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Volumn 39, Issue 3, 2011, Pages 1165-1175

Photosensitized [2 + 2] cycloaddition of N-acetylated cytosine affords stereoselective formation of cyclobutane pyrimidine dimer

Author keywords

[No Author keywords available]

Indexed keywords

CYTIDINE DERIVATIVE; CYTOSINE; DEOXYCYTIDINE; DNA DIRECTED DNA POLYMERASE ETA; OLIGONUCLEOTIDE; PYRIMIDINE DIMER; THYMIDINE DERIVATIVE; THYMIDYLYL (3'-5') THYMIDINE; UNCLASSIFIED DRUG;

EID: 79951566687     PISSN: 03051048     EISSN: 13624962     Source Type: Journal    
DOI: 10.1093/nar/gkq855     Document Type: Article
Times cited : (8)

References (44)
  • 1
    • 0001096447 scopus 로고
    • High-pressure-promoted [2+2] cycloadditions of imines with electron-rich alkenes A simple route to azetidines and b-amino carbonyl compounds
    • Aben, R.W.M., Smit, R. and Scheeren, J.W. (1987) High-pressure-promoted [2+2] cycloadditions of imines with electron-rich alkenes. A simple route to azetidines and b-amino carbonyl compounds. J. Org. Chem., 52, 365-370.
    • (1987) J. Org. Chem. , vol.52 , pp. 365-370
    • Aben, R.W.M.1    Smit, R.2    Scheeren, J.W.3
  • 3
    • 1442275487 scopus 로고    scopus 로고
    • A Photochemical Approach to the Galanthan Ring System
    • DOI 10.1021/jo0356560
    • Minter, D.E. and Winslow, C.D. (2004) A photochemical approach to the galanthan ring system. J. Org. Chem., 69, 1603-1606. (Pubitemid 38280407)
    • (2004) Journal of Organic Chemistry , vol.69 , Issue.5 , pp. 1603-1606
    • Minter, D.E.1    Winslow, C.D.2
  • 5
    • 69449088022 scopus 로고    scopus 로고
    • Harvesting the strain installed by a Paterno-Buchi step in a synthetically useful way: High-yielding photoprotolytic oxametathesis in polycyclic systems
    • Valiulin, R.A. and Kutateladze, A.G. (2009) Harvesting the strain installed by a Paterno-Buchi step in a synthetically useful way: high-yielding photoprotolytic oxametathesis in polycyclic systems. Org. Lett., 11, 3886-3889.
    • (2009) Org. Lett. , vol.11 , pp. 3886-3889
    • Valiulin, R.A.1    Kutateladze, A.G.2
  • 6
    • 70349625606 scopus 로고    scopus 로고
    • Pyrimidine dimers: UV-induced DNA damage
    • Herdewijn, P. (ed.) Wiley-VCH, Weinheim
    • Iwai, S. (2008) Pyrimidine dimers: UV-induced DNA damage. In Herdewijn, P. (ed.), Modified Nucleosides in Biochemistry, Biotechnology and Medicine. Wiley-VCH, Weinheim, pp. 97-131.
    • (2008) Modified Nucleosides in Biochemistry, Biotechnology and Medicine , pp. 97-131
    • Iwai, S.1
  • 8
    • 0014427572 scopus 로고
    • Trans-syn thymine dimers in ultraviolet-irradiated denatured DNA: Identification and photoreactivability
    • Ben-Hur, E. and Ben-Ishai, R. (1968) Trans-syn thymine dimers in ultraviolet-irradiated denatured DNA: identification and photoreactivability. Biochim. Biophys. Acta, 166, 9-15.
