Literature DB >> 8807846

Bicyclo-DNA: a Hoogsteen-selective pairing system.

M Bolli1, J C Litten, R Schütz, C J Leumann.   

Abstract

BACKGROUND: The natural nucleic acids (DNA and RNA) can adopt a variety of structures besides the antiparallel double helix described by Watson and Crick, depending on base sequence and solvent conditions. Specifically base-paired DNA structures with regular backbone units include left-handed and parallel duplexes and triple and quadruple helical arrangements. Given the base-pairing pattern of the natural bases, preferences for how single strands associate are determined by the structure and flexibility of the sugar-phosphate backbone. We set out to determine the role of the backbone in complex formation by designing DNA analogs with well defined modifications in backbone structure.
RESULTS: We recently developed a DNA analog (bicyclo-DNA) in which one (gamma) of the six torsion angles (alpha-zeta) describing the DNA-backbone conformation is fixed in an orientation that deviates from that observed in B-DNA duplexes by about + 100 degrees , a shift from the synclinal to the antiperiplanar range. Upon duplex formation between homopurine and homopyrimidine sequences, this analog preferentially selects the Hoogsteen and reversed Hoogsteen mode, forming A-T and G-C+ base pairs. Base-pair formation is highly selective, but degeneracy is observed with respect to strand orientation in the duplex.
CONCLUSIONS: The flexibility and orientation of the DNA backbone can influence the preferences of the natural bases for base-pairing modes, and can alter the relative stability of duplexes and triplexes.

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Year:  1996        PMID: 8807846     DOI: 10.1016/s1074-5521(96)90263-x

Source DB:  PubMed          Journal:  Chem Biol        ISSN: 1074-5521


  6 in total

1.  Nucleic acid duplexes incorporating a dissociable covalent base pair.

Authors:  K Gao; L E Orgel
Journal:  Proc Natl Acad Sci U S A       Date:  1999-12-21       Impact factor: 11.205

2.  Watson-Crick base-pairing properties of bicyclo-DNA.

Authors:  M Bolli; H U Trafelet; C Leumann
Journal:  Nucleic Acids Res       Date:  1996-12-01       Impact factor: 16.971

3.  A historical account of Hoogsteen base-pairs in duplex DNA.

Authors:  Evgenia N Nikolova; Huiqing Zhou; Federico L Gottardo; Heidi S Alvey; Isaac J Kimsey; Hashim M Al-Hashimi
Journal:  Biopolymers       Date:  2013-12       Impact factor: 2.505

4.  Role of pK(a) of nucleobases in the origins of chemical evolution.

Authors:  Ramanarayanan Krishnamurthy
Journal:  Acc Chem Res       Date:  2012-04-26       Impact factor: 22.384

5.  (C2G4)n repeat expansion sequences from the C9orf72 gene form an unusual DNA higher-order structure in the pH range of 5-6.

Authors:  Prince Kumar Lat; Dipankar Sen
Journal:  PLoS One       Date:  2018-06-18       Impact factor: 3.240

Review 6.  The Medicinal Chemistry of Artificial Nucleic Acids and Therapeutic Oligonucleotides.

Authors:  Miklós Bege; Anikó Borbás
Journal:  Pharmaceuticals (Basel)       Date:  2022-07-22
  6 in total

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