메뉴 건너뛰기




Volumn 46, Issue 14, 2007, Pages 2478-2484

Mapping the landscape of potentially primordial informational oligomers: Oligodipeptides tagged with 2,4-disubstituted 5-aminopyrimidines as recognition elements

Author keywords

5 aminopyrimidines; Base pairing; DNA; Nucleic acid hybridization; Oligonucleotides

Indexed keywords

DNA; MAPPING; PEPTIDES; REACTION KINETICS;

EID: 34250633363     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200603209     Document Type: Article
Times cited : (70)

References (55)
  • 2
    • 34250878397 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2007, 46, 2470.
    • (2007) Chem. Int. Ed , vol.46 , pp. 2470
    • Angew1
  • 13
    • 0014413584 scopus 로고
    • For alternative (potentially prebiotic) formation of canonical pyrimidine, see, for example: a
    • For alternative (potentially prebiotic) formation of canonical pyrimidine, see, for example: a) J. P. Ferris, R. A. Sanchez, L. E. Orgel, J. Mol. Biol. 1968, 33, 693;
    • (1968) J. Mol. Biol , vol.33 , pp. 693
    • Ferris, J.P.1    Sanchez, R.A.2    Orgel, L.E.3
  • 18
    • 34250886493 scopus 로고
    • For 5-aminoisocytosine, see: d
    • For 5-aminoisocytosine, see: d) T. B. Johnson, C. O. Johns, Am. Chem. J. 1905, 34, 554;
    • (1905) Am. Chem. J , vol.34 , pp. 554
    • Johnson, T.B.1    Johns, C.O.2
  • 20
    • 34250846632 scopus 로고
    • For 2,4,5-triaminopyrimidine, see f, 109. 5-Aminouracil is commercially available
    • For 2,4,5-triaminopyrimidine, see f) D. J. Brown, J. Appl. Chem. 1957, 7, 109. 5-Aminouracil is commercially available.
    • (1957) J. Appl. Chem , vol.7
    • Brown, D.J.1
  • 26
    • 0025008851 scopus 로고
    • For an early constitutional analysis of alternative nucleobase pairs, see: a
    • For an early constitutional analysis of alternative nucleobase pairs, see: a) J. A. Piccirilli, T. Krauch, S. E. Moroney, S. E. Benner, Nature 1990, 343, 33;
    • (1990) Nature , vol.343 , pp. 33
    • Piccirilli, J.A.1    Krauch, T.2    Moroney, S.E.3    Benner, S.E.4
  • 28
    • 0346731227 scopus 로고    scopus 로고
    • T. Otzen, E. G. Wempe, B. Kunz, R. Bartels, G. L. -Yvetot, W. Hansel, K.-J. Schaper, J. K. Seydel, J. Med. Chem. 2004, 47, 240;
    • a) T. Otzen, E. G. Wempe, B. Kunz, R. Bartels, G. L. -Yvetot, W. Hansel, K.-J. Schaper, J. K. Seydel, J. Med. Chem. 2004, 47, 240;
  • 30
    • 0021964986 scopus 로고    scopus 로고
    • D. J. Brown, K. Mori, Aust. J. Chem. 1985, 38, 467. An amino group in position 5 of a pyrimidine is, together with the NH group in position 1, part of a vinylogous hydrazine system, whereas amino groups at position 2 or 4 are part of a guanidine or an amidine system, respectively.
    • c) D. J. Brown, K. Mori, Aust. J. Chem. 1985, 38, 467. An amino group in position 5 of a pyrimidine is, together with the NH group in position 1, part of a vinylogous hydrazine system, whereas amino groups at position 2 or 4 are part of a guanidine or an amidine system, respectively.
  • 32
    • 0034742736 scopus 로고    scopus 로고
    • The procedure used in the preparation for the D enantiomer was used: K. L. Webster, A. B. Maude, M. E. O'Donnell, A. P. Mehorotra, D. Gani, J. Chem. Soc. Perkin Trans. 1 2001, 1673.
    • b) The procedure used in the preparation for the D enantiomer was used: K. L. Webster, A. B. Maude, M. E. O'Donnell, A. P. Mehorotra, D. Gani, J. Chem. Soc. Perkin Trans. 1 2001, 1673.
  • 34
    • 34250801049 scopus 로고    scopus 로고
    • [13]
    • [13]
  • 36
    • 34250903166 scopus 로고    scopus 로고
    • The similarity between the UV spectra of cytosine (λmax, 267 nm, ε, 6100)[15a] and 1-methyl-cytosine (λmax, 273 nm, ε, 8100)[15a] or 1-ribofuranosylcytosine (λmax, 270 nm, ε, 8800, 15b] closely corresponds to the similarity between the UV spectra of the 5-aminocytosine (λmax, 292 nm, ε, 3800, 15c] and of its 1-ribofuranosyl derivative (λmax, 298 nm, ε, 6200)[15b] in buffer solution pH 7. This indicates that the 5-aminocytosine nucleus prefers the position 1 NH tautomer in aqueous solution. In the 5-aminoisocytosine series we observe UV spectra of quite different structure for the free base 2 (λmax, 287 nm, ε, 4100; 240 nm (shoulder, ε, 6400; ε220nm, 10,500) and its N3 methyl derivative λmax, 308 and 242 nm, ε, 7300 and 6800;
    • 220nm = 5200) relative to the maxima of the 3-methylisocytosine derivative. The spectrum is, however, of the same type as for the free N-3-methylated base. These findings point to the conclusion that 5-aminoisocytosine disfavors its NH(3)-tautomer in aqueous solution. The conclusion remains tentative as the necessary UV comparison with the 1-methylisocytosine derivative is lacking.
