Oxamycin

Oxamide [471-46-5] M 88.1, m >320°(dec). Crystd from water, ground and dried in an oven at 150°. Oxamycin see 77-4-amino-3-isoxazolidone. 

Another enzyme-activated inhibitor is the streptomyces antibiotic D-cycloserine (oxamycin), an antitubercular drug that resembles D-alanine in structure. A potent inhibitor of alanine racemase, it also inhibits die non-PLP, ATP-dependent, D-alanyl-D-alanine synthetase which is needed in the biosynthesis of die peptidoglycan of bacterial cell walls. 

D-4-Amino-3-isoxzolidinone Orientomycin cRosina Farmiserina Micoserina Oxamycin ... 

A few antibiotics that are produced by Streptomyces spp. have structural affinities to single amino acids. Thus D-cycloserine (oxamycin), which has the structure XXVIII, could formally be obtained from D-serine amide by removal of the elements of water, or from D-alanine by an oxidative process. 

The introduction of penicillin into medical practice in 1941, and of streptomycin, chloramphenicol, and the tetracyclines in the following 8 years, opened up a new vista in chemotherapy. Antibiotics were at first regarded with much awe, and a completely new mode of action was predicted for them. In the course of time, though, they have been found to use the established types of receptor. Those antibiotics like penicillin and cephalosporin which prevent the synthesis of bacterial cell-wall have turned out to have an enzyme for receptor (Section 12.i), and this is true of the simpler oxamycin (Section 9.4). Many other antibiotics act on DNA, preventing its replication or transcription such are adriamycin, actinomycin, mitomycin, and bleomycin (Section 4.0). Rifamycin, however, acts on the protein of DNA-primed RNA-polymerase. 

The above two antibiotics, quite unlike penicillin and oxamycin, also slowly increase the permeability of the cytoplasmic membrane (Reynolds, 1966). The need of bacitracin for a divalent metal, mentioned in Section 11.9, is apparently connected with this secondary site of attack. 

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