메뉴 건너뛰기




Volumn 25, Issue 8, 2014, Pages 1453-1461

Systematic evaluation and optimization of modification reactions of oligonucleotides with amines and carboxylic acids for the synthesis of dna-encoded chemical libraries

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; AMINES; CARBOXYLIC ACIDS; CHEMICAL MODIFICATION; LIBRARIES; OLIGONUCLEOTIDES;

EID: 84906330932     PISSN: 10431802     EISSN: 15204812     Source Type: Journal    
DOI: 10.1021/bc500212n     Document Type: Article
Times cited : (56)

References (37)
  • 1
    • 84898913565 scopus 로고    scopus 로고
    • DNA-encoded chemical libraries: Advancing beyond conventional small-molecule libraries
    • Franzini, R. M., Neri, D., and Scheuermann, J. (2014) DNA-encoded chemical libraries: advancing beyond conventional small-molecule libraries Acc. Chem. Res. 47, 1247-1255
    • (2014) Acc. Chem. Res. , vol.47 , pp. 1247-1255
    • Franzini, R.M.1    Neri, D.2    Scheuermann, J.3
  • 2
    • 77952543008 scopus 로고    scopus 로고
    • Selecting chemicals: The emerging utility of DNA-encoded libraries
    • Clark, M. A. (2010) Selecting chemicals: the emerging utility of DNA-encoded libraries Curr. Opin. Chem. Biol. 14, 396-403
    • (2010) Curr. Opin. Chem. Biol. , vol.14 , pp. 396-403
    • Clark, M.A.1
  • 3
    • 77951720899 scopus 로고    scopus 로고
    • DNA-encoded chemical libraries: A tool for drug discovery and for chemical biology
    • Scheuermann, J. and Neri, D. (2010) DNA-encoded chemical libraries: a tool for drug discovery and for chemical biology ChemBioChem 11, 931-937
    • (2010) ChemBioChem , vol.11 , pp. 931-937
    • Scheuermann, J.1    Neri, D.2
  • 4
    • 81455140666 scopus 로고    scopus 로고
    • Small-molecule discovery from DNA-encoded chemical libraries
    • Kleiner, R. E., Dumelin, C. E., and Liu, D. R. (2011) Small-molecule discovery from DNA-encoded chemical libraries Chem. Soc. Rev. 40, 5707-5717
    • (2011) Chem. Soc. Rev. , vol.40 , pp. 5707-5717
    • Kleiner, R.E.1    Dumelin, C.E.2    Liu, D.R.3
  • 6
    • 34249296349 scopus 로고    scopus 로고
    • Expanding the scope of PNA-encoded libraries: Divergent synthesis of libraries targeting cysteine, serine and metallo-proteases as well as tyrosine phosphatases
    • Debaene, F., Da Silva, J. A., Pianowski, Z., Duran, F. J., and Winssinger, N. (2007) Expanding the scope of PNA-encoded libraries: divergent synthesis of libraries targeting cysteine, serine and metallo-proteases as well as tyrosine phosphatases Tetrahedron 63, 6577-6586
    • (2007) Tetrahedron , vol.63 , pp. 6577-6586
    • Debaene, F.1    Da Silva, J.A.2    Pianowski, Z.3    Duran, F.J.4    Winssinger, N.5
  • 9
    • 77955792293 scopus 로고    scopus 로고
    • In vitro selection of a DNA-templated small-molecule library reveals a class of macrocyclic kinase inhibitors
    • Kleiner, R. E., Dumelin, C. E., Tiu, G. C., Sakurai, K., and Liu, D. R. (2010) In vitro selection of a DNA-templated small-molecule library reveals a class of macrocyclic kinase inhibitors J. Am. Chem. Soc. 132, 11779-11791
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 11779-11791
    • Kleiner, R.E.1    Dumelin, C.E.2    Tiu, G.C.3    Sakurai, K.4    Liu, D.R.5
  • 15
    • 4644350506 scopus 로고    scopus 로고
    • DNA-templated organic synthesis and selection of a library of macrocycles
    • Gartner, Z. J., Tse, B. N., Grubina, R., Doyon, J. B., Snyder, T. M., and Liu, D. R. (2004) DNA-templated organic synthesis and selection of a library of macrocycles Science 305, 1601-1605
    • (2004) Science , vol.305 , pp. 1601-1605
    • Gartner, Z.J.1    Tse, B.N.2    Grubina, R.3    Doyon, J.B.4    Snyder, T.M.5    Liu, D.R.6
  • 16
    • 55249121613 scopus 로고    scopus 로고
    • Design and synthesis of a novel DNA-encoded chemical library using Diels-Alder cycloadditions
    • Buller, F., Mannocci, L., Zhang, Y., Dumelin, C. E., Scheuermann, J., and Neri, D. (2008) Design and synthesis of a novel DNA-encoded chemical library using Diels-Alder cycloadditions Bioorg. Med. Chem. Lett. 18, 5926-5931
    • (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 5926-5931
