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Titolo:
THE STRUCTURE OF D(TPA)ASTERISK, THE MAJOR PHOTOPRODUCT OF THYMIDYLYL-(3'-5')-DEOXYADENOSINE
Autore:
ZHAO XD; NADJI S; KAO JLF; TAYLOR JS;
Indirizzi:
WASHINGTON UNIV,DEPT CHEM ST LOUIS MO 63130 WASHINGTON UNIV,DEPT CHEM ST LOUIS MO 63130 WASHINGTON UNIV,CHEM DEPT HIGH RESOLUT NMR FACIL ST LOUIS MO 63130
Titolo Testata:
Nucleic acids research
fascicolo: 8, volume: 24, anno: 1996,
pagine: 1554 - 1560
SICI:
0305-1048(1996)24:8<1554:TSODTM>2.0.ZU;2-F
Fonte:
ISI
Lingua:
ENG
Soggetto:
C-13-NMR CHEMICAL-SHIFTS; SOLUTION-STATE STRUCTURE; CROSS-RELAXATION; ORGANIC-COMPOUNDS; NMR-SPECTROSCOPY; AQUEOUS-SOLUTION; PARAMETER SET; CARBON-ATOMS; THYMIDYLYL-(3'->5')-THYMIDINE; PREDICTION;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
27
Recensione:
Indirizzi per estratti:
Citazione:
X.D. Zhao et al., "THE STRUCTURE OF D(TPA)ASTERISK, THE MAJOR PHOTOPRODUCT OF THYMIDYLYL-(3'-5')-DEOXYADENOSINE", Nucleic acids research, 24(8), 1996, pp. 1554-1560

Abstract

Irradiation of the dinucleotide TpdA and TA-containing oligonucleotides and DNA produces the TA photoproduct which was proposed to be the [2+2] cycloaddition adduct between the C5-C6 double bonds of the T andthe A [Bose,S.N., Kumar,S., Davies,R.J.H., Sethi,S.K. and McCloskey,J. A. (1984) Nucleic Acids Res. 12, 7929-7947], The proposed structure was based on a variety of spectroscopic and chemical degradation studies, and the assignment of a trans-syn-I stereochemistry was based on anextensive H-1-NMR and molecular modeling study of the dinucleotide adduct [Koning,T.M.G., Davies,R.J.H. and Kaptein,R. (1990) Nucleic AcidsRes, 18, 277-284], However, a number of properties of TA are not in accord with the originally proposed structure, and prompted a re-evaluation of the structure, To assign the C-13 spectrum and establish the bond connectivities of the TA photoproduct of TpdA [d(TpA)*], H-1-C-13 heteronuclear multiple-quantum coherence (HMQC) and heteronuclear multiple bond correlation (HMBC) spectra were obtained. The C-13 shifts and connectivities were found to be inconsistent with the originally proposed cyclobutane ring fusion between the thymine and adenine, but could be explained by a subsequent ring-expansion reaction to give an eight-membered ring valence isomer, The new structure for the d(TpA) resolves the inconsistencies with the originally proposed structure, and could have a stereochemistry that arises from the anti, anti glycosyl conformation found in B form DNA.

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Documento generato il 25/01/20 alle ore 16:41:14