Post-modification of triazole-linked analogues of dna for positively charged variants

Heterocycles

Volumn 87, Issue 5, 2013, Pages 1023-1028

  Fujino, Tomoko ^a   Miyauchi, Yusuke ^a   Tsunaka, Nobuhide ^a   Okada, Koudai ^a   Isobe, Hiroyuki ^a  

^a TOHOKU UNIVERSITY   (Japan)

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[No Author keywords available]

Indexed keywords

EID: 84876896887     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-13-12697     Document Type: Article

References (19)

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8. The yield of tetramer 2b was lower than other cases, because the compound was amphiphilic and therefore dissolved slightly in organic solvents used for precipitation. 6. The saturated solution was prepared as follows: The compound was immersed in SSPE buffer at 50 °C and stirred for 3 h. After gradually cooling the solution to ambient temperature, precipitates were removed by filtration with membrane filter (pore size 200 nm) to afford the saturated solution. 7. We do not understand the detailed mechanism of the condition-dependency of the melting curves at this stage. However, similar effects were observed with cationic guanidium oligonucleotides, which may suggest that the stronger electrostatic interactions with natural strands may affect the helix formation. See for instance: (a) R. O. Dempcy, K. A. Browne, and T. C. Bruice, Proc. Natl. Acad. Sci. USA, 1995, 92, 6097
9. b) A. Blaskó, R. O. Dempcy, E. E. Minyat, and T. C. Bruice, J. Am. Chem. Soc., 1996, 118, 7892.
10. No triplex formation has been detected with electroneutral TLDNA under identical conditions. The electronic complementarity between natural DNA and TLDNA+ may have facilitated the triplex formation. Similar effects were observed in the neutral thiourea-linked oligonucleotide and cationic S-methylthiourea-linked oligonucleotide. See: D. P. Arya and T. C. Bruice, Bioorg. Med. Chem. Lett., 2000, 10, 691.
11. The hyperchromicity of TLDNA upon melting tends to be smaller than that of natural DNA, which has been also observed with the duplex of electroneutral congeners (ref. 1). 10. The Tm values were obtained by calculation of inflection points of the melting curve using a melting program (VWTP-780) from JASCO. 11
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14. We calculated the theoretical Tm value of (dT)5•(dA)5 duplex with the following equation: ΔH/{ΔS + 1.987 ln(Ct/4)} - 273.15 + 12.5 log[Na+] where Ct is the total strand concentration. See: J. SantaLucia, Jr., H. T. Allawi, and P. A. Seneviratne, Biochemistry, 1996, 35, 3555.
15. Electroneutral 10-mer TLDNA recorded the Tm value of 61.1 °C (ref. 1). 14
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