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Nucleoside und Nucleotide. Teil 16. Verhalten von 1‐(2′‐Desoxy‐β‐ D ‐ribofuranosyl)‐2(1 H )‐pyrimidinon‐5′‐triphosphat, 1‐(2′‐Desoxy‐β‐ D ‐ribofuranosyl)‐2(1 H )pyridinon‐5′‐triphosphat und 4‐Amino‐1‐(2′‐Desoxy‐β‐ D ‐ribofuranosyl)‐2(1 H )‐pyridinon‐5′‐triphosphat gegenüber DNA‐Polymerase
Author(s) -
Wachtl Michael,
Kohler Peter,
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.19800630843
Subject(s) - chemistry , nucleotide , dna polymerase , ribonucleoside , nucleoside , polymerase , stereochemistry , guanine , base pair , nucleoside triphosphate , nucleoside diphosphate kinase , dna , microbiology and biotechnology , biochemistry , enzyme , rna , biology , gene
Nucleosides and Nucleotides. Part 16. The Behaviour of 1‐(2′‐Deoxy‐β‐ D ‐ribofuranosyl)‐2(1 H )‐pyrimidinone‐5′‐triphosphate, 1‐(2′‐Deoxy‐β‐ D ‐ribofuranosyl‐2(1 H ))‐pyridinone‐5′‐triphosphate and 4‐Amino‐1‐(2′‐desoxy‐β‐ D ‐ribofuranosyl)‐2(1 H )‐pyridinone‐5′‐triphosphate towards DNA Polymerase The behaviour of nucleotide base analogs in the DNA synthesis in vitro was studied. The investigated nucleoside‐5′‐triphosphates 1‐(2′‐deoxy‐β‐ D ‐ribofuranosyl)‐2(1 H )‐pyrimidinone‐5′‐triphosphate (pppM d ), 1‐(2′‐deoxy‐β‐ D ‐ribofuranosyl)‐2(1 H )‐pyridinone‐5′‐triphosphate (ppp II d ) and 4‐amino‐1‐(2′‐deoxy‐β‐ D ‐ribofuranosyl)‐2(1 H )‐pyridinone‐5′‐triphosphate (pppZ d ) can be considered to be analogs of 2′‐deoxy‐cytidine‐5′‐triphosphate. However, their ability to undergo base pairing to the complementary guanine is decreased. When pppM d , ppp II d or pppZ d are substituted for pppC d in the enzymatic synthesis of DNA by DNA polymerase no incorporation of these analogs is observed. They exhibit only a weak inhibition of the DNA synthesis. The mode of the inhibition is uncompetitive which shows that these nucleotide analogs cannot serve as substrates for the DNA polymerase.