    • (1968) Biochim. Biophys. Acta , vol.166 , pp. 9-15
    • Ben-Hur, E.1    Ben-Ishai, R.2
  • 9
    • 0034051701 scopus 로고    scopus 로고
    • Electrospray-mass spectrometry characterization and measurement of far-UV-induced thymine photoproducts
    • DOI 10.1016/S1011-1344(00)00009-9, PII S1011134400000099
    • Douki, T., Court, M. and Cadet, J. (2000) Electrospray-mass spectrometry characterization and measurement of far-UV-induced thymine photoproducts. J. Photochem. Photobiol. B, 54, 145-154. (Pubitemid 30224082)
    • (2000) Journal of Photochemistry and Photobiology B: Biology , vol.54 , Issue.2-3 , pp. 145-154
    • Douki, T.1    Court, M.2    Cadet, J.3
  • 10
    • 29644444403 scopus 로고    scopus 로고
    • Effect of denaturation on the photochemistry of pyrimidine bases in isolated DNA
    • DOI 10.1016/j.jphotobiol.2005.08.009, PII S1011134405001715
    • Douki, T. (2006) Effect of denaturation on the photochemistry of pyrimidine bases in isolated DNA. J. Photochem. Photobiol. B, 82, 45-52. (Pubitemid 43019632)
    • (2006) Journal of Photochemistry and Photobiology B: Biology , vol.82 , Issue.1 , pp. 45-52
    • Douki, T.1
  • 11
    • 0034697177 scopus 로고    scopus 로고
    • Formation of the main UV-induced thymine dimeric lesions within isolated and cellular DNA as measured by high performance liquid chromatography-tandem mass spectrometry
    • DOI 10.1074/jbc.275.16.11678
    • Douki, T., Court, M., Sauvaigo, S., Odin, F. and Cadet, J. (2000) Formation of the main UV-induced thymine dimeric lesions within isolated and cellular DNA as measured by high performance liquid chromatography-tandem mass spectrometry. J. Biol. Chem., 275, 11678-11685. (Pubitemid 30237729)
    • (2000) Journal of Biological Chemistry , vol.275 , Issue.16 , pp. 11678-11685
    • Douki, T.1    Court, M.2    Sauvaigo, S.3    Odin, F.4    Cadet, J.5
  • 12
    • 0027282986 scopus 로고
    • DNA photolyase repairs the trans-syn cyclobutane thymine dimer
    • Kim, S.-T., Malhotra, K., Smith, C.A., Taylor, J.-S. and Sancar, A. (1993) DNA photolyase repairs the trans-syn cyclobutane thymine dimer. Biochemistry, 32, 7065-7068. (Pubitemid 23223108)
    • (1993) Biochemistry , vol.32 , Issue.28 , pp. 7065-7068
    • Kim, S.-T.1    Malhotra, K.2    Smith, C.A.3    Taylor, J.-S.4    Sancar, A.5
  • 13
    • 0027241990 scopus 로고
    • Preparation and characterization of a set of deoxyoligonucleotide 49-mers containing site-specific cis-syn, trans-syn-I, (6-4), and Dewar photoproducts of thymidylyl(3' → 5')-thymidine
    • 0)-thymidine. J. Biol. Chem., 268, 11143-11151. (Pubitemid 23162304)
    • (1993) Journal of Biological Chemistry , vol.268 , Issue.15 , pp. 11143-11151
    • Smith, C.A.1    Taylor, J.-S.2
  • 14
    • 0027445650 scopus 로고
    • Comparative analysis of binding of human damaged DNA-binding protein (XPE) and Escherichia coli damage recognition protein (UvrA) to the major ultraviolet photoproducts: T[c,s]T, T[t,s]T, T[6-4]T, and T[Dewar]T
    • Reardon, J.T., Nichols, A.F., Keeney, S., Smith, C.A., Taylor, J.-S., Linn, S. and Sancar, A. (1993) Comparative analysis of binding of human damaged DNA-binding protein (XPE) and Escherichia coli damage recognition protein (UvrA) to the major ultraviolet photoproducts: T[c, s]T, T[t, s]T, T[6-4]T, and T[Dewar]T. J. Biol. Chem., 268, 21301-21308. (Pubitemid 23292321)
    • (1993) Journal of Biological Chemistry , vol.268 , Issue.28 , pp. 21301-21308
    • Reardon, J.T.1    Nichols, A.F.2    Keeney, S.3    Smith, C.A.4    Taylor, J.-S.5    Linn, S.6    Sancar, A.7
  • 15
    • 50249174575 scopus 로고    scopus 로고
    • Structure determination of an interstrand-type cis-anti cyclobutane thymine dimer produced in high yield by UVB light in an oligodeoxynucleotide at acidic pH
    • Su, D.G.T., Kao, J.L.-F., Gross, M.L. and Taylor, J.-S. (2008) Structure determination of an interstrand-type cis-anti cyclobutane thymine dimer produced in high yield by UVB light in an oligodeoxynucleotide at acidic pH. J. Am. Chem. Soc., 130, 11328-11337.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 11328-11337
    • Su, D.G.T.1    Kao, J.L.-F.2    Gross, M.L.3    Taylor, J.-S.4
  • 16
    • 69149089536 scopus 로고    scopus 로고
    • Photocrosslinking of human telomeric G-quadruplex loops by anti cyclobutane thymine dimer formation
    • Su, D.G.T., Fang, H., Gross, M.L. and Taylor, J.-S. (2009) Photocrosslinking of human telomeric G-quadruplex loops by anti cyclobutane thymine dimer formation. Proc. Natl Acad. Sci. USA, 106, 12861-12866.
