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BA 0265
Product Information Molecular Structure

Nebularine CEP

Notes: Nebularine (purine riboside) is an adenosine analog with the hydrogen bond donor deleted. This nucleobase scaffold offers an altered hydrogen bonding scheme while retaining base stacking ability.

Description: Nebularine (purine riboside) lacks exocyclic functional groups and offers an altered hydrogen bonding scheme while retaining base stacking ability.1-4 It can be viewed as an adenosine analog with the hydrogen bond donor deleted. Sequential replacement of conserved adenosine residues in hammerhead ribozymes by nebularine residues2b,3 suggested the presence of interstrand non-Watson-Crick hydrogen bonding.2b Depending on the position of the nebularine residue, cleavage rates were either unchanged or diminished.2b,3 Incorporation of nebularine into a GNRA tetraloop has also been useful for studying this type of RNA structural feature.4 Nebularine has been installed into RNA using two different phosphoramidites, one with 2'-O-THP protection1 and one with 2'-O-TBDMS protection.2-4 We offer the latter, Nebularine CEP (BA 0265, download Product Information) as well as the 2-deoxy version, 2'-Deoxynebularine CEP (BA 0016).

(1) SantaLucia, J., Jr.; Kierzek, R.; Turner, D. H. J. Am. Chem. Soc. 1991, 113, 4313-4322.
(2) (a) Slim, G.; Pritchard, C.; Biala, E.; Asseline, U.; Gait, M. J. Nucleic Acids Symp. Ser. 1991, 24, 55-58. (b) Slim, G.; Gait, M. J. Biochem. Biophys. Res. Commun. 1991, 183, 605-609.
(3) Fu, D.-J.; Rajur, S.; McLaughlin, L. W. Biochemistry 1993, 32, 10629-10673.
(4) Wörner, K.; Strube, T.; Engels, J. W. Helv. Chim. Acta 1999, 82, 2094-2104.

Nebularine CEP
Product Details Product Pricing

MF: C46H61N6O7PSi

MW: 869.07

CAS NO: 151132-95-5

Storage Conditions: -20 oC, dry

Purity≥95%

Availability: 

Stock maintained. Ships within 1-3 days.

Alternate Name: 

9-[2-O-t-Butyldimethylsilyl-3-O-
[(diisopropylamino)(2-cyanoethoxy)phosphino]-5-O-
(4,4'-dimethoxytrityl)-beta-D-ribofuranosyl]-9H-
purine

Alternate Name: 

Purine Riboside CEP, or P CEP
Unit Weight Unit Price Quantity
50 µmol $245.00
100 µmol $405.00
0.25 g $895.00
 
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