메뉴 건너뛰기




Volumn 45, Issue 12, 2012, Pages 2055-2065

Natural versus artificial creation of base pairs in DNA: Origin of nucleobases from the perspectives of unnatural base pair studies

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE; CYTOSINE; DNA; DNA DIRECTED DNA POLYMERASE; GUANOSINE; ISOCARBOSTYRIL; ISOQUINOLINE DERIVATIVE; NUCLEOTIDE; THYMIDINE;

EID: 84865283348     PISSN: 00014842     EISSN: 15204898     Source Type: Journal    
DOI: 10.1021/ar200257x     Document Type: Review
Times cited : (130)

References (66)
  • 1
    • 0003075565 scopus 로고
    • Problems of evolution and biochemical information transfer
    • In; Kasha, M. P. B. Academic Press
    • Rich, A. Problems of evolution and biochemical information transfer. In Horizons in Biochemistry; Kasha, M. P. B., Ed.; Academic Press: 1962; pp 103-126.
    • (1962) Horizons in Biochemistry , pp. 103-126
    • Rich, A.1
  • 2
    • 0345304414 scopus 로고    scopus 로고
    • Why are there four letters in the genetic alphabet?
    • Szathmary, E. Why are there four letters in the genetic alphabet? Nat. Rev. Genet. 2003, 4, 995-1001
    • (2003) Nat. Rev. Genet. , vol.4 , pp. 995-1001
    • Szathmary, E.1
  • 4
    • 0001187396 scopus 로고
    • Mechanism of synthesis of adenine from hydrogen cyanide under possible primitive earth conditions
    • Oro, J. Mechanism of synthesis of adenine from hydrogen cyanide under possible primitive earth conditions Nature 1961, 191, 1193-1194
    • (1961) Nature , vol.191 , pp. 1193-1194
    • Oro, J.1
  • 5
    • 0014433426 scopus 로고
    • Studies in prebiotic synthesis. IV. Conversion of 4-aminoimidazole-5- carbonitrile derivatives to purines
    • Sanchez, R. A.; Ferris, J. P.; Orgel, L. E. Studies in prebiotic synthesis. IV. Conversion of 4-aminoimidazole-5-carbonitrile derivatives to purines J. Mol. Biol. 1968, 38, 121-128
    • (1968) J. Mol. Biol. , vol.38 , pp. 121-128
    • Sanchez, R.A.1    Ferris, J.P.2    Orgel, L.E.3
  • 6
    • 66149108671 scopus 로고    scopus 로고
    • Synthesis of activated pyrimidine ribonucleotides in prebiotically plausible conditions
    • Powner, M. W.; Gerland, B.; Sutherland, J. D. Synthesis of activated pyrimidine ribonucleotides in prebiotically plausible conditions Nature 2009, 459, 239-242
    • (2009) Nature , vol.459 , pp. 239-242
    • Powner, M.W.1    Gerland, B.2    Sutherland, J.D.3
  • 7
    • 0037180804 scopus 로고    scopus 로고
    • A ribozyme composed of only two different nucleotides
    • Reader, J. S.; Joyce, G. F. A ribozyme composed of only two different nucleotides Nature 2002, 420, 841-844
    • (2002) Nature , vol.420 , pp. 841-844
    • Reader, J.S.1    Joyce, G.F.2
  • 8
    • 6944225455 scopus 로고    scopus 로고
    • Understanding nucleic acids using synthetic chemistry
    • Benner, S. A. Understanding nucleic acids using synthetic chemistry Acc. Chem. Res. 2004, 37, 784-797
    • (2004) Acc. Chem. Res. , vol.37 , pp. 784-797
    • Benner, S.A.1
  • 9
    • 0344851941 scopus 로고    scopus 로고
    • Beyond A, C, G and T: Augmenting nature's alphabet
    • Henry, A. A.; Romesberg, F. E. Beyond A, C, G and T: augmenting nature's alphabet Curr. Opin. Chem. Biol. 2003, 7, 727-733
    • (2003) Curr. Opin. Chem. Biol. , vol.7 , pp. 727-733
    • Henry, A.A.1    Romesberg, F.E.2
  • 10
    • 62649161943 scopus 로고    scopus 로고
