Sulfonate analogues of adenosine nucleotides as inhibitors of nucleotide-binding enzymes.
2-(Adenin-9-yl)ethanesulfonic acid (1), 3-(adenin-9-yl)propanesulfonic acid (2), 9-(5-deoxy-beta-D-ribofuranosyl)-adenine-5'-sulfonic acid (3), and 9-(3-deoxy-beta-D-arabinofuranosyl)adenine-3'-sulfonic acid (4) were prepared by reaction of the corresponding chlorides by sodium sulfite (1-3) or by reaction of an epoxide with sodium hydrogen sulfite (4). They inhibited a typical nucleotide-binding enzyme, horse liver alcohol dehydrogenase, with inhibition constants in the range of 0.18-4.9 mM at pH 8, 25 degrees C.
D000227:Adenine Nucleotides / Q000138:chemical synthesis* / Q000494:pharmacology; D000429:Alcohol Oxidoreductases / Q000037:antagonists & inhibitors*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D013451:Sulfonic Acids / Q000138:chemical synthesis* / Q000494:pharmacology
D000227:Adenine Nucleotides; D004791:Enzyme Inhibitors; D013451:Sulfonic Acids; D000429:Alcohol Oxidoreductases