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From an etiological point of view, 2,6-diaminopurine is not to be considered an unnaturally complex nucleobase; it can assemble from the same type of elementary building blocks as guanine can.
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7
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16
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0442267508
-
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note
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Carried out by Raj K. Chadha, TSRI. Crystallographic data for the structure has been deposited with the Cambridge Crystallographic Data Center as deposition No. CCDC 175169. Copies of the data can be obtained, free of charge, on application to the CCDC, 12 Union Road, Cambridge, CB12 1EZ UK (fax + 44 (1233) 3360333; e-mail deposit@ccdc.cam.ac.uk).
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17
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0347755890
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Zorbach, W. W., Tipson, R. S., Eds. Interscience Publishers: New York
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Thomas, H. J.; Johnson, J. A.; Fitzgibbon, W. E.; Clayton, S. J.; Baker, B. R.; Synthetic Proceedures in Nucleic acids Chemistry; Zorbach, W. W., Tipson, R. S., Eds. Interscience Publishers: New York, 1968; Vol. 1, p 249.
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18
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0030846261
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13C NMR and mass spectral data after purification by column chromatography on silica gel. A full experimental account will be published in Helv. Chim. Acta. Oligonucleotides were synthesized on an Expedite 8909 Nucleic Acid Synthesizer (Perseptive Biosystems), purified by HPLC (ion exchange column SAX 1000-8 (Macherey-Nagel)) up to a minimal purity of 95% and shown to have the expected molecular mass by MALDI-TOF MS (Supporting Information). Ligand sequences containing a 2′-phosphate group were made using a DMTO-ethylsulfonyl derivatized-CPG solid support (see Bolli, M.; Micura, R.; Pitsch, S.; Eschenmoser, A. Helv. Chim. Acta 1997, 80, 1901; formula in footnote 5). Ligand sequences containing 3′-amino threofuranosyl adenine as the end group were synthesized using the required building block described in ref 3. RNA oligonucleotides were purchased from Xeragon Inc. and DNA(A,T) oligonucleotides from Operon Technologies Inc.
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Helv. Chim. Acta
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19
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0030846261
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13C NMR and mass spectral data after purification by column chromatography on silica gel. A full experimental account will be published in Helv. Chim. Acta. Oligonucleotides were synthesized on an Expedite 8909 Nucleic Acid Synthesizer (Perseptive Biosystems), purified by HPLC (ion exchange column SAX 1000-8 (Macherey-Nagel)) up to a minimal purity of 95% and shown to have the expected molecular mass by MALDI-TOF MS (Supporting Information). Ligand sequences containing a 2′-phosphate group were made using a DMTO-ethylsulfonyl derivatized-CPG solid support (see Bolli, M.; Micura, R.; Pitsch, S.; Eschenmoser, A. Helv. Chim. Acta 1997, 80, 1901; formula in footnote 5). Ligand sequences containing 3′-amino threofuranosyl adenine as the end group were synthesized using the required building block described in ref 3. RNA oligonucleotides were purchased from Xeragon Inc. and DNA(A,T) oligonucleotides from Operon Technologies Inc.
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0442264443
-
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note
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8).
-
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21
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0029954409
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Stability rise increments are expected to depend on sequences and are not expected to remain the same with increasing the number of (A → D) replacements. See: Sági, J.; Szakanyi, E.; Vorlícková, M.; Kypr. J. J. Biomol. Struct. Dyn. 1996, 13, 1035.
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24
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0019848046
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N-(3-Dimethyl(aminopropyl)-N′-ethylcarbodiimide hydrochloride (= EDC); see, e.g., Shabarova, Z. A.; Dolinnaya, N. G.; Drusta, V. L.; Melnikova, N. P.; Purmal, A. A. Nucleic Acids Res. 1981, 9, 5747.
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Hartel, C.; Göbel, M. W. Helv Chim. Acta 2000, 83, 2541. Kozlov, I.; Orgel, L. E. Helv. Chim. Acta 1999, 82, 1799. See also the ligation experiments in the p-RNA series: Bolli, M.; Micura, R.; Eschenmoser, A. Chem. Biol. 1997, 4, 309.