    • Redesigning the architecture of the base pair: Toward biochemical and biological function of new genetic sets
    • Krueger, A. T.; Kool, E. T. Redesigning the architecture of the base pair: toward biochemical and biological function of new genetic sets Chem. Biol. 2009, 16, 242-248
    • (2009) Chem. Biol. , vol.16 , pp. 242-248
    • Krueger, A.T.1    Kool, E.T.2
  • 11
    • 33846393737 scopus 로고    scopus 로고
    • Unnatural base pair systems for DNA/RNA-based biotechnology
    • Hirao, I. Unnatural base pair systems for DNA/RNA-based biotechnology Curr. Opin. Chem. Biol. 2006, 10, 622-627
    • (2006) Curr. Opin. Chem. Biol. , vol.10 , pp. 622-627
    • Hirao, I.1
  • 12
    • 79953888771 scopus 로고    scopus 로고
    • Unnatural base pair systems for sensing and diagnostic applications
    • Kimoto, M.; Cox, R. S., 3rd; Hirao, I. Unnatural base pair systems for sensing and diagnostic applications Expert Rev. Mol. Diagn. 2011, 11, 321-331
    • (2011) Expert Rev. Mol. Diagn. , vol.11 , pp. 321-331
    • Kimoto, M.1    Cox III, R.S.2    Hirao, I.3
  • 13
    • 0024325247 scopus 로고
    • Enzymatic incorporation of a new base pair into DNA and RNA
    • Switzer, C.; Moroney, S. E.; Benner, S. A. Enzymatic incorporation of a new base pair into DNA and RNA J. Am. Chem. Soc. 1989, 111, 8322-8323
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 8322-8323
    • Switzer, C.1    Moroney, S.E.2    Benner, S.A.3
  • 14
    • 0024284583 scopus 로고
    • The 6-thioguanine/5-methyl-2-pyrimidinone base pair
    • Rappaport, H. P. The 6-thioguanine/5-methyl-2-pyrimidinone base pair Nucleic Acids Res. 1988, 16, 7253-7267
    • (1988) Nucleic Acids Res. , vol.16 , pp. 7253-7267
    • Rappaport, H.P.1
  • 15
    • 0025008851 scopus 로고
    • Enzymatic incorporation of a new base pair into DNA and RNA extends the genetic alphabet
    • Piccirilli, J. A.; Krauch, T.; Moroney, S. E.; Benner, S. A. Enzymatic incorporation of a new base pair into DNA and RNA extends the genetic alphabet Nature 1990, 343, 33-37
    • (1990) Nature , vol.343 , pp. 33-37
    • Piccirilli, J.A.1    Krauch, T.2    Moroney, S.E.3    Benner, S.A.4
  • 16
    • 0027492904 scopus 로고
    • Enzymatic recognition of the base pair between isocytidine and isoguanosine
    • Switzer, C. Y.; Moroney, S. E.; Benner, S. A. Enzymatic recognition of the base pair between isocytidine and isoguanosine Biochemistry 1993, 32, 10489-10496
    • (1993) Biochemistry , vol.32 , pp. 10489-10496
    • Switzer, C.Y.1    Moroney, S.E.2    Benner, S.A.3
  • 18
    • 80053068450 scopus 로고    scopus 로고
    • Amplification, mutation, and sequencing of a six-letter synthetic genetic system
    • Yang, Z.; Chen, F.; Alvarado, J. B.; Benner, S. A. Amplification, mutation, and sequencing of a six-letter synthetic genetic system J. Am. Chem. Soc. 2011, 133, 15105-15112
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 15105-15112
    • Yang, Z.1    Chen, F.2    Alvarado, J.B.3    Benner, S.A.4
  • 19
    • 0031792598 scopus 로고    scopus 로고
    • Efficient replication between non-hydrogen-bonded nucleoside shape analogs
    • Morales, J. C.; Kool, E. T. Efficient replication between non-hydrogen-bonded nucleoside shape analogs Nat. Struct. Biol. 1998, 5, 950-954
    • (1998) Nat. Struct. Biol. , vol.5 , pp. 950-954
    • Morales, J.C.1    Kool, E.T.2
