메뉴 건너뛰기




Volumn , Issue SUPPL. 35, 2008, Pages

Release of DNA oligonucleotides and their conjugates from controlled-pore glass under thermolytic conditions

Author keywords

Deoxyribonucleoside phosphorodiamidites; DNA oligonucleotides conjugates; Modified CPG support; Solid phase synthesis; Thermolytic conditions

Indexed keywords

2N ISOBUTYRYL 5' O (4,4' DIMETHOXYTRITYL) 3' O BIS(N,N DIISOPROPYLAMINO)PHOSPHINYL 2' DEOXYGUANOSINE; 4N BENZOYL 5' O (4,4' DIMETHOXYTRITYL) 3' O BIS(N,N DIISOPROPYLAMINO)PHOSPHINYL 2' DEOXYCYTIDINE; 5' O (4,4' DIMETHOXYTRITYL) 3' O BIS(N,N DIISOPROPYLAMINO)PHOSPHINYL 2' DEOXYTHYMIDINE; 6N BENZOYL 5' O (4,4' DIMETHOXYTRITYL) 3' O BIS(N,N DIISOPROPYLAMINO)PHOSPHINYL 2' DEOXYADENOSINE; GLASS; OLIGONUCLEOTIDE; PHOSPHORAMIDOUS ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 58849095800     PISSN: 19349270     EISSN: 19349289     Source Type: Journal    
DOI: 10.1002/0471142700.nc0317s35     Document Type: Review
Times cited : (5)