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Schmidt, J. G.; Nielsen, P. E.; Orgel, L. E. Nucl. Acids Res. 1997, 25, 4797 and literature cited therein. Kozlov, I. A.; De Bouevere, B.; Aerschot, A. v.; Herdewijn, P.; Orgel, L. E. J. Am. Chem. Soc. 1999, 121, 5856. Kozlov, I. A.; Zelinski, M.; Allart, B.; Kerremans, L.; Aerschot, A. v.; Busson, R.; Herdewijn, P.; Orgel, L. E. Chem. Eur. J. 2000, 6, 151. Koppitz, M.; Nielsen, P. E.; Orgel, L. E. J. Am. Chem. Soc. 1998, 120, 4563.
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34
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0033962218
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Schmidt, J. G.; Nielsen, P. E.; Orgel, L. E. Nucl. Acids Res. 1997, 25, 4797 and literature cited therein. Kozlov, I. A.; De Bouevere, B.; Aerschot, A. v.; Herdewijn, P.; Orgel, L. E. J. Am. Chem. Soc. 1999, 121, 5856. Kozlov, I. A.; Zelinski, M.; Allart, B.; Kerremans, L.; Aerschot, A. v.; Busson, R.; Herdewijn, P.; Orgel, L. E. Chem. Eur. J. 2000, 6, 151. Koppitz, M.; Nielsen, P. E.; Orgel, L. E. J. Am. Chem. Soc. 1998, 120, 4563.
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35
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Schmidt, J. G.; Nielsen, P. E.; Orgel, L. E. Nucl. Acids Res. 1997, 25, 4797 and literature cited therein. Kozlov, I. A.; De Bouevere, B.; Aerschot, A. v.; Herdewijn, P.; Orgel, L. E. J. Am. Chem. Soc. 1999, 121, 5856. Kozlov, I. A.; Zelinski, M.; Allart, B.; Kerremans, L.; Aerschot, A. v.; Busson, R.; Herdewijn, P.; Orgel, L. E. Chem. Eur. J. 2000, 6, 151. Koppitz, M.; Nielsen, P. E.; Orgel, L. E. J. Am. Chem. Soc. 1998, 120, 4563.
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36
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0442264440
-
-
note
-
Slow ligation rates allow side reactions (due to large excess of the carbodiimide activation agent) to hamper product formation.
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-
-
-
37
-
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0031215115
-
-
For recent studies on the fidelity of template-controlled ligations see, for examle, Kenneth, J.; Ellington, A. D. Chem. Biol. 1997, 4, 595. Bolli, M.; Micura, R.; Pitsch, S.; Eschenmoser, A. Helv. Chim. Acta 1997, 80, 1901. Mattes, A.; Seitz, O. Chem. Commun. 2001, 2050.
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For recent studies on the fidelity of template-controlled ligations see, for examle, Kenneth, J.; Ellington, A. D. Chem. Biol. 1997, 4, 595. Bolli, M.; Micura, R.; Pitsch, S.; Eschenmoser, A. Helv. Chim. Acta 1997, 80, 1901. Mattes, A.; Seitz, O. Chem. Commun. 2001, 2050.
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39
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0035929795
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For recent studies on the fidelity of template-controlled ligations see, for examle, Kenneth, J.; Ellington, A. D. Chem. Biol. 1997, 4, 595. Bolli, M.; Micura, R.; Pitsch, S.; Eschenmoser, A. Helv. Chim. Acta 1997, 80, 1901. Mattes, A.; Seitz, O. Chem. Commun. 2001, 2050.
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Mattes, A.1
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40
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For the inefficiency of chemical ligation of RNA ligands on DNA templates, see the following: Dolinnaya, N. G.; Sokolova, N. I.; Ashirbekova, D. T.; Shabarova, Z. A. Nucleic Acids Res. 1991, 19, 3067.
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-
41
-
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0442264441
-
-
note
-
m values (c ≈ 5 μM, 1 M NaCl) of template strands: TNA-(A,T), <5 °C; TNA(D,T), 30 °C.
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-
-
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