    • (2009) Proc. Natl Acad. Sci. USA , vol.106 , pp. 12861-12866
    • Su, D.G.T.1    Fang, H.2    Gross, M.L.3    Taylor, J.-S.4
  • 18
    • 0027604555 scopus 로고
    • Quantum yields and secondary photoreactions of the photoproducts of dTpdT dTpdC and dTpdU
    • Lemaire, D.G.E. and Ruzsicska, B.P. (1993) Quantum yields and secondary photoreactions of the photoproducts of dTpdT, dTpdC and dTpdU. Photochem. Photobiol., 57, 755-769.
    • (1993) Photochem. Photobiol. , vol.57 , pp. 755-769
    • Lemaire, D.G.E.1    Ruzsicska, B.P.2
  • 19
  • 20
    • 0028810970 scopus 로고
    • Deamination of cytosine-containing pyrimidine photodimers in UV-irradiated DNA Significance for UV light mutagenesis
    • Barak, Y., Cohen-Fix, O. and Livneh, Z. (1995) Deamination of cytosine-containing pyrimidine photodimers in UV-irradiated DNA. Significance for UV light mutagenesis. J. Biol. Chem., 270, 24174-24179.
    • (1995) J. Biol. Chem. , vol.270 , pp. 24174-24179
    • Barak, Y.1    Cohen-Fix, O.2    Livneh, Z.3
  • 21
    • 0029758924 scopus 로고    scopus 로고
    • Accelerated deamination of cytosine residues in UV-induced cyclobutane pyrimidine dimers leads to CC→TT transitions
    • DOI 10.1021/bi960001x
    • Peng, W. and Shaw, B.R. (1996) Accelerated deamination of cytosine residues in UV-induced cyclobutane pyrimidine dimers leads to CC!TT transitions. Biochemistry, 35, 10172-10181. (Pubitemid 26269935)
    • (1996) Biochemistry , vol.35 , Issue.31 , pp. 10172-10181
    • Peng, W.1    Shaw, B.R.2
  • 22
    • 0032573433 scopus 로고    scopus 로고
    • Sequence and time-dependent deamination of cytosine bases in UVB-induced cyclobutane pyrimidine dimers in vivo
    • DOI 10.1006/jmbi.1998.2176
    • Tu, Y., Dammann, R. and Pfeifer, G.P. (1998) Sequence and time-dependent deamination of cytosine bases in UVB-induced cyclobutane pyrimidine dimers in vivo. J. Mol. Biol., 284, 297-311. (Pubitemid 28542455)
    • (1998) Journal of Molecular Biology , vol.284 , Issue.2 , pp. 297-311
    • Tu, Y.1    Dammann, R.2    Pfeifer, G.P.3
  • 23
    • 3042673439 scopus 로고    scopus 로고
    • Chemical synthesis and translesion replication of a cis-syn cyclobutane thymine-uracil dimer
    • DOI 10.1093/nar/gkh342
    • Takasawa, K., Masutani, C., Hanaoka, F. and Iwai, S. (2004) Chemical synthesis and translesion replication of a cis-syn cyclobutane thymine-uracil dimer. Nucleic Acids Res., 32, 1738-1745. (Pubitemid 38832718)
    • (2004) Nucleic Acids Research , vol.32 , Issue.5 , pp. 1738-1745
    • Takasawa, K.1    Masutani, C.2    Hanaoka, F.3    Iwai, S.4
  • 24
    • 0027416683 scopus 로고
    • Kinetic analysis of the deamination reactions of cyclobutane dimers of thymidylyl-3',5'-2'-deoxycytidine and 2'-deoxycytidylyl-3',5'-thymidine