References (25)
  • 1
    • 0342695291 scopus 로고    scopus 로고
    • Attachment of reporter and conjugate groups to DNA
    • In (D. Barton, K. Nakanishi, O. Meth-Cohn, and E.T. Kool, eds.) Elsevier Science Publishing, New York
    • Beaucage, S.L. 1999. Attachment of reporter and conjugate groups to DNA. In Comprehensive Natural Products Chemistry, Volume 7: DNA and Aspects of Molecular Biology (D. Barton, K. Nakanishi, O. Meth-Cohn, and E.T. Kool, eds.) pp. 153-249. Elsevier Science Publishing, New York.
    • (1999) Comprehensive Natural Products Chemistry, Volume 7: DNA and Aspects of Molecular Biology , pp. 153-249
    • Beaucage, S.L.1
  • 2
    • 0026606239 scopus 로고
    • Advances in the synthesis of oligonucleotides by the phosphoramidite approach
    • Beaucage, S.L. and Iyer, R.P. 1992. Advances in the synthesis of oligonucleotides by the phosphoramidite approach. Tetrahedron 48:2223-2311.
    • (1992) Tetrahedron , vol.48 , pp. 2223-2311
    • Beaucage, S.L.1    Iyer, R.P.2
  • 3
    • 0024506335 scopus 로고
    • Studies on the role of tetrazole in the activation of phosphoramidites
    • Berner, S., Mühlegger, K., and Seliger, H. 1989. Studies on the role of tetrazole in the activation of phosphoramidites. Nucleic Acids Res. 17:853-864.
    • (1989) Nucleic Acids Res. , vol.17 , pp. 853-864
    • Berner, S.1    Mühlegger, K.2    Seliger, H.3
  • 4
    • 0029764164 scopus 로고    scopus 로고
    • Cleavage of oligodeoxyribonucleotides from controlledpore glass supports and their rapid deprotection by gaseous amines
    • Boal, J.H., Wilk, A., Harindranath, N., Max, E.E., Kempe, T., and Beaucage, S.L. 1996. Cleavage of oligodeoxyribonucleotides from controlledpore glass supports and their rapid deprotection by gaseous amines. Nucleic Acids Res. 24:3115-3117.
    • (1996) Nucleic Acids Res. , vol.24 , pp. 3115-3117
    • Boal, J.H.1    Wilk, A.2    Harindranath, N.3    Max, E.E.4    Kempe, T.5    Beaucage, S.L.6
  • 5
    • 0346992398 scopus 로고    scopus 로고
    • Thermolytic properties of 3-(2-pyridyl)-1-propyl and 2-[N-methyl-N- (2-pyridyl)]aminoethyl phosphate/thiophosphate protecting groups in solid-phase synthesis of oligodeoxyribonucleotides
    • Ciéslak, J. and Beaucage, S.L. 2003. Thermolytic properties of 3-(2-pyridyl)-1-propyl and 2-[N-methyl-N-(2-pyridyl)]aminoethyl phosphate/thiophosphate protecting groups in solid-phase synthesis of oligodeoxyribonucleotides. J. Org. Chem. 68:10123-10129.
    • (2003) J. Org. Chem. , vol.68 , pp. 10123-10129
    • Ciéslak, J.1    Beaucage, S.L.2
  • 6
    • 12144287950 scopus 로고    scopus 로고
    • The thermolytic 4-methylthio-1-butyl group for phosphate/thiophosphate protection in solid-phase synthesis of DNA oligonucleotides
    • Ciéslak, J., Grajkowski, A., Livengood, V., and Beaucage, S.L. 2004. The thermolytic 4-methylthio-1-butyl group for phosphate/ thiophosphate protection in solid-phase synthesis of DNA oligonucleotides. J. Org. Chem. 69:2509-2515.
    • (2004) J. Org. Chem. , vol.69 , pp. 2509-2515
    • Ciéslak, J.1    Grajkowski, A.2    Livengood, V.3    Beaucage, S.L.4
  • 8
    • 0035799851 scopus 로고    scopus 로고
    • The 2-(N-formyl-N-methyl)aminoethyl group as a potential phosphate/ thiophosphate protecting group in solid-phase oligodeoxyribonucleotide synthesis
    • Grajkowski, A., Wilk, A., Chmielewski, M.K., Phillips, L.R., and Beaucage, S.L. 2001. The 2-(N-formyl-N-methyl)aminoethyl group as a potential phosphate/thiophosphate protecting group in solid-phase oligodeoxyribonucleotide synthesis. Org. Lett. 3:1287-1290.
    • (2001) Org. Lett. , vol.3 , pp. 1287-1290
    • Grajkowski, A.1    Wilk, A.2    Chmielewski, M.K.3    Phillips, L.R.4    Beaucage, S.L.5
  • 9
    • 33846935981 scopus 로고    scopus 로고
    • Solid-phase synthesis of thermolytic DNA oligonucleotides functionalized with a single 4-hydroxy-1-butyl or 4-phosphato/-thiophosphato-1-butyl thiophosphate protecting group
