Nucleoside und Nucleotide. Teil 15. Synthese von Desoxyribonucleosid-monophosphaten und -triphosphaten mit 2(1H)-Pyrimidinon, 2(1H)-Pyridinon und 4-Amino-2(1H)-pyridinon als Basen

✍ Scribed by Peter Kohler; Michael Wachtl; Christoph Tamm

• Publisher: John Wiley and Sons
• Year: 1980
• Tongue: German
• Weight: 446 KB
• Volume: 63
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19800630842

✦ Synopsis

~~ Nucleosides and Nucleotides. Part 15. Synthesis of Deoxyrihonucleoside Monophosphates and Triphosphates with 2(1 H)-Pyrimidinone, 2(1H)-Pyridinone and 4-Amino-2(1 H)-pyridinone as the Bases Summary The phosphorylation of the modified nucleosides 1-(2'-deoxy-f3-~-ribofurano-sy1)-2( 1 H)-pyrimidinone (M,, 4), 4-amino-1 -(2'-deoxy-p-~-ribofuranosyl)-2( 1 H )pyridinone (Z,, 6) and the synthesis of 1-(2'-deoxy-~-~-ribofuranosy1)-2( 1 H)-pyrimidinone-5'-O-triphosphate (pppM,, l), 1-(2'-deoxy-fi-~-ribofuranosy1)-2( 1 H )pyridinone-5'-O-triphosphate (pppnd, 2), and 4-amino-l-(2'-deoxy-~-~-ribofurano-sy1)-2( 1 H)-pyridinone-5'-O-triphosphate (pppzd, 3) are described. The nucleoside-5'-monophosphates pM, ( 5 ) and pZ, (7) were obtained by selective phosphorylation of M, (4) and z d (6), respectively, using phosphorylchloride in triethyl phosphate or in acetonitril. The reaction of pM, (5), pnd (8) or pZ, (7) with morpholine in the presence of DCC led to the phosphoric amides 9, 10 and 11, respectively, which were converted with tributylammonium pyrophosphate in dried dimethylsulfoxide to the nucleoside-5'triphosphates 1, 2 and 3, respectively. 1. Einleitung. ~ Im Rahmen unserer Untersuchungen uber die DNA-bzw. RNA-Polymerasenspezifitat mit Hilfe von Nucleotiden, deren Base nur beschrankt Whig ist, Wasserstoffbrucken zu naturlichen Nucleotiden auszubilden, haben wir die Synthese von 1 -(2'-Desoxy-P-~-ribofuranosyl)-2( 1 H)-pyrimidinon-5'-O-triphosphat (pppM,, 14)) 1-(2'-Desoxy-fi-~-ribofuranosyl)-2(1 H)-pyrimidinon-5'-O-triphosphat (pppnd ,2)und4-Amino-1-(2'-desoxy-~-~-ribofuranosyl)-2( 1 H)-pyridinon-5'-triphosphat (pppzd, 3) durchgefuhrt. Anschliessend wurde das Verhalten dieser Verbindungen gegenuber der DNA-Polymerase untersucht [5]. I ) Teil 14 s. [I]. ') 3 , Korrespondenz-Autor. ") Zu den Abkurzungen vgl. [4]. M, = l-(2'-Desoxy-~-~-ribofuranosyl)-2(1 H)-pyrimidinon, nd = l-(2'-Desoxy-~-~-ribofuranosyl)-2(1 H)-pyridinon und Z, = 4-Amino-l-(2'-desoxy-jj-~-ribofuranosyl)-2 (1 H)-pyridinon. Fur Einzelheiten vgl. [2] [ 3 ] .