    • Buller, F.1    Mannocci, L.2    Zhang, Y.3    Dumelin, C.E.4    Scheuermann, J.5    Neri, D.6
  • 17
    • 0035289779 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings
    • Lipinski, C. A., Lombardo, F., Dominy, B. W., and Feeney, P. J. (2001) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Adv. Drug Delivery Rev. 46, 3-26
    • (2001) Adv. Drug Delivery Rev. , vol.46 , pp. 3-26
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 18
    • 84867095357 scopus 로고    scopus 로고
    • Expanding the scope of PNA-encoded synthesis (PES): Mtt-protected PNA fully orthogonal to fmoc chemistry and a broad array of robust diversity-generating reactions
    • Chouikhi, D., Ciobanu, M., Zambaldo, C., Duplan, V., Barluenga, S., and Winssinger, N. (2012) Expanding the scope of PNA-encoded synthesis (PES): Mtt-protected PNA fully orthogonal to fmoc chemistry and a broad array of robust diversity-generating reactions Chem. - Eur. J. 18, 12698-12704
    • (2012) Chem. - Eur. J. , vol.18 , pp. 12698-12704
    • Chouikhi, D.1    Ciobanu, M.2    Zambaldo, C.3    Duplan, V.4    Barluenga, S.5    Winssinger, N.6
  • 19
  • 20
    • 19344370973 scopus 로고    scopus 로고
    • DNA Display III. Solid-phase organic synthesis on unprotected DNA
    • Halpin, D. R., Lee, J. A., Wrenn, S. J., and Harbury, P. B. (2004) DNA Display III. Solid-phase organic synthesis on unprotected DNA PLOS Biol. 2, e175
    • (2004) PLOS Biol. , vol.2 , pp. 175
    • Halpin, D.R.1    Lee, J.A.2    Wrenn, S.J.3    Harbury, P.B.4
  • 21
    • 0036263805 scopus 로고    scopus 로고
    • Expanding the reaction scope of DNA-templated synthesis
    • Gartner, Z. J., Kanan, M. W., and Liu, D. R. (2002) Expanding the reaction scope of DNA-templated synthesis Angew. Chem., Int. Ed. 41, 1796-1800
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 1796-1800
    • Gartner, Z.J.1    Kanan, M.W.2    Liu, D.R.3
  • 22
    • 13644254493 scopus 로고    scopus 로고
    • DNA-templated functional group transformations enable sequence-programmed synthesis using small-molecule reagents
    • Sakurai, K., Snyder, T. M., and Liu, D. R. (2005) DNA-templated functional group transformations enable sequence-programmed synthesis using small-molecule reagents J. Am. Chem. Soc. 127, 1660-1661
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 1660-1661
    • Sakurai, K.1    Snyder, T.M.2    Liu, D.R.3
  • 23
    • 0034846039 scopus 로고    scopus 로고
    • Chemical cross-linking of peptides derived from RecA with single-stranded oligonucleotides containing 5-formyl-2′-deoxyuridine
    • Sugiyama, T., Kittaka, A., Takayama, H., Tomioka, M., Ida, Y., and Kuroda, R. (2001) Chemical cross-linking of peptides derived from RecA with single-stranded oligonucleotides containing 5-formyl-2′-deoxyuridine Nucleosides Nucleotides Nucleic Acids 20, 1079-83
    • (2001) Nucleosides Nucleotides Nucleic Acids , vol.20 , pp. 1079-1083
    • Sugiyama, T.1    Kittaka, A.2    Takayama, H.3    Tomioka, M.4    Ida, Y.5    Kuroda, R.6
  • 24
    • 84858988466 scopus 로고    scopus 로고
    • Synthesis of aldehyde-linked nucleotides and DNA and their bioconjugations with lysine and peptides through reductive amination
    • Raindlova, V., Pohl, R., and Hocek, M. (2012) Synthesis of aldehyde-linked nucleotides and DNA and their bioconjugations with lysine and peptides through reductive amination Chem. - Eur. J. 18, 4080-4087
    • (2012) Chem. - Eur. J. , vol.18 , pp. 4080-4087
    • Raindlova, V.1    Pohl, R.2    Hocek, M.3
  • 26
    • 1842556433 scopus 로고    scopus 로고
    • Versatile 5′-functionalization of oligonucleotides on solid support: Amines, azides, thiols, and thioethers via phosphorus chemistry
    • Miller, G. P. and Kool, E. T. (2004) Versatile 5′-functionalization of oligonucleotides on solid support: amines, azides, thiols, and thioethers via phosphorus chemistry J. Org. Chem. 69, 2404-2410
    • (2004) J. Org. Chem. , vol.69 , pp. 2404-2410
    • Miller, G.P.1    Kool, E.T.2
  • 27
    • 0028568952 scopus 로고
    • Selective chemical autoligation on a double-stranded DNA template