    • Grajkowski, A., Ausín, C., Kauffman, J.S., Snyder, J., Hess, S., Lloyd, J.R., and Beaucage, S.L. 2007. Solid-phase synthesis of thermolytic DNA oligonucleotides functionalized with a single 4-hydroxy-1-butyl or 4-phosphato/-thiophosphato-1-butyl thiophosphate protecting group. J. Org. Chem. 72:805-815.
    • (2007) J. Org. Chem. , vol.72 , pp. 805-815
    • Grajkowski, A.1    Ausín, C.2    Kauffman, J.S.3    Snyder, J.4    Hess, S.5    Lloyd, J.R.6    Beaucage, S.L.7
  • 10
    • 50249134308 scopus 로고    scopus 로고
    • Thermolytic release of covalently linked DNA oligonucleotides and their conjugates from controlled-pore glass at near neutral pH
    • Grajkowski, A., Ciéslak, J., Kauffman, J.S., Duff, R.J., Norris, S., Freedberg, D., and Beaucage, S.L. 2008. Thermolytic release of covalently linked DNA oligonucleotides and their conjugates from controlled-pore glass at near neutral pH. Bioconjugate Chem. 19:1696-1706.
    • (2008) Bioconjugate Chem. , vol.19 , pp. 1696-1706
    • Grajkowski, A.1    Ciéslak, J.2    Kauffman, J.S.3    Duff, R.J.4    Norris, S.5    Freedberg, D.6    Beaucage, S.L.7
  • 11
    • 0016856713 scopus 로고
    • Levulinic esters. Alcohol protecting group applicable to some nucleosides
    • Hassner, A., Strand, G., Rubinstein, M., and Patchornik, A. 1975. Levulinic esters. Alcohol protecting group applicable to some nucleosides. J. Am. Chem. Soc. 97:1614-1615.
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 1614-1615
    • Hassner, A.1    Strand, G.2    Rubinstein, M.3    Patchornik, A.4
  • 12
    • 0025161168 scopus 로고
    • The automated synthesis of sulfur-containing oligodeoxyribonucleotides using 3H-1,2-benzodithiol-3-one 1,1-dioxide as a sulfur-transfer reagent
    • Iyer, R.P., Phillips, L.R., Egan, W., Regan, J.B., and Beaucage, S.L. 1990. The automated synthesis of sulfur-containing oligodeoxyribonucleotides using 3H-1,2-benzodithiol-3-one 1,1-dioxide as a sulfur-transfer reagent. J. Org. Chem. 55:4693-4699.
    • (1990) J. Org. Chem. , vol.55 , pp. 4693-4699
    • Iyer, R.P.1    Phillips, L.R.2    Egan, W.3    Regan, J.B.4    Beaucage, S.L.5
  • 13
    • 34249794857 scopus 로고    scopus 로고
    • Template-directed oligonucleotide strand ligation, covalent intramolecular DNA circularization and catenation using click chemistry
    • Kumar, R., El-Sagheer, A., Tumpane, J., Lincoln, P., Wilhelmsson, L.M., and Brown, T. 2007. Template-directed oligonucleotide strand ligation, covalent intramolecular DNA circularization and catenation using click chemistry. J. Am. Chem. Soc. 129:6859-6864.
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 6859-6864
    • Kumar, R.1    El-Sagheer, A.2    Tumpane, J.3    Lincoln, P.4    Wilhelmsson, L.M.5    Brown, T.6
  • 14
    • 0001612798 scopus 로고
    • Oligonucleotide synthesis on a polymer support
    • Letsinger, R.L. and Mahadevan, V. 1965. Oligonucleotide synthesis on a polymer support. J. Am. Chem. Soc. 87:3526-3527.
    • (1965) J. Am. Chem. Soc. , vol.87 , pp. 3526-3527
    • Letsinger, R.L.1    Mahadevan, V.2
  • 15
    • 0014023626 scopus 로고
    • Stepwise synthesis of oligodeoxyribonucleotides on an insoluble polymer support
    • Letsinger, R.L. and Mahadevan, V. 1966. Stepwise synthesis of oligodeoxyribonucleotides on an insoluble polymer support. J. Am. Chem. Soc. 88:5319-5324.
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 5319-5324
    • Letsinger, R.L.1    Mahadevan, V.2
  • 16
    • 0343959655 scopus 로고
    • A new and versatile approach to the preparation of valuable deoxynucleoside 3′-phosphite intermediates
    • Marugg, J.E., Burik, A., Tromp, M., van der Marel, G.A., and van Boom, J.H. 1986. A new and versatile approach to the preparation of valuable deoxynucleoside 3′-phosphite intermediates. Tetrahedron Lett. 27:2271-2274.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 2271-2274
    • Marugg, J.E.1    Burik, A.2    Tromp, M.3    van der Marel, G.A.4    van Boom, J.H.5
  • 17
    • 20744456789 scopus 로고