    • 0-thymidine. Biochemistry, 32, 2525-2533. (Pubitemid 23090638)
    • (1993) Biochemistry , vol.32 , Issue.10 , pp. 2525-2533
    • Lemaire, D.G.E.1    Ruzsicska, B.P.2
  • 25
    • 0026726159 scopus 로고
    • 0)-thymidine: Isolation and characterization of the main photoproducts
    • 0)-thymidine: isolation and characterization of the main photoproducts. J. Photochem. Photobiol. B, 15, 199-213.
    • (1992) J. Photochem. Photobiol. B , vol.15 , pp. 199-213
    • Douki, T.1    Cadet, J.2
  • 27
    • 0028053714 scopus 로고
    • Formation of cyclobutane dimers and (6-4) photoproducts upon far-UV photolysis of 5-methylcytosine-containing dinucleoside monophosphates
    • DOI 10.1021/bi00205a033
    • Douki, T. and Cadet, J. (1994) Formation of cyclobutane dimers and (6-4) photoproducts upon far-UV photolysis of 5-methylcytosine-containing dinucleotide monophosphates. Biochemistry, 33, 11942-11950. (Pubitemid 24328005)
    • (1994) Biochemistry , vol.33 , Issue.39 , pp. 11942-11950
    • Douki, T.1    Cadet, J.2
  • 28
    • 33746588178 scopus 로고    scopus 로고
    • DNA synthesis past a 5-methylc-containing cis-syn-cyclobutane pyrimidine dimer by yeast Pol η is highly nonmutagenic
    • DOI 10.1021/bi0602009
    • Vu, B., Cannistraro, V.J., Sun, L. and Taylor, J.-S. (2006) DNA synthesis past a 5-methylC-containing cis-syn-cyclobutane pyrimidine dimer by yeast pol Z is highly nonmutagenic. Biochemistry, 45, 9327-9335. (Pubitemid 44156396)
    • (2006) Biochemistry , vol.45 , Issue.30 , pp. 9327-9335
    • Vu, B.1    Cannistraro, V.J.2    Sun, L.3    Taylor, J.S.4
  • 29
    • 0019802611 scopus 로고
    • Synthesis of 4-triazolopyrimidinone nucleotide and its application in synthesis of 5-methylcytosine-containing oligodeoxyribonucleotides
    • Sung, W.L. (1981) Synthesis of 4-triazolopyrimidinone nucleotide and its application in synthesis of 5-methylcytosine-containing oligodeoxyribonucleotides. Nucleic Acids Res., 9, 6139-6151. (Pubitemid 12133117)
    • (1981) Nucleic Acids Research , vol.9 , Issue.22 , pp. 6139-6151
    • Sung, W.L.1
  • 30
    • 0029843242 scopus 로고    scopus 로고
    • Benzimidazolium triflate as an efficient promoter for nucleotide synthesis via the phosphoramidite method
    • DOI 10.1021/jo961569e, PII S0022326396015691
    • Hayakawa, Y., Kataoka, M. and Noyori, R. (1996) Benzimidazolium triflate as an efficient promoter for nucleotide synthesis via the phosphoramidite method. J. Org. Chem., 61, 7996-7997. (Pubitemid 26400918)
    • (1996) Journal of Organic Chemistry , vol.61 , Issue.23 , pp. 7996-7997
    • Hayakawa, Y.1    Kataoka, M.2    Noyori, R.3
  • 31
    • 0032501381 scopus 로고    scopus 로고
    • Facile synthesis of oligodeoxyribonucleotides via the phosphoramidite method without nucleoside base protection
    • DOI 10.1021/ja973731g
