Base pairing of anhydrohexitol nucleosides with 2,6-diaminopurine, 5-methylcytosine and uracil as base moiety

Citation
V. Boudou et al., Base pairing of anhydrohexitol nucleosides with 2,6-diaminopurine, 5-methylcytosine and uracil as base moiety, NUCL ACID R, 27(6), 1999, pp. 1450-1456
Citations number
19
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Biochemistry & Biophysics
Journal title
NUCLEIC ACIDS RESEARCH
ISSN journal
0305-1048 → ACNP
Volume
27
Issue
6
Year of publication
1999
Pages
1450 - 1456
Database
ISI
SICI code
0305-1048(19990315)27:6<1450:BPOANW>2.0.ZU;2-F
Abstract
Hexitol nucleic acids (HNAs) with modified bases (5-methylcytosine, 2,6-dia minopurine or uracil) were synthesized, The introduction of the 5-methylcyt osine base demonstrates that N-benzoylated 5-methylcytosylhexitol occurs as the imino tautomer. The base pairing systems (G:C-Me, U:D, Tn and U:A) obe y Watson-Crick rules. Substituting hT for hU, hC(Me) for hC and hD for hA g enerally leads to increased duplex stability. In a single case, replacement of hC by hCMe did not result in duplex stabilization, This sequence-specif ic effect could be explained by the geometry of the model duplex used for c arrying out the thermal stability study. Generally, polypurine HNA sequence s give more stable duplexes with their RNA complement than polypyrimidine H NA sequences, This observation supports the hypothesis that, besides change s in stacking pattern, the difference in conformational stress between puri ne and pyrimidine nucleosides may contribute to duplex stability, Introduct ion of hC(Me) and hD in HNA sequences further increases the potential of HN A to function as a steric blocking agent.