  • 20
    • 0033572961 scopus 로고    scopus 로고
    • Efforts toward expansion of the genetic alphabet: DNA polymerase recognition of a highly stable, self-pairing hydrophobicbase
    • McMinn, D. L.; Ogawa, A. K.; Wu, Y.; Liu, J.; Schultz, P. G.; Romesberg, F. E. Efforts toward expansion of the genetic alphabet: DNA polymerase recognition of a highly stable, self-pairing hydrophobicbase J. Am. Chem. Soc. 1999, 121, 11585-11586
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 11585-11586
    • McMinn, D.L.1    Ogawa, A.K.2    Wu, Y.3    Liu, J.4    Schultz, P.G.5    Romesberg, F.E.6
  • 22
    • 78249251747 scopus 로고    scopus 로고
    • Solution structure, mechanism of replication, and optimization of an unnatural base pair
    • Malyshev, D. A.; Pfaff, D. A.; Ippoliti, S. I.; Hwang, G. T.; Dwyer, T. J.; Romesberg, F. E. Solution structure, mechanism of replication, and optimization of an unnatural base pair Chemistry 2010, 16, 12650-12659
    • (2010) Chemistry , vol.16 , pp. 12650-12659
    • Malyshev, D.A.1    Pfaff, D.A.2    Ippoliti, S.I.3    Hwang, G.T.4    Dwyer, T.J.5    Romesberg, F.E.6
  • 23
    • 59649091247 scopus 로고    scopus 로고
    • An unnatural base pair system for efficient PCR amplification and functionalization of DNA molecules
    • Kimoto, M.; Kawai, R.; Mitsui, T.; Yokoyama, S.; Hirao, I. An unnatural base pair system for efficient PCR amplification and functionalization of DNA molecules Nucleic Acids Res. 2009, 37, e14
    • (2009) Nucleic Acids Res. , vol.37 , pp. 14
    • Kimoto, M.1    Kawai, R.2    Mitsui, T.3    Yokoyama, S.4    Hirao, I.5
  • 26
    • 0037955524 scopus 로고    scopus 로고
    • An unnatural hydrophobic base pair with shape complementarity between pyrrole-2-carbaldehyde and 9-methylimidazo[(4,5)-b]pyridine
    • Mitsui, T.; Kitamura, A.; Kimoto, M.; To, T.; Sato, A.; Hirao, I.; Yokoyama, S. An unnatural hydrophobic base pair with shape complementarity between pyrrole-2-carbaldehyde and 9-methylimidazo[(4,5)-b]pyridine J. Am. Chem. Soc. 2003, 125, 5298-5307
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 5298-5307
    • Mitsui, T.1    Kitamura, A.2    Kimoto, M.3    To, T.4    Sato, A.5    Hirao, I.6    Yokoyama, S.7
  • 27
    • 33747762272 scopus 로고    scopus 로고
    • An unnatural hydrophobic base pair system: Site-specific incorporation of nucleotide analogs into DNA and RNA
    • Hirao, I.; Kimoto, M.; Mitsui, T.; Fujiwara, T.; Kawai, R.; Sato, A.; Harada, Y.; Yokoyama, S. An unnatural hydrophobic base pair system: site-specific incorporation of nucleotide analogs into DNA and RNA Nat. Methods 2006, 3, 729-735
    • (2006) Nat. Methods , vol.3 , pp. 729-735
    • Hirao, I.1    Kimoto, M.2    Mitsui, T.3    Fujiwara, T.4    Kawai, R.5    Sato, A.6    Harada, Y.7    Yokoyama, S.8
  • 28
    • 37849014324 scopus 로고    scopus 로고
    • An efficient unnatural base pair for PCR amplification
    • Hirao, I.; Mitsui, T.; Kimoto, M.; Yokoyama, S. An efficient unnatural base pair for PCR amplification J. Am. Chem. Soc. 2007, 129, 15549-15555
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 15549-15555
    • Hirao, I.1    Mitsui, T.2    Kimoto, M.3    Yokoyama, S.4
  • 30
    • 0033577360 scopus 로고    scopus 로고
    • Minor groove interactions between polymerase and DNA: More essential to replication than Watson-Crick hydrogen bonds?