    • Hayakawa, Y. and Kataoka, M. (1998) Facile synthesis of oligodeoxyribonucleotides via the phosphoramidite method without nucleoside base protection. J. Am. Chem. Soc., 120, 12395-12401. (Pubitemid 29003594)
    • (1998) Journal of the American Chemical Society , vol.120 , Issue.48 , pp. 12395-12401
    • Hayakawa, Y.1    Kataoka, M.2
  • 32
    • 0037999871 scopus 로고    scopus 로고
    • Proton-block strategy for the synthesis of oligodeoxynucleotides without base protection, capping reaction, and P-N bond cleavage reaction
    • DOI 10.1021/jo034204k
    • Sekine, M., Ohkubo, A. and Seio, K. (2003) Proton-block strategy for the synthesis of oligodeoxynucleotides without base protection, capping reaction, and P-N bond cleavage reaction. J. Org. Chem., 68, 5478-5492. (Pubitemid 36830503)
    • (2003) Journal of Organic Chemistry , vol.68 , Issue.14 , pp. 5478-5492
    • Sekine, M.1    Ohkubo, A.2    Seio, K.3
  • 33
    • 0024283265 scopus 로고
    • Synthesis of a trans-syn thymine dimer building block Solid phase synthesis of CGTAT [t, s] TATGC
    • Taylor, J.-S. and Brockie, I.R. (1988) Synthesis of a trans-syn thymine dimer building block. Solid phase synthesis of CGTAT [t, s]TATGC. Nucleic Acids Res., 16, 5123-5136.
    • (1988) Nucleic Acids Res. , vol.16 , pp. 5123-5136
    • Taylor, J.-S.1    Brockie, I.R.2
  • 34
    • 0025667322 scopus 로고
    • Synthesis and characterization of a substrate for T4 endonuclease V containing a phosphorodithioate linkage at the thymine dimer site
    • Murata, T., Iwai, S. and Ohtsuka, E. (1990) Synthesis and characterization of a substrate for T4 endonuclease V containing a phosphorodithioate linkage at the thymine dimer site. Nucleic Acids Res., 18, 7279-7286. (Pubitemid 120006028)
    • (1990) Nucleic Acids Research , vol.18 , Issue.24 , pp. 7279-7286
    • Murata, T.1    Iwai, S.2    Ohtsuka, E.3
  • 35
    • 0032556210 scopus 로고    scopus 로고
    • Studies on the chemical synthesis of oligonucleotides containing the (6- 4) photoproduct of thymine-cytosine and its repair by (6-4) photolyase
    • DOI 10.1021/ja982004y
    • Mizukoshi, T., Hitomi, K., Todo, T. and Iwai, S. (1998) Studies on the chemical synthesis of oligonucleotides containing the (6-4) photoproduct of thymine-cytosine and its repair by (6-4) photolyase. J. Am. Chem. Soc., 120, 10634-10642. (Pubitemid 28498807)
    • (1998) Journal of the American Chemical Society , vol.120 , Issue.41 , pp. 10634-10642
    • Mizukoshi, T.1    Hitomi, K.2    Todo, T.3    Iwai, S.4
  • 36
    • 0344021084 scopus 로고
    • Kinetics and mechanism of the deamination of 1-methyl-5 6-dihydrocytosine
    • Slae, S. and Shapiro, R. (1978) Kinetics and mechanism of the deamination of 1-methyl-5, 6-dihydrocytosine. J. Org. Chem., 43, 1721-1726.
