Аланозин

Crystalline Powder

Antibiotic substance from the fermentation of Streptomyces alanosinicus. The first natural product found to have a N-nitrosohydroxylamino group on an aliphatic chain. An experimental insect reproduction inhibitor

This antibiotic and aspartate/asparagine analogue (FW = 149.11 g/mol; CAS 5854-93-3), also named L-2-amino-3-(N-hydroxy-N-nitrosoamino) propionic acid, isolated from fermentation broths of Streptomyces alanosinicus, inhibits adenylosuccinate synthetase, disrupting de novo synthesis of AMP in both malignant and normal cells. That alanosine inhibits the adenylosuccinate synthetase reaction, the first step in the conversion of IMP to AMP, is evidenced by the accumulation of IMP, but not adenylosuccinate, in treated cells. L-Alanosine’s action is potentiated in methylthioadenosine phosphorylase (MTAP) deficiency. Clinical use is limited by its toxicity. At a concentration as low as 2.7 μM, L-alanosine completely inhibits the incorporation of hypoxanthine into adenosine triphosphate by cultured Novikoff rat hepatoma cells. A related agent, L-alanosyl-5-aminoimidazole-4-carboxylic acid ribonucleotide (or alanosyl-AICOR) has been synthesized enzymatically using 4-(N-succino)- 5-aminoimidazole-4-carboxamide ribonucleotide (or SAICAR) synthetase in conjunction with 5-aminoimidazole-4-carboxylic acid ribonucleotide and alanosine. Alanosyl-AICOR is not a substrate of adenylosuccinate lyase from rat skeletal muscle, but it was an apparent competitive inhibitor in both reactions catalyzed by the enzyme.