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Nebularine (purine riboside) lacks exocyclic functional groups and offers an altered hydrogen bonding scheme while retaining base stacking ability.(1) It can be viewed as an adenosine analogue with the hydrogen bond donor deleted. Sequential replacement of conserved adenosine residues in hammerhead ribozymes by nebularine residues1c,d suggested the presence of interstrand non-Watson-Crick hydrogen bonding.1c Depending on the position of the nebularine residue, cleavage rates were either unchanged or diminished.1c,d Incorporation of nebularine into a GNRA tetraloop has also been useful for studying this type of RNA structural feature.1e Nebularine has been installed into RNA using two different phosphoramidites, one with 2'-O-THP protection1a and one with 2'-O-TBDMS protection.1b-e We offer the latter, Nebularine-CE Phosphoramidite (BA0265) as well as the 2-deoxy version (BA0016).
- (a) SantaLucia, J., Jr.; Kierzek, R.; Turner, D. H. J. Am. Chem. Soc. 1991, 113, 4313-4322. (b) Slim, G.; Pritchard, C.; Biala, E.; Asseline, U.; Gait, M. J. Nucleic Acids Symp. Ser. 1991, 24, 55-58. (c) Slim, G.; Gait, M. J. Biochem. Biophys. Res. Commun. 1991, 183, 605-609. (d) Fu, D.-J.; Rajur, S.; McLaughlin, L. W. Biochemistry 1993, 32, 10629-10673. (e) Wörner, K.; Strube, T.; Engels, J. W. Helv. Chim. Acta 1999, 82, 2094-2104.
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