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Titolo:
Structure of an 11-mer DNA duplex containing the carbocyclic nucleotide analog: 2 '-deoxyaristeromycin
Autore:
Smirnov, S; Johnson, F; Marumoto, R; de los Santos, C;
Indirizzi:
SUNY Stony Brook, Dept Pharmacol Sci, Stony Brook, NY 11794 USA SUNY StonyBrook Stony Brook NY USA 11794 Sci, Stony Brook, NY 11794 USA Takeda Chem Ind Ltd, Anim Hlth Res Labs, Yodogawa Ku, Osaka 532, Japan Takeda Chem Ind Ltd Osaka Japan 532 Labs, Yodogawa Ku, Osaka 532, Japan
Titolo Testata:
JOURNAL OF BIOMOLECULAR STRUCTURE & DYNAMICS
fascicolo: 6, volume: 17, anno: 2000,
pagine: 981 - 991
SICI:
0739-1102(200006)17:6<981:SOA1DD>2.0.ZU;2-W
Fonte:
ISI
Lingua:
ENG
Soggetto:
L-HOMOCYSTEINE HYDROLASE; NUCLEIC-ACIDS; NEPLANOCIN-A; NMR; NUCLEOSIDES; DERIVATIVES; OLIGONUCLEOTIDES; INHIBITORS; RELAXATION; REFINEMENT;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Citazioni:
30
Recensione:
Indirizzi per estratti:
Indirizzo: Smirnov, S SUNY Stony Brook, Dept Pharmacol Sci, Stony Brook, NY 11794 USASUNY Stony Brook Stony Brook NY USA 11794 Brook, NY 11794 USA
Citazione:
S. Smirnov et al., "Structure of an 11-mer DNA duplex containing the carbocyclic nucleotide analog: 2 '-deoxyaristeromycin", J BIO STRUC, 17(6), 2000, pp. 981-991

Abstract

2'-deoxyaristeromycin (dAr) is a nucleoside analogue that is resistant to the action of DNA glycosylases. High-resolution NMR spectroscopy and molecular dynamics simulations were used to determine the three-dimensional structure of an Il-mer DNA containing a single dAr.T base pair at its center. Analysis of the spectra revealed the existence of a right-handed duplex in solution, stabilized by Watson-Crick hydrogen bonding and base-stacking interactions. The carbocyclic sugar adopted a Cl'-Exo conformation and sugars ofthe 3'-flanking base pair had puckers in the O4'-endo range. The dAr.T base pair was mildly propeller twisted, and the dAr analogue showed a positiveroll with the 3'-flanking base. Our findings indicate that the observed resistance of dAr-containing oligodeoxynucleotides to the catalytic action ofDNA glycosylases relates to its electronic properties rather than structure, and validate the use of dAr and related carbocyclic nucleoside analoguesfor biological and structure/function relationship studies.

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Documento generato il 01/12/20 alle ore 16:12:37