  • 43
    • 0031004327 scopus 로고    scopus 로고
    • C. Roberts, R. Bandaru, C. Switzer, J. Am. Chem. Soc. 1997, 119, 4640. In both the homo-DNA and the pyranosyl-RNA series, it has been shown that isoguanine can form strong Watson - Crick pairs with guanine. This demonstrates the capability of the isoguanine nucleus to act in base pairing as the position 3 NH tautomer (see references [16] and [17a]). It should be noted, however, that the generation of such a guanine - isoguanine pair from guanine and the isoguanine position 3 NH tautomer might well be indistinguishable from that of an identical pair from guanine and the phenolic isoguanine tautomer (see the discussion on pages 438-444 in reference [17a]).
    • b) C. Roberts, R. Bandaru, C. Switzer, J. Am. Chem. Soc. 1997, 119, 4640. In both the homo-DNA and the pyranosyl-RNA series, it has been shown that isoguanine can form strong Watson - Crick pairs with guanine. This demonstrates the capability of the isoguanine nucleus to act in base pairing as the position 3 NH tautomer (see references [16] and [17a]). It should be noted, however, that the generation of such a guanine - isoguanine pair from guanine and the isoguanine position 3 NH tautomer might well be indistinguishable from that of an identical pair from guanine and the phenolic isoguanine tautomer (see the discussion on pages 438-444 in reference [17a]).
  • 44
    • 34250884757 scopus 로고    scopus 로고
    • We surmise that, in this guanine-cytosine-like pairing interaction, it is the 2-amino-4-oxo member that takes the role of the guanine-analogue; the argument being that, if the 2-oxo-4-amino member would fulfill that role, it would have to do so as its position 3 NH tautomer, in which the location of two amino functions at a common C-C double bond should be electronically unfavorable (local four-center, six-electron system).
    • We surmise that, in this guanine-cytosine-like pairing interaction, it is the 2-amino-4-oxo member that takes the role of the guanine-analogue; the argument being that, if the 2-oxo-4-amino member would fulfill that role, it would have to do so as its position 3 NH tautomer, in which the location of two amino functions at a common C-C double bond should be electronically unfavorable (local four-center, six-electron system).
  • 45
    • 34250833505 scopus 로고    scopus 로고
    • J. Jonas, J. Gut, Collect. Czech. Chem. Commun. 1962, 27, 716.
    • J. Jonas, J. Gut, Collect. Czech. Chem. Commun. 1962, 27, 716.
  • 48
    • 34250875289 scopus 로고    scopus 로고
    • Spectroscopically determined from the pH-dependent UV spectrum. For details, see the Supporting Information of reference [1].
    • Supporting Information of reference , vol.1
  • 50
    • 0002453698 scopus 로고    scopus 로고
    • For a review of factors that determine base-pairing strength in nonaqueous medium, see
    • For a review of factors that determine base-pairing strength in nonaqueous medium, see: S. C. Zimmermann, P. S. Corbin, Struct. Bonding (Berlin) 2000, 96, 63.
    • (2000) Struct. Bonding (Berlin) , vol.96 , pp. 63
    • Zimmermann, S.C.1    Corbin, P.S.2
  • 51
    • 34250880360 scopus 로고    scopus 로고
    • a values and the formation of short hydrogen bonds in the solid state, see: T. Steiner, I. Majerz, C. C. Wilson, Angew. Chem. 2001, 113, 2728;
    • a values and the formation of short hydrogen bonds in the solid state, see: T. Steiner, I. Majerz, C. C. Wilson, Angew. Chem. 2001, 113, 2728;
  • 52
    • 0035898337 scopus 로고    scopus 로고
    • a match) has recently been proposed to explain the fact that, as a rule, RNA duplexes have higher melting temperatures than corresponding DNA duplexes;
    • a match") has recently been proposed to explain the fact that, as a rule, RNA duplexes have higher melting temperatures than corresponding DNA duplexes;
  • 55
    • 0025025654 scopus 로고    scopus 로고
    • Studies along these lines are being carried out in collaboration with J. Rebek (TSRI). See also in this context: K. S. Jeong, T. Tjivikua, J. Rebek, Jr., J. Am. Chem. Soc. 1990, 112, 3215.
    • Studies along these lines are being carried out in collaboration with J. Rebek (TSRI). See also in this context: K. S. Jeong, T. Tjivikua, J. Rebek, Jr., J. Am. Chem. Soc. 1990, 112, 3215.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.