    • Herrlein, M. K. and Letsinger, R. L. (1994) Selective chemical autoligation on a double-stranded DNA template Nucleic Acids Res. 22, 5076-5078
    • (1994) Nucleic Acids Res. , vol.22 , pp. 5076-5078
    • Herrlein, M.K.1    Letsinger, R.L.2
  • 28
    • 0032535181 scopus 로고    scopus 로고
    • Conjugation of oligonucleotides via an electrophilic tether: N-chloroacetamidohexyl phosphoramidite reagent
    • Guzaev, A. and Manoharan, M. (1998) Conjugation of oligonucleotides via an electrophilic tether: N-chloroacetamidohexyl phosphoramidite reagent Bioorg. Med. Chem. Lett. 8, 3671-3676
    • (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 3671-3676
    • Guzaev, A.1    Manoharan, M.2
  • 29
    • 0032780654 scopus 로고    scopus 로고
    • Synthesis of oligonucleotide conjugates with the aid of N-chloroacetamidohexyl phosphoramidite reagent
    • Guzaev, A. and Manoharan, M. (1999) Synthesis of oligonucleotide conjugates with the aid of N-chloroacetamidohexyl phosphoramidite reagent Nucleosides Nucleotides Nucleic Acids 18, 1455-1456
    • (1999) Nucleosides Nucleotides Nucleic Acids , vol.18 , pp. 1455-1456
    • Guzaev, A.1    Manoharan, M.2
  • 31
    • 0028233019 scopus 로고
    • Fast cleavage and deprotection of oligonucleotides
    • Reddy, M. P., Hanna, N. B., and Farooqui, F. (1994) Fast cleavage and deprotection of oligonucleotides Tetrahedron Lett. 35, 4311-4314
    • (1994) Tetrahedron Lett. , vol.35 , pp. 4311-4314
    • Reddy, M.P.1    Hanna, N.B.2    Farooqui, F.3
  • 32
    • 0035945239 scopus 로고    scopus 로고
    • Attachment of benzaldehyde-modified oligodeoxynucleotide probes to semicarbazide-coated glass
    • Podyminogin, M. A., Lukhtanov, E. A., and Reed, M. W. (2001) Attachment of benzaldehyde-modified oligodeoxynucleotide probes to semicarbazide-coated glass Nucleic Acids Res. 29, 5090-5098
    • (2001) Nucleic Acids Res. , vol.29 , pp. 5090-5098
    • Podyminogin, M.A.1    Lukhtanov, E.A.2    Reed, M.W.3
  • 33
    • 0344105390 scopus 로고
    • An addition reaction specific for uridine and guanosine nucleosides and its application to the modification of ribonuclease action
    • Gilham, P. T. (1962) An addition reaction specific for uridine and guanosine nucleosides and its application to the modification of ribonuclease action J. Am. Chem. Soc. 84, 687-688
    • (1962) J. Am. Chem. Soc. , vol.84 , pp. 687-688
    • Gilham, P.T.1
  • 34
    • 0014172260 scopus 로고
    • The reversible chemical modification of uracil, thymine, and guanine nucleotides and the modification of the action of ribonuclease on ribonucleic acid
    • Ho, N. W. and Gilham, P. T. (1967) The reversible chemical modification of uracil, thymine, and guanine nucleotides and the modification of the action of ribonuclease on ribonucleic acid Biochemistry 6, 3632-3639
    • (1967) Biochemistry , vol.6 , pp. 3632-3639
    • Ho, N.W.1    Gilham, P.T.2
  • 35
    • 62449152302 scopus 로고    scopus 로고
    • Amide bond formation: Beyond the myth of coupling reagents
    • Valeur, E. and Bradley, M. (2009) Amide bond formation: beyond the myth of coupling reagents Chem. Soc. Rev. 38, 606-631
    • (2009) Chem. Soc. Rev. , vol.38 , pp. 606-631
    • Valeur, E.1    Bradley, M.2
  • 36
    • 0034643993 scopus 로고    scopus 로고
    • A "traceless" Staudinger ligation for the chemoselective synthesis of amide bonds
    • Saxon, E., Armstrong, J. I., and Bertozzi, C. R. (2000) A "traceless" Staudinger ligation for the chemoselective synthesis of amide bonds Org. Lett. 2, 2141-2143
    • (2000) Org. Lett. , vol.2 , pp. 2141-2143
    • Saxon, E.1    Armstrong, J.I.2    Bertozzi, C.R.3
  • 37
    • 33746190644 scopus 로고    scopus 로고
    • Chemoselective amide ligations by decarboxylative condensations of N -alkylhydroxylamines and α-ketoacids
    • Bode, J. W., Fox, R. M., and Baucom, K. D. (2006) Chemoselective amide ligations by decarboxylative condensations of N -alkylhydroxylamines and α-ketoacids Angew. Chem. Int. Ed. 45, 1248-1252
    • (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 1248-1252
    • Bode, J.W.1    Fox, R.M.2    Baucom, K.D.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.