L-Chlorozotocin.
L-Chlorozotocin (2-[[[2-chloroethyl)nitrosoamino]carbonyl]amino]-2-deoxy-L-glucose) was synthesized in seven steps from L-arabinose for comparison with chlorozotocin, which is the D enantiomorph and an antineoplastic agent with clinical potential. Purification of the intermediate 2-amino-2-deoxy-L-glucose as the Schiff's base formed with 4-methoxybenzaldehyde ensured complete separation from the manno epimer. Comparative screening against leukemia L1210 with concurrent toxicity controls revealed no significant difference between D- and L-chlorozotocin in either activity or toxicity.
D000818:Animals; D001853:Bone Marrow / Q000187:drug effects / Q000378:metabolism; D004273:DNA, Neoplasm / Q000096:biosynthesis; D007939:Leukemia L1210 / Q000188:drug therapy / Q000378:metabolism; D008297:Male; D051379:Mice; D013237:Stereoisomerism; D013311:Streptozocin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
D004273:DNA, Neoplasm; C007028:chlorozotocin; D013311:Streptozocin