    • Morales, J. C.; Kool, E. T. Minor groove interactions between polymerase and DNA: more essential to replication than Watson-Crick hydrogen bonds? J. Am. Chem. Soc. 1999, 121, 2323-2324
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 2323-2324
    • Morales, J.C.1    Kool, E.T.2
  • 31
    • 0031790169 scopus 로고    scopus 로고
    • Solution structure of a DNA duplex containing a replicable difluorotoluene-adenine pair
    • Guckian, K. M.; Krugh, T. R.; Kool, E. T. Solution structure of a DNA duplex containing a replicable difluorotoluene-adenine pair Nat. Struct. Biol. 1998, 5, 954-959
    • (1998) Nat. Struct. Biol. , vol.5 , pp. 954-959
    • Guckian, K.M.1    Krugh, T.R.2    Kool, E.T.3
  • 33
    • 77954306363 scopus 로고    scopus 로고
    • Site-specific fluorescent probing of RNA molecules by unnatural base-pair transcription for local structural conformation analysis
    • Hikida, Y.; Kimoto, M.; Yokoyama, S.; Hirao, I. Site-specific fluorescent probing of RNA molecules by unnatural base-pair transcription for local structural conformation analysis Nat. Protoc. 2010, 5, 1312-1323
    • (2010) Nat. Protoc. , vol.5 , pp. 1312-1323
    • Hikida, Y.1    Kimoto, M.2    Yokoyama, S.3    Hirao, I.4
  • 35
    • 0034639916 scopus 로고    scopus 로고
    • Efforts toward the expansion of the genetic alphabet: Information storage and replication with unnatural hydrophobic base pairs
    • Ogawa, A. K.; Wu, Y.; McMinn, D. L.; Liu, J.; Schultz, P. G.; Romesberg, F. E. Efforts toward the expansion of the genetic alphabet: Information storage and replication with unnatural hydrophobic base pairs J. Am. Chem. Soc. 2000, 122, 3274-3287
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 3274-3287
    • Ogawa, A.K.1    Wu, Y.2    McMinn, D.L.3    Liu, J.4    Schultz, P.G.5    Romesberg, F.E.6
  • 36
    • 0041082559 scopus 로고    scopus 로고
    • Efforts toward expansion of the genetic alphabet: Optimization of interbase hydrophobic interactions
    • Wu, Y.; Ogawa, A. K.; Berger, M.; McMinn, D. L.; Schultz, P. G.; Romesberg, F. E. Efforts toward expansion of the genetic alphabet: Optimization of interbase hydrophobic interactions J. Am. Chem. Soc. 2000, 122, 7621-7632
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 7621-7632
    • Wu, Y.1    Ogawa, A.K.2    Berger, M.3    McMinn, D.L.4    Schultz, P.G.5    Romesberg, F.E.6
  • 37
    • 0034644435 scopus 로고    scopus 로고
    • Rational design of an unnatural base pair with increased kinetic selectivity
    • Ogawa, A. K.; Wu, Y.; Berger, M.; Schultz, P. G.; Romesberg, F. E. Rational design of an unnatural base pair with increased kinetic selectivity J. Am. Chem. Soc. 2000, 122, 8803-8804
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 8803-8804
    • Ogawa, A.K.1    Wu, Y.2    Berger, M.3    Schultz, P.G.4    Romesberg, F.E.5
  • 38
    • 0034835786 scopus 로고    scopus 로고
    • Efforts toward expansion of the genetic alphabet: Replication of DNA with three base pairs
    • Tae, E. L.; Wu, Y.; Xia, G.; Schultz, P. G.; Romesberg, F. E. Efforts toward expansion of the genetic alphabet: replication of DNA with three base pairs J. Am. Chem. Soc. 2001, 123, 7439-7440
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 7439-7440
    • Tae, E.L.1    Wu, Y.2    Xia, G.3    Schultz, P.G.4    Romesberg, F.E.5
  • 39
    • 24744447201 scopus 로고    scopus 로고
    • Polymerase evolution: Efforts toward expansion of the genetic code
