Affinity labeling of a single guanine bulge

Journal of the American Chemical Society

Volumn 125, Issue 30, 2003, Pages 8972-8973

  Nakatani, Kazuhiko ^a,b   Horie, Souta ^a   Saito, Isao ^a  

^a KYOTO UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GUANINE; NAPHTHYRIDINE DERIVATIVE;

AFFINITY LABELING; ARTICLE; BASE MISPAIRING; DNA HYBRIDIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; SINGLE NUCLEOTIDE POLYMORPHISM; THERMODYNAMICS;

AFFINITY LABELS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA; DNA PROBES; GUANINE; NAPHTHYRIDINES; NUCLEIC ACID HYBRIDIZATION; SPECTROMETRY, FLUORESCENCE;

EID: 0042868749     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0350740     Document Type: Article

References (17)

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14. A proposed reaction scheme involving a nucleophilic addition of the secondary amino nitrogen to C8 of the alkylated guanine for the isomerization of 2-TGT to 2-TGTx is shown in Scheme S2.
15. N7 of the guanine directly hydrogen bonded to 2 was found not to be nucleophilic to the epoxide. This is most likely due to an electronwithdrawing effect of naphthyridine chromophore. HOMO energies of guanine hydrogen-bonded to cytosine and 2 calculated at B3LYP/6-31G are -4.82 and -5.11 eV, respectively, showing a considerable lowering of the HOMO energy level upon 2-binding.
16. It was confirmed separately that 2-amino-1,8-naphthyridine was stable under the conditions, and hydrolysate of TGT under the conditions did not produce any fluorescence at 396 nm.
17. The use of an excess amount of 2 or hybridization probe results in an increase of the background level of the labeling reaction.