Document Detail

Silver(I)-mediated cytosine self-pairing is preferred over hoogsteen-type base pairs with the artificial nucleobase 1,3-dideaza-6-nitropurine.
MedLine Citation:
PMID:  20391190     Owner:  NLM     Status:  MEDLINE    
A 2'-deoxyribonucleoside containing 1,3-dideaza-6-nitropurine was synthesized and incorporated into oligonucleotides. The acid-base properties of this nucleoside and the corresponding N9-methylated derivative were investigated by pD-dependent (1)H NMR spectroscopy. A possible formation of Hoogsteen-type base pairs with cytosine was studied by ultraviolet (UV) and circular dichroism (CD) spectroscopy in the presence and absence of Ag(I) and under neutral and acidic conditions, respectively. In each case, no indication for the formation of Hoogsteen-type base pairs was obtained, which is attributed to the higher affinity of cytosine to form self-complementary hemi-protonated base pairs under acidic conditions and metal-mediated homo base pairs in presence of Ag(I), respectively.
Dominik A Megger; Jens Muller
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Nucleosides, nucleotides & nucleic acids     Volume:  29     ISSN:  1532-2335     ISO Abbreviation:  Nucleosides Nucleotides Nucleic Acids     Publication Date:  2010 Jan 
Date Detail:
Created Date:  2010-04-14     Completed Date:  2010-09-27     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100892832     Medline TA:  Nucleosides Nucleotides Nucleic Acids     Country:  England    
Other Details:
Languages:  eng     Pagination:  27-38     Citation Subset:  IM    
Westfalische Wilhelms-Universitat Munster, Institut fur Anorganische und Analytische Chemie, Munster, Germany.
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MeSH Terms
Base Pairing*
Base Sequence
Benzimidazoles / chemistry*
Circular Dichroism
Cytosine / metabolism*
Hydrogen-Ion Concentration
Molecular Sequence Data
Nucleic Acid Denaturation
Nucleic Acid Heteroduplexes
Oligonucleotides / chemistry,  genetics
Purines / chemistry*
Silver Nitrate / chemistry*
Reg. No./Substance:
0/Benzimidazoles; 0/Nucleic Acid Heteroduplexes; 0/Oligonucleotides; 0/Purines; 71-30-7/Cytosine; 7761-88-8/Silver Nitrate

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