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N(7)-protonation-induced conformational flipping in hypermodified nucleic acid base N6-(N-glycylcarbonyl) adenine

โœ Scribed by Ravindra Tewari

Book ID
103033314
Publisher
Elsevier Science
Year
1995
Tongue
English
Weight
361 KB
Volume
238
Category
Article
ISSN
0009-2614

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โœฆ Synopsis

Protonation-induced conformational changes are studied in the hypermodified nucleic acid base N6-(N-glycylcarbonyl) adenine, gc6Ade, using the quantum chemical perturbative configuration interaction using localised orbitals method. Protonation at the N(7) position of adenine in gc6Ade induces reorientation of the N 6 substituent, so as to allow stabilisation through an intramolecular hydrogen bond involving N(7)H and the carbonyl oxygen in the glycylcarbonyl substituent. The relative orientation of the carboxyl group with respect to the carbonyl group in the ureido HN-CO-NH linkage is predicted to be similar to that in unprotonated gc6Ade. The theoretically preferred proximal conformation of N(7)-protonated gc6Ade restores the participation of N(6)H and N(1) in the Watson-Crick base pairing similar to that in unmodified adenine. This unique orientation can be significant for altering the reading frame in codon-anticodon interactions.

๐Ÿ“œ SIMILAR VOLUMES

N(7)-protonation induced conformational
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3ะˆ-side with four bases of mRNA, permitting an altered selection of the codon triplet. 6 6 ลฝ . However, another derivative, m tc Ade, because of the methyl group replacing the N 6 hydrogen, cannot base pair with uridine and should maintain the reading frame ลฝ .

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The influence of protonation at N 1 on the conformational preferences ลฝ . 6 ลฝ . of the N 6 substituent in the modified nucleic acid base N -N-glycylcarbonyl adenine, gc 6 Ade, was investigated by the quantum chemical perturbative configuration interaction ลฝ . using localized orbitals PCILO method.

Conformational flipping of the N(6) subs
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Conformational transitions of the N(6) substituent, in hypermodified nucleic acid base N 6 -(N-glycylcarbonyl)adenine, gc 6 Ade, on diprotonation of the adenine ring at any two of N(1), N(3), and N(7) sites, are studied using the quantum chemical perturbative configuration interaction with localized