    • (1978) J. Org. Chem. , vol.43 , pp. 1721-1726
    • Slae, S.1    Shapiro, R.2
  • 37
    • 0026093232 scopus 로고
    • Unraveling the origin of the major mutation induced by ultraviolet light the C!T transition at dTpdC sites. A DNA synthesis building block for the cis-syn cyclobutane dimer of dTpdU
    • Taylor, J.-S. and Nadji, S. (1991) Unraveling the origin of the major mutation induced by ultraviolet light, the C!T transition at dTpdC sites. A DNA synthesis building block for the cis-syn cyclobutane dimer of dTpdU. Tetrahedron, 47, 2579-2590.
    • (1991) Tetrahedron , vol.47 , pp. 2579-2590
    • Taylor, J.-S.1    Nadji, S.2
  • 39
    • 0031860433 scopus 로고    scopus 로고
    • Synthesis, crystal structure, and enzymatic evaluation of a DNA-photolesion isostere
    • DOI 10.1002/(SICI)1521-3765(19980416)4:4<642::AID-CHEM642>3.0.CO;2- K
    • Butenandt, J., Eker, A.P.M. and Carell, T. (1998) Synthesis, crystal structure, and enzymatic evaluation of a DNA-photolesion isostere. Chem. Eur. J., 4, 642-654. (Pubitemid 28286168)
    • (1998) Chemistry - A European Journal , vol.4 , Issue.4 , pp. 642-654
    • Butenandt, J.1    Eker, A.P.M.2    Carell, T.3
  • 40
    • 10044280323 scopus 로고    scopus 로고
    • Crystal structure of a photolyase bound to a CPD-like DNA lesion after in situ repair
    • DOI 10.1126/science.1101598
    • Mees, A., Klar, T., Gnau, P., Hennecke, U., Eker, A.P.M., Carell, T. and Essen, L.-O. (2004) Crystal structure of a photolyase bound to a CPD-like DNA lesion after in situ repair. Science, 306, 1789-1793. (Pubitemid 39601399)
    • (2004) Science , vol.306 , Issue.5702 , pp. 1789-1793
    • Mees, A.1    Klar, T.2    Gnau, P.3    Hennecke, U.4    Eker, A.P.M.5    Carell, T.6    Essen, L.-O.7
  • 41
    • 0037021344 scopus 로고    scopus 로고
    • Cleavable substrate containing molecular beacons for the quantification of DNA-photolyase activity
    • DOI 10.1002/1439-7633(20021104)3:11<1053::AID-CBIC1053>3.0.CO;2-#
    • Kundu, L.M., Burgdorf, L.T., Kleiner, O., Batschauer, A. and Carell, T. (2002) Cleavable substrate containing molecular beacons for the quantification of DNA-photolyase activity. ChemBioChem, 3, 1053-1060. (Pubitemid 36008034)
    • (2002) ChemBioChem , vol.3 , Issue.11 , pp. 1053-1060
    • Kundu, L.M.1    Burgdorf, L.T.2    Kleiner, O.3    Batschauer, A.4    Carell, T.5
  • 42
    • 0036259993 scopus 로고    scopus 로고
    • Weak distance dependence of excess electron transfer in DNA
    • DOI 10.1002/1521-3773(20020517)41:10<1763::AID-ANIE1763>3.0.CO;2-M
    • Behrens, C., Burgdorf, L.T., Schwogler, A. and Carell, T. (2002) Weak distance dependence of excess electron transfer in DNA. Angew. Chem. Int. Ed., 41, 1763-1766. (Pubitemid 34568422)
    • (2002) Angewandte Chemie - International Edition , vol.41 , Issue.10 , pp. 1763-1766
    • Behrens, C.1    Burgdorf, L.T.2    Schwogler, A.3    Carell, T.4
  • 44
    • 0034660259 scopus 로고    scopus 로고
    • Mechanisms of accurate translesion synthesis by human DNA polymerase η
    • Masutani, C., Kusumoto, R., Iwai, S. and Hanaoka, F. (2000) Mechanisms of accurate translesion synthesis by human DNA polymerase Z. EMBO J., 19, 3100-3109. (Pubitemid 30386780)
    • (2000) EMBO Journal , vol.19 , Issue.12 , pp. 3100-3109
    • Masutani, C.1    Kusumoto, R.2    Iwai, S.3    Hanaoka, F.4


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