31. SYNTHESIS OF POLYNUCLEOTIDES 



Example 3 



109 



Structure 



Diagrammatic representation Abbreviation 



HOCH, 



Cytosine 



O OH 



/ 

 HO— P=0 



OCH 2 



o 



Adenine 



O OH 



HO— P=0 



OCHo /"°- 



Uracil 



U 



P CpApU-Cyclic p 



O O 



\ / 

 P 



/ % 

 HO O 



Full name: Cytidylyl-(3' — -> 5')-adenylyl-(3' — + 5')-uridine-2',3' cyclic phosphate 



1. Methods for the Synthesis of Internucleotide 

 (Phosphodiester) Bonds 



a. The Use of Bifunctional Phosphor ylating Agents 



The reagent monophenylphosphorodichloridate (I) has been used by 



O 



II / = \ 



ROP— CI (I), P 



CI 



(II), R = 2 N 



vj- 



Baer 9 and his colleagues in their extensive synthetic work in the phospho- 

 lipid field and involves the successive phosphorylations of two different hy- 

 droxylic compounds as shown below. 



9 E. Baer, Can. J. Biochem. Physiol. 34, 288 (1955). 



