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BA 0266
Product Information Molecular Structure

2-Aminopurine riboside CEP

Notes: Guanosine analog which lacks the O6 carbonyl resulting in a hydrogen bonding pattern isomeric with that of adenosine.

Description: Deletion of the O6 carbonyl group of guanosine results in 2-aminopurine riboside (2-AP). The hydrogen bonding pattern of the 2-aminopurine nucleobase (N1 acceptor, H-N2 donor) is isomeric with that of adenosine (N1 acceptor, H-N6 donor). This nucleoside allows the study of the role of exocyclic functional groups, base stacking, and hydrogen bonding patterns in purine-containing nucleic acids. For example, replacement of guanosine residues with 2-AP in the core region of hammerhead ribozymes was useful in determining their role in stabilizing the transition state of ribozyme cleavage.1 The nature of hydrogen-bonding between G-A mismatches in RNA internal loops was studied with 2-AP.2 The role of hydrogen-bonding and stacking interactions in the stability of GNRA loops was probed using 2-AP substitutions.3 The thermodynamic parameters for RNA loops of the type (A)n were determined using time-resolved spectrofluorimetry on RNAs bearing 2-AP residues in place of A residues, since 2-AP is blue fluorescent and was found to have properties in the (A)n region that were otherwise very similar to adenosine.4 In this sense, 2-AP can be used as a non-invasive conformational probe in RNA studies. Of the different phosphoramidites that have been used for 2-aminopurine riboside incorporation into RNA oligonucleotides,1-5 we have chosen to offer 2-Aminopurine riboside CEP in the particular form shown,1,4 which appears to offer the best results in RNA synthesis yield and purity. Download Product Information.

(1) Tuschl, T.; Ng, M. M. P.; Pieken, W.; Benseler, F.; Eckstein, F. Biochemistry 1993, 32, 11658-11668.
(2) SantaLucia, J., Jr.; Kierzek, R.; Turner, D. H. J. Am. Chem. Soc. 1991, 113, 4313-4322.
(3) Wörner, K.; Strube, T.; Engels, J. W. Helv. Chim. Acta 1999, 82, 2094-2104.
(4) Zagorowska, I.; Adamiak, R. W. Biochemie 1996, 78, 123-130.
(5) Doudna, J. A.; Szostak, J. W.; Rich, A.; Usman, N. J. Org. Chem. 1990, 55, 5547-5549.

2-Aminopurine riboside CEP
Product Details Product Pricing

MF: C50H68N7O8PSi

MW: 954.18

CAS NO: 151059-65-3

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)-β-D-ribofuranosyl]-2-
isobutyrylamino-9H-purine

Alternate Name: 

2-AP CEP
Unit Weight Unit Price Quantity
100 µmol $305.00
0.25 g $775.00
 
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