Synthesis of [1,3,6,7‐15N, 8‐13C] adenine

Identification of 2,4-diamino-6,7-dimethoxyquinoline derivatives as G9a inhibitors

“…Amino furan 8a and its commercially available analogues 8b and 8c were then converted to the corresponding fused-pyrimidinediones 9a–9c following reported reaction conditions. 28 , 29 The desired dichloropyrimidines 10a–10c were obtained by heating 9a–9c to reflux in the presence of phosphoryl chloride, while the commercially available fused pyrimidinediones 9d and 9e were converted to 10d and 10e using pyrophosphoryl chloride 30 and phosphoryl chloride, respectively. Key intermediates 10a–10e were then substituted with 4-amino-1-benzylpiperidine at C-4 to yield 11a–11e which were further heated with a variety of secondary amines to obtain the fully substituted heterocyclic compounds 12–25 ( Table 1 ).…”

Preparation of Flavocoenzyme Isotopologues by Biotransformation of Purines

“…Methods for the synthesis of xanthine and hypoxanthine are very well documented in the literature and enable the preparation of virtually all conceivable single-labeled and multiple-labeled isotopologues from simple isotope-labeled synthones such as cyanide, bromoacetate, ammonia, and/or nitrite that are all commercially available at moderate costs. − Hence, numerous isotopologues of 6 and of riboflavin carrying single or multiple labels in the heterocyclic part of the respective chromophores can now be prepared as desired for specific spectroscopic problems (cf. Tables and ).…”

“…Xanthine isotopologues were obtained by published procedures. − [6- 17 O 1 ]Hypoxanthine and [6- 18 O 1 ]hypoxanthine were obtained from 6-bromopurine as described in the Supporting Information.…”

Chemical Synthesis of 13C and 15N Labeled Nucleosides

“…Exchange of the 6-chlorine with 15 N-NH 3 followed by reduction of the chlorine in position 2, yields [1,3,6,7-15 N, 8- 13 C]adenine (Scheme 4). 52 Purines are in general more susceptible to nucleophilic than to electrophilic attack. In alkaline medium, however nucleophilicity is strongly reduced due to deprotonation of the NH of the imidazole ring.…”