US EPA

7501889 

Journal Article 

Synthesis of Naturally Occurring 6-Ureidopurines and Their Nucleosides1 

Chheda, GB; Hong, CL 

1971 

Yes 

Journal of Medicinal Chemistry
ISSN: 0022-2623
EISSN: 1520-4804 

14 

8 

748-753 

English 

10.1021/jm00290a019 

The naturally occurring modified purines, N-(purin-6-ylcarbamoyl)threonine (PCT, I) and N-(purin-6-ylcarbamoyl)glycine (PCG, IV), and their ribosides, PCTR (II) and PCGR (III), have been synthesized. Facile syntheses of the key intermediates, ethyl purine-6-carbamate (VI) and its riboside (XI), weee achieved by new methods. Displacement of the EtO group of urethanes VI and XI with L-threonine and glycine gave PCT (I), PCTR (II), PCG (IV), and PCGR (III). Compounds I and II weee also prepared through reaction of 2',3',5'-tri-O-acetyladenosine with a suitably blocked threonine isocyanate, followed b}r deblocking. These synthetic studies confirm the earlier suggestion that the threonine of natural compound I has the l configuration. © 1971, American Chemical Society. All rights reserved. 

cyanic acid derivative; nucleoside; purine derivative; threonine; urethan; acute granulocytic leukemia; article; bioassay; cell line; chemistry; human; metabolism; paper chromatography; spectroscopy; stimulation; synthesis; ultraviolet radiation; Biological Assay; Cell Line; Chemistry; Chromatography, Paper; Cyanates; Human; Leukemia, Myelocytic, Acute; Nucleosides; Purines; Spectrum Analysis; Stimulation, Chemical; Threonine; Ultraviolet Rays; Urethane