    • Leconte, A. M.; Chen, L.; Romesberg, F. E. Polymerase evolution: efforts toward expansion of the genetic code J. Am. Chem. Soc. 2005, 127, 12470-12471
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 12470-12471
    • Leconte, A.M.1    Chen, L.2    Romesberg, F.E.3
  • 40
    • 0037138607 scopus 로고    scopus 로고
    • Stability and selectivity of unnatural DNA with five-membered-ring nucleobase analogues
    • Berger, M.; Luzzi, S. D.; Henry, A. A.; Romesberg, F. E. Stability and selectivity of unnatural DNA with five-membered-ring nucleobase analogues J. Am. Chem. Soc. 2002, 124, 1222-1226
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 1222-1226
    • Berger, M.1    Luzzi, S.D.2    Henry, A.A.3    Romesberg, F.E.4
  • 41
    • 3042816106 scopus 로고    scopus 로고
    • Efforts to expand the genetic alphabet: Identification of a replicable unnatural DNA self-pair
    • Henry, A. A.; Olsen, A. G.; Matsuda, S.; Yu, C.; Geierstanger, B. H.; Romesberg, F. E. Efforts to expand the genetic alphabet: identification of a replicable unnatural DNA self-pair J. Am. Chem. Soc. 2004, 126, 6923-6931
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 6923-6931
    • Henry, A.A.1    Olsen, A.G.2    Matsuda, S.3    Yu, C.4    Geierstanger, B.H.5    Romesberg, F.E.6
  • 42
    • 33744818886 scopus 로고    scopus 로고
    • An efficiently extended class of unnatural base pairs
    • Leconte, A. M.; Matsuda, S.; Romesberg, F. E. An efficiently extended class of unnatural base pairs J. Am. Chem. Soc. 2006, 128, 6780-6781
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 6780-6781
    • Leconte, A.M.1    Matsuda, S.2    Romesberg, F.E.3
  • 43
    • 34247889952 scopus 로고    scopus 로고
    • Minor groove hydrogen bonds and the replication of unnatural base pairs
    • Matsuda, S.; Leconte, A. M.; Romesberg, F. E. Minor groove hydrogen bonds and the replication of unnatural base pairs J. Am. Chem. Soc. 2007, 129, 5551-5557
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 5551-5557
    • Matsuda, S.1    Leconte, A.M.2    Romesberg, F.E.3
  • 45
    • 39549087460 scopus 로고    scopus 로고
    • Discovery, characterization, and optimization of an unnatural base pair for expansion of the genetic alphabet
    • Leconte, A. M.; Hwang, G. T.; Matsuda, S.; Capek, P.; Hari, Y.; Romesberg, F. E. Discovery, characterization, and optimization of an unnatural base pair for expansion of the genetic alphabet J. Am. Chem. Soc. 2008, 130, 2336-2343
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 2336-2343
    • Leconte, A.M.1    Hwang, G.T.2    Matsuda, S.3    Capek, P.4    Hari, Y.5    Romesberg, F.E.6
  • 46
    • 67849129011 scopus 로고    scopus 로고
    • Optimization of an unnatural base pair toward natural-like replication
    • Seo, Y. J.; Hwang, G. T.; Ordoukhanian, P.; Romesberg, F. E. Optimization of an unnatural base pair toward natural-like replication J. Am. Chem. Soc. 2009, 131, 3246-3252
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 3246-3252
    • Seo, Y.J.1    Hwang, G.T.2    Ordoukhanian, P.3    Romesberg, F.E.4
  • 47
    • 67849087122 scopus 로고    scopus 로고
    • Transcription of an expanded genetic alphabet
    • Seo, Y. J.; Matsuda, S.; Romesberg, F. E. Transcription of an expanded genetic alphabet J. Am. Chem. Soc. 2009, 131, 5046-5047
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 5046-5047
    • Seo, Y.J.1    Matsuda, S.2    Romesberg, F.E.3
  • 48
    • 0026523058 scopus 로고
