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Nucleoside und Nucleotide. Teil 15. Synthese von Desoxyribonucleosid‐monophosphaten und ‐triphosphaten mit 2(1 H )‐Pyrimidinon, 2(1 H )‐Pyridinon und 4‐Amino‐2(1 H )‐pyridinon als Basen
Author(s) -
Kohler Peter,
Wachtl Michael,
Tamm Christoph
Publication year - 1980
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19800630842
Subject(s) - chemistry , nucleoside , deoxyribonucleoside , nucleotide , ribonucleoside , stereochemistry , pyrophosphate , dna , biochemistry , rna , enzyme , gene
Nucleosides and Nucleotide. Part 15. Synthesis of Deoxyribonucleoside Monophosphates and Triphosphates with 2(1 H )‐Pyrimidinone, 2(1 H )‐Pyridinone and 4‐Amino‐2(1 H )‐pyridinone as the Bases The phosphorylation of the modified nucleosides 1‐(2′‐deoxy‐β‐ D ‐ribofuranosyl)‐2(1 H )‐pyrimidinone (M d , 4 ), 4‐amino‐1‐(2′‐deoxy‐β‐ D ‐ribofuranosyl)‐2(1 H )‐pyridinone (Z d , 6 ) and the synthesis of 1–2′‐deoxy‐β‐ D ‐ribofuranosyl‐2(1 H )‐pyrimidinone‐5′‐ O ‐triphosphate (pppM d , 1 ), 1‐(2′‐deoxy‐β‐ D ribofuranosyl)‐2(1 H )‐pyridinone‐5′‐ O ‐triphosphate (ppp II d , 2 ), and 4‐amino‐1‐(2′‐deoxy‐β D ‐ribofuranosyl)‐2(1 H )‐pyridinone‐5′‐ O ‐triphosphate (pppZ d , 3 ) are described. The nucleoside‐5′‐monophosphates pM d (5) and pZ d (7) were obtained by selective phosphorylation of M d (4) and Z d (6) , respectively, using phosphorylchloride in triethyl phosphate or in acetonitril. The reaction of pM d (5) p II d (8) or pZ d (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.