Max Tishler

Structure of prumycin

The antibiotic prumycin has been identified as 4-D-alanylamino-2-amino-2,4-dideoxy-L-arabinose (1). 1H and 13C N.m.r. data for prumycin and related compounds, particularly the methyl glycoside of O-acetyl-NN′-bisbenzyl-oxycarbonylprumycin (6β) and NN′-diacetylprumycin (3), were major factors in establishing the structure. The absolute configuration was derived by comparing the optical rotation of prumycin with those of other L-arabinose derivatives.

THE SYNTHESIS AND BIOLOGICAL ACTIVITY OF S-ALKYL PHOSPHOHOMOCYSTEINE SULFOXIMIDES

Abstract The phosphonate analogues of methionine and buthionine sulfoximide were synthesized by the action of NaN3 on the corresponding sulfoxides. Analogues 3 and 4 were prepared to determine the effect of altering the carboxyl portion of known inhibitors in the glutamate synthase cycle. Results of biological testing revealed that 3 and 4 did not posses the potency found with buthionine and methionine sulfoximide in cellular systems. However 3 was found to be an effective and irreversible inhibitor of glutamine synthetase.