    • Ribosome-mediated incorporation of a non-standard amino acid into a peptide through expansion of the genetic code
    • Bain, J. D.; Switzer, C.; Chamberlin, A. R.; Benner, S. A. Ribosome-mediated incorporation of a non-standard amino acid into a peptide through expansion of the genetic code Nature 1992, 356, 537-539
    • (1992) Nature , vol.356 , pp. 537-539
    • Bain, J.D.1    Switzer, C.2    Chamberlin, A.R.3    Benner, S.A.4
  • 49
    • 0029045480 scopus 로고
    • Recognition by viral and cellular DNA polymerases of nucleosides bearing bases with nonstandard hydrogen bonding patterns
    • Horlacher, J.; Hottiger, M.; Podust, V. N.; Hubscher, U.; Benner, S. A. Recognition by viral and cellular DNA polymerases of nucleosides bearing bases with nonstandard hydrogen bonding patterns Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 6329-6333
    • (1995) Proc. Natl. Acad. Sci. U.S.A. , vol.92 , pp. 6329-6333
    • Horlacher, J.1    Hottiger, M.2    Podust, V.N.3    Hubscher, U.4    Benner, S.A.5
  • 50
    • 3242798107 scopus 로고    scopus 로고
    • Xanthine, xanthosine and its nucleotides: Solution structures of neutral and ionic forms, and relevance to substrate properties in various enzyme systems and metabolic pathways
    • Kulikowska, E.; Kierdaszuk, B.; Shugar, D. Xanthine, xanthosine and its nucleotides: solution structures of neutral and ionic forms, and relevance to substrate properties in various enzyme systems and metabolic pathways Acta. Biochim. Pol. 2004, 51, 493-531
    • (2004) Acta. Biochim. Pol. , vol.51 , pp. 493-531
    • Kulikowska, E.1    Kierdaszuk, B.2    Shugar, D.3
  • 51
    • 0035958502 scopus 로고    scopus 로고
    • Fluorescent charge-neutral analogue of xanthosine: Synthesis of a 2′-deoxyribonucleoside bearing a 5-aza-7-deazaxanthine base
    • Rao, P.; Benner, S. A. Fluorescent charge-neutral analogue of xanthosine: synthesis of a 2′-deoxyribonucleoside bearing a 5-aza-7-deazaxanthine base J. Org. Chem. 2001, 66, 5012-5015
    • (2001) J. Org. Chem. , vol.66 , pp. 5012-5015
    • Rao, P.1    Benner, S.A.2
  • 52
    • 0031004327 scopus 로고    scopus 로고
    • Theoretical and experimental study of isoguanine and isocytosine: Base pairing in an expanded genetic system
    • Roberts, C.; Bandaru, R.; Switzer, C. Theoretical and experimental study of isoguanine and isocytosine: Base pairing in an expanded genetic system J. Am. Chem. Soc. 1997, 119, 4640-4649
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 4640-4649
    • Roberts, C.1    Bandaru, R.2    Switzer, C.3
  • 53
    • 0000615415 scopus 로고
    • Site-specific enzymatic incorporation of an unnatural base, N6-(6-aminohexyl)isoguanosine, into RNA
    • Tor, Y.; Dervan, P. B. Site-specific enzymatic incorporation of an unnatural base, N6-(6-aminohexyl)isoguanosine, into RNA J. Am. Chem. Soc. 1993, 115, 4461-4467
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 4461-4467
    • Tor, Y.1    Dervan, P.B.2
  • 54
    • 0017198622 scopus 로고
    • Tautomerism of isoguanosine and solvent-induced keto-enol equilibrium
    • Sepiol, J.; Kazimierczuk, Z.; Shugar, D. Tautomerism of isoguanosine and solvent-induced keto-enol equilibrium Z. Naturforsch. 1976, 31, 361-370
    • (1976) Z. Naturforsch. , vol.31 , pp. 361-370
    • Sepiol, J.1    Kazimierczuk, Z.2    Shugar, D.3
  • 55
    • 2442675347 scopus 로고    scopus 로고
    • Artificial genetic systems: Exploiting the â€3; aromaticityâ€3; formalism to improve the tautomeric ratio for isoguanosine derivatives
