L-Alanosine

Alston TA, Bright HJ. 1982. Enzymatic release of nitric oxide from L-alanosine, an antineoplastic antibiotic. Biochem. Bio-phys. Res. Commun. 105 560-66... 

L Alanosine, 3-(,Mydroxyrtitmftoam no)-v-alan ne L-2-amino-3-(hydroxynitrosoaminfnpropano tc acid L-2-amino-3-[(N-nitroso)hydroxylaimno]propionic acid. CjH7-N304 mol wt 149.11- C 24-16%, H 4.73%, N 28.18%, O 42 92%. Antibiotic substance from ihe fermentation of Streptomyces alanosinicus n. sp. Prepn Neth. pat, Appl. 

Webster, H. K., Whaun, J. M., Walker, M. D., and Bean, T. L. (1984a). Synthesis of adenosine nucleotides from hypoxanthine by human malaria parasites (Plasmodium falciparum) in continuous erythrocyte culture Inhibition by hadacidin but not alanosine. Biochem. Pharmacol. 33,1555-1557. 

Lancini, G.C., A. Diena, and E. Lazzari The Synthesis of Alanosine [L-2-Amino-3-(N-nitrosohydroxylamino)propionic Acid]. Tetrahedron Letters 1966, 1769. 

Alanosine (L-2-amino-3-(N-hydroxy, N-nitrosamino) propionic acid), another inhibitor of adenylosuccinate synthetase (7), did not appear to interfere with synthesis of adenosine nucleotides by malaria infected erythrocytes (Table 1). There was, however, an unexpected decrease in labelled GTP and total guanylates (EG). 

Hadacidin, bredinin and mycophenolic acid, each shown to effect specific purine enzymes in other types of cells acted predictably to disrupt purine nucleotide synthesis by PRBC. The lack of a detectable effect on adenylate synthesis by alanosine may be due to an inability to form the active metabolite, L-alanosyl-AICOR, which requires an active de novo purine pathway (10). 

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