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Volumn 125, Issue 52, 2003, Pages 16408-16415

NMR Study on the Photoresponsive DNA Tethering an Azobenzene. Assignment of the Absolute Configuration of Two Diastereomers and Structure Determination of Their Duplexes in the trans-Form

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; CONFORMATIONS; DNA; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INTERCALATION COMPOUNDS; MELTING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMICAL REACTIONS; PROTONS; STEREOCHEMISTRY;

EID: 0347064289     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja037248j     Document Type: Article
Times cited : (100)

References (24)
  • 8
    • 0346843858 scopus 로고    scopus 로고
    • note
    • By this combination, X residue is additionally incorporated into the natural full-matched 6-mer duplex.
  • 9
    • 0346213278 scopus 로고    scopus 로고
    • note
    • Although 1D and 2D NMR spectra of the duplex containing cis-azobenzene were also measured, the spectra were too complicated to be solved because of the thermal instability of the duplex of the cis-form and the influence of the much more stable trans-form duplex (only 70% is isomerized to the cis-form under the conditions employed).
  • 10
    • 0347474505 scopus 로고    scopus 로고
    • note
    • Proton signals of the pairs of 2 and 6, 3 and 5, 8 and 12, and 9 and 11 on the azobenzene were equivalent to each other even in the duplex.
  • 11
    • 0346213279 scopus 로고    scopus 로고
    • note
    • All of the NOEs concerning the azobenzene are displayed with lines on the structure in Supporting Information Figure 1.
  • 12
    • 0346213283 scopus 로고    scopus 로고
    • note
    • Stereoviews of the duplexes from other angles are shown in Supporting Information Figure 2.
  • 13
    • 0348104412 scopus 로고    scopus 로고
    • note
    • The melting curves of both Azo-α/C and Azo-β/C duplexes either in the trans- or in the cis-form are presented in Supporting Information Figure 3.
  • 14
    • 0035898477 scopus 로고    scopus 로고
    • Azobenzene was tethered on the chiral threoninol that has a structure similar to that of the present prochiral 2,2-bis(hydroxymethyl)propionic acid (Asanuma, H.; Takarada, T.; Yoshida, T.; Tamaru, D.; Liang, X.; Komiyama, M. Angew. Chem., Int. Ed. 2001, 40, 2671-2673). A similar dependence in melting temperature (R-form > S-form) for the chirality of the linker was observed. See Supporting Information Scheme. 1 and Supporting Information Table 1.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 2671-2673
    • Asanuma, H.1    Takarada, T.2    Yoshida, T.3    Tamaru, D.4    Liang, X.5    Komiyama, M.6
  • 15
    • 0346843851 scopus 로고    scopus 로고
    • note
    • In the present paper, the X residue is additionally incorporated into one strand of the full-matched natural double strands (7-mer/6-mer nonsymmetrical combination). However, placement of a nucleobase as the counterpart of the X residue, such as a 5′-CGAXGTC-3′/3′ -GCTTCAG-5′ (7-mer/7-mer symmetrical combination) duplex, destabilizes the duplex because intercalated trans-azobenzene directly faces the extra nucleobase and a mismatch-like structure is formed.
  • 19
    • 0347474503 scopus 로고    scopus 로고
    • note
    • 2O by use of a 3-9-19 WATER-GATE pulse sequence and confirmed that the sets of restraints for the calculation obtained from Jump and Return and WATERGATE were almost the same.
  • 22
    • 0346213277 scopus 로고    scopus 로고
    • note
    • This result indicates that spin diffusion at 100 ms is still small and does not affect the distance interpretation. Note that the loose restraints were used for structural calculations.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.