    • Martinot, T. A.; Benner, S. A. Artificial genetic systems: exploiting the â€3;aromaticityâ€3; formalism to improve the tautomeric ratio for isoguanosine derivatives J. Org. Chem. 2004, 69, 3972-3975
    • (2004) J. Org. Chem. , vol.69 , pp. 3972-3975
    • Martinot, T.A.1    Benner, S.A.2
  • 56
    • 27244453121 scopus 로고    scopus 로고
    • The use of thymidine analogs to improve the replication of an extra DNA base pair: A synthetic biological system
    • Sismour, A. M.; Benner, S. A. The use of thymidine analogs to improve the replication of an extra DNA base pair: a synthetic biological system Nucleic Acids Res. 2005, 33, 5640-5646
    • (2005) Nucleic Acids Res. , vol.33 , pp. 5640-5646
    • Sismour, A.M.1    Benner, S.A.2
  • 58
    • 0014378880 scopus 로고
    • Origin of Genetic Code
    • Crick, F. H. C. Origin of Genetic Code J. Mol. Biol. 1968, 38, 367-379
    • (1968) J. Mol. Biol. , vol.38 , pp. 367-379
    • Crick, F.H.C.1
  • 59
    • 0014369024 scopus 로고
    • Evolution of the genetic apparatus
    • Orgel, L. E. Evolution of the genetic apparatus J. Mol. Biol. 1968, 38, 381-393
    • (1968) J. Mol. Biol. , vol.38 , pp. 381-393
    • Orgel, L.E.1
  • 60
    • 51249172502 scopus 로고
    • New Light on Tautomerism of Purines and Pyrimidines and Its Biological and Genetic-Implications
    • Shugar, D.; Kierdaszuk, B. New Light on Tautomerism of Purines and Pyrimidines and Its Biological and Genetic-Implications J. Biosci. 1985, 8, 657-668
    • (1985) J. Biosci. , vol.8 , pp. 657-668
    • Shugar, D.1    Kierdaszuk, B.2
  • 61
    • 0016844487 scopus 로고
    • Carbon-13 magnetic resonance. XXVI. A quantitative determination of the tautomeric populations of certain purines
    • Chenon, M. T.; Pugmire, R. J.; Grant, D. M.; Panzica, R. P.; Townsend, L. B. Carbon-13 magnetic resonance. XXVI. A quantitative determination of the tautomeric populations of certain purines J. Am. Chem. Soc. 1975, 97, 4636-4642
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 4636-4642
    • Chenon, M.T.1    Pugmire, R.J.2    Grant, D.M.3    Panzica, R.P.4    Townsend, L.B.5
  • 62
    • 0034718521 scopus 로고    scopus 로고
    • NMR structures of r(GCAGGCGUGC)2 and determinants of stability for single guanosine-guanosine base pairs
    • Burkard, M. E.; Turner, D. H. NMR structures of r(GCAGGCGUGC)2 and determinants of stability for single guanosine-guanosine base pairs Biochemistry 2000, 39, 11748-11762
    • (2000) Biochemistry , vol.39 , pp. 11748-11762
    • Burkard, M.E.1    Turner, D.H.2
  • 63
    • 0023957416 scopus 로고
    • An all-purine precursor of nucleic acids
    • Wachtershauser, G. An all-purine precursor of nucleic acids Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 1134-1135
    • (1988) Proc. Natl. Acad. Sci. U.S.A. , vol.85 , pp. 1134-1135
    • Wachtershauser, G.1
  • 66
    • 80053292275 scopus 로고    scopus 로고
    • Reversible bond formation enables the replication and amplification of a crosslinking salen complex as an orthogonal base pair
    • Kaul, C.; Muller, M.; Wagner, M.; Schneider, S.; Carell, T. Reversible bond formation enables the replication and amplification of a crosslinking salen complex as an orthogonal base pair Nat. Chem. 2011, 3, 794-800
    • (2011) Nat. Chem. , vol.3 , pp. 794-800
    • Kaul, C.1    Muller, M.2    Wagner, M.3    Schneider, S.4    Carell, T.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.