Deoxyadenylyl deoxyadenosine

Receptor models 71a and 71b for dinucleotides (dinucleoside monophosphates) have been developed out of 69 by replacing the naphthoyl residue, which is not involved in any host-guest interactions in the complexes, by a second carbazolyl cleft. The adenine selectivity of the two pincers was reflected in single extraction experiments dissolved in CH2CI2,71a removes one full equivalent of both adenylyl(3 -+ 5 )adenosine (ApA) and 2 -deoxyadenylyl(3 ->5 )-2 -deoxyadenosine [d(ApA)] 72 out of aqueous solutions of guest (8-fold excess) but only half the amount of d(ApG) [103]. 

Deoxo-9-metboxyiniinoerythromycin, E-18 Deoxorubicinol, A-58 18-Deoxospiramycin I, F-24 2 -Deoxy-5 -adenylic acid, D-28 3 -Deoxyadenosine, C-152 2 -Deoxyadenosine, D-28 5 -Deoxyadenosine, D-29 5 -Deoxy-5 -adenosineacetic acid, D-30 2 -Deoxy-3 -adenylic acid, D-28 2 -Deoxyadenylyl-(3" 50-2 -deoxyguanosine, D-31 Deoxyadriamycinone, A-58 6-Deoxy-D-allal, D-679... 

Ikehara, M., Takatsuka, Y., and Uesugi, S (1979) Polynucleotides LIII. Synthesis and properties of 2 -azido-2 -deoxyadenylyl-(3 -5 )-2 -azido-2 deoxyadenosine. Chem. Pharm. Bull. 27, 1830-1835,... 

No isomerization of ApA to adenylyl(2 -5 )adenosine has been observed. The absence of Co " complex-catalyzed hydrolysis of 2 -deoxyadenylyl(3 -5 )2 -deoxyadenosine is considered to be indirect evidence for the intramolecular nucleophilic attack by the 2 -OH of ribose toward the phosphodiester linkage in the hydrolysis of RNA. The proposed mechanism for Co "-complex-catalyzed hydrolysis of ApA as described by Equation 2.37 is similar to Scheme 2.24, except that Scheme 2.24 does not involve the pentacoordinated intermediate similar to PI in Equation 2.37. 

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