur. J. 2010, 16, 13680–13688
    • (2010) Chem. Eur. J , vol.16 , pp. 13680-13688
    • Takahagi, H.1    Iwasawa, N.2
  • 26
    • 37049013120 scopus 로고    scopus 로고
    • Ion pair-driven heterodimeric capsule based on boronate esterification: Construction and the dynamic behavior
    • Kataoka, K.; James, T.D.; Kubo, Y. Ion pair-driven heterodimeric capsule based on boronate esterification: Construction and the dynamic behavior. J. Am. Chem. Soc. 2007, 129, 15126–15127
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 15126-15127
    • Kataoka, K.1    James, T.D.2    Kubo, Y.3
  • 27
    • 62349122413 scopus 로고    scopus 로고
    • Amine-triggered molecular capsules using dynamic boronate esterification
    • Kataoka, K.; Okuyama, S.; Minami, T.; James, T.D.; Kubo, Y. Amine-triggered molecular capsules using dynamic boronate esterification. Chem. Commun. 2009, doi:10.1039/B900102F.
    • (2009) Chem. Commun
    • Kataoka, K.1    Okuyama, S.2    Minami, T.3    James, T.D.4    Kubo, Y.5
  • 28
    • 79959547430 scopus 로고    scopus 로고
    • An approach to enzyme inhibition employing reversible boronate ester formation
    • Leung, I.K.H.; Brown, T.; Schofield, C.J., Jr.; Claridge, T.D.W. An approach to enzyme inhibition employing reversible boronate ester formation. Med. Chem. Commun. 2011, 2, 390–395
    • (2011) Med. Chem. Commun , vol.2 , pp. 390-395
    • Leung, I.1    Brown, T.2    Schofield, C.J.3    Claridge, T.4
  • 29
    • 0242500379 scopus 로고    scopus 로고
    • Selection and amplification of a catalyst from a dynamic combinatorial library
    • Brisig, B.; Sanders, J.K.M.; Otto, S. Selection and amplification of a catalyst from a dynamic combinatorial library. Angew. Chem. Int. Ed. 2003, 42, 1270–1273
    • (2003) Angew. Chem. Int. Ed , vol.42 , pp. 1270-1273
    • Brisig, B.1    Sanders, J.2    Otto, S.3
  • 30
    • 24044533497 scopus 로고    scopus 로고
    • A catalyst for an acetal hydrolysis reaction from a dynamic combinatorial library
    • Vial, L.; Sanders, J.K.M.; Otto, S. A catalyst for an acetal hydrolysis reaction from a dynamic combinatorial library. New J. Chem. 2015, 29, 1001–1003
    • (2015) New J. Chem , vol.29 , pp. 1001-1003
    • Vial, L.1    Sanders, J.2    Otto, S.3
  • 31
  • 32
    • 17444363360 scopus 로고    scopus 로고
    • Dynamic synthesis of a macrocycle containing a porphyrin and an electron donor
    • Kieran, A.L.; Pascu, S.I.; Jarrosson, T.; Gunter, M.J.; Sanders, J.K.M. Dynamic synthesis of a macrocycle containing a porphyrin and an electron donor. Chem. Commun. 2005, doi:10.1039/B418811J.
    • (2005) Chem. Commun
    • Kieran, A.L.1    Pascu, S.I.2    Jarrosson, T.3    Gunter, M.J.4    Sanders, J.5
  • 33
    • 0242609897 scopus 로고    scopus 로고
    • Dynamic combinatorial libraries of metalloporphyrins: Template amplification of disulfide-linked oligomers
    • Kieran, A.L.; Bond, A.D.; Belenguer, A.M.; Sanders, J.K.M. Dynamic combinatorial libraries of metalloporphyrins: Template amplification of disulfide-linked oligomers. Chem. Commun. 2003, doi:10.1039/B310438A.
    • (2003) Chem. Commun
    • Kieran, A.L.1    Bond, A.D.2    Belenguer, A.M.3    Sanders, J.4
  • 34
    • 0000395659 scopus 로고
    • Dynamic processes in boranes, borane complexes, carboranes, and related compounds
    • Beall, H.; Bushweller, H. Dynamic processes in boranes, borane complexes, carboranes, and related compounds. Chem. Rev. 1973, 73, 465–486.
    • (1973) Chem. Rev , vol.73 , pp. 465-486
    • Beall, H.1    Bushweller, H.2


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