A new method for the synthesis of dinucleotides

✍ Scribed by Tsujiaki Hata; Iwao Nakagawa; Noriyori Takebayashi

• Publisher: Elsevier Science
• Year: 1972
• Tongue: French
• Weight: 166 KB
• Volume: 13
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)84975-3

✦ Synopsis

An attempt to prepare oligonucleotides by the use of a protecting group which acts as a purification handle for separation has been investigated in our laboratory. 2)

We now wish to report a new synthetic method for dinucleotides containing 2'-deoxyadenosine and thymidine nucleotides. 3-(N,N-Diethylaminomethyl)anilino group (N) was chosen as a protecting group on the 2'-deoxyribonucleoside 5'-phosphate end. This group was introduced to form a phosphoroanilidate linkage starting from N,N-diethyl-3-aminobensyl amine and the corresponding nucleoside 5'-phosphate by means of Mukaiyama's reagent. 3) This phosphoroanilidate linkage was found to be cleaved easily by treatment with isoamylnitrite according to Ikehara's method.4) Both of the 5'-phosphoroanilidate derivatives of NC-bensoyl 2'-deoxyadenosine (d-NpABZ) and thymidine (d-NpT) were obtained in 80% and 86% yields, respectively. 5) The phosphoroanilidates in the form of their inner salts are neutral and very stable substances and were easily isolated and purified from the reaction mixture by washing with ether and further by using DEAE cellulose (carbonate form) column chromatography.