    • Solid phase peptide synthesis. I. The synthesis of a tetrapeptide
    • Merrifield, R.B. 1963. Solid phase peptide synthesis. I. The synthesis of a tetrapeptide. J. Am. Chem. Soc. 85:2149-2154.
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 2149-2154
    • Merrifield, R.B.1
  • 18
    • 0013844446 scopus 로고
    • Automated synthesis of peptides
    • Merrifield, R.B. 1965. Automated synthesis of peptides. Science 150:178-185.
    • (1965) Science , vol.150 , pp. 178-185
    • Merrifield, R.B.1
  • 19
    • 0000839769 scopus 로고
    • Large-scale preparation of the sulfur-transfer reagent 3H-1,2- benzodithiol-3-one 1,1-dioxide
    • Regan, J.B., Phillips, L.R., and Beaucage, S.L. 1992. Large-scale preparation of the sulfur-transfer reagent 3H-1,2-benzodithiol-3-one 1,1-dioxide. Org. Prep. Proc. Int. 24:488-492.
    • (1992) Org. Prep. Proc. Int. , vol.24 , pp. 488-492
    • Regan, J.B.1    Phillips, L.R.2    Beaucage, S.L.3
  • 20
    • 0034498920 scopus 로고    scopus 로고
    • Solid-phase oligosaccharide synthesis and combinatorial carbohydrate libraries
    • Seeberger, P.H. and Haase,W.-C. 2000. Solid-phase oligosaccharide synthesis and combinatorial carbohydrate libraries. Chem. Rev. 100:4349-4393.
    • (2000) Chem. Rev. , vol.100 , pp. 4349-4393
    • Seeberger, P.H.1    Haase, W.-C.2
  • 21
    • 26044440288 scopus 로고    scopus 로고
    • Automated synthesis of oligosaccharides as a basis for drug discovery
    • Seeberger, P.H. and Werz, D.B. 2005. Automated synthesis of oligosaccharides as a basis for drug discovery. Nature Rev. Drug Discov. 4:751-763.
    • (2005) Nature Rev. Drug Discov. , vol.4 , pp. 751-763
    • Seeberger, P.H.1    Werz, D.B.2
  • 22
    • 0042744934 scopus 로고    scopus 로고
    • Solid-supported synthesis of oligomeric bioconjugates
    • Virta, P., Katajisto, J., Niittymäki, T., and Lönnberg, H. 2003. Solid-supported synthesis of oligomeric bioconjugates. Tetrahedron 59:5137-5174.
    • (2003) Tetrahedron , vol.59 , pp. 5137-5174
    • Virta, P.1    Katajisto, J.2    Niittymäki, T.3    Lönnberg, H.4
  • 23
    • 0034653728 scopus 로고    scopus 로고
    • Deoxyribonucleoside cyclic N-acylphosphoramidites as a new class of monomers for the stereocontrolled synthesis of oligothymidylyl- and oligocytidylyl-phosphorothioates
    • Wilk, A., Grajkowski, A., Phillips, L.R., and Beaucage, S.L. 2000. Deoxyribonucleoside cyclic N-acylphosphoramidites as a new class of monomers for the stereocontrolled synthesis of oligothymidylyl- and oligocytidylyl-phosphorothioates. J. Am.Chem. Soc. 122:2149-2156.
    • (2000) J. Am.Chem. Soc. , vol.122 , pp. 2149-2156
    • Wilk, A.1    Grajkowski, A.2    Phillips, L.R.3    Beaucage, S.L.4
  • 24
    • 0035855342 scopus 로고    scopus 로고
    • The 4-oxopentyl group, as a labile phos-phate/thiophosphate protecting group for synthetic oligodeoxyribonucleotides
    • Wilk, A., Chmielewski, M.K., Grajkowski, A., Phillips, L.R., and Beaucage, S.L. 2001. The 4-oxopentyl group, as a labile phos-phate/ thiophosphate protecting group for synthetic oligodeoxyribonucleotides. Tetrahedron Lett. 42:5635-5639.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 5635-5639
    • Wilk, A.1    Chmielewski, M.K.2    Grajkowski, A.3    Phillips, L.R.4    Beaucage, S.L.5
  • 25
    • 0037031670 scopus 로고    scopus 로고
    • The 3-[(N-tert-butyl)carboxamido]-1-propyl group as an attractive phosphate/thiophosphate protecting group for solid-phase oligodeoxyribonu-cleotide synthesis
    • Wilk, A., Chmielewski, M.K., Grajkowski, A., Phillips, L.R., and Beaucage, S.L. 2002. The 3-[(N-tert-butyl)carboxamido]-1-propyl group as an attractive phosphate/thiophosphate protecting group for solid-phase oligodeoxyribonu-cleotide synthesis. J. Org. Chem. 67:6430-6438.
    • (2002) J. Org. Chem. , vol.67 , pp. 6430-6438
    • Wilk, A.1    Chmielewski, M.K.2    Grajkowski, A.3    Phillips, L.R.4    Beaucage, S.L.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.