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Malioxamycin, a new antibiotic with spheroplast-forming activity. II. Structural elucidation and total synthesis.

Malioxamycin (1) is a new antibiotic produced by Streptomyces lydicus No. 15748. The structure of malioxamycin has been determined by nmr and mass spectra to possess a hydroxamic acid bond between L-valine and D-malic acid. This structure was confirmed by total synthesis of the antibiotic with (R)-aminooxysuccinic acid and the active ester of L-valine.

Anti-Bacterial Agents↗

Mureidomycins A-D, novel peptidylnucleoside antibiotics with spheroplast forming activity. I. Taxonomy, fermentation, isolation and physico-chemical properties.

A strain of actinomycetes identified as Streptomyces flavidovirens produced new antibiotics, mureidomycins (MRD's) A approximately D, specifically active against Pseudomonas aeruginosa. They were isolated from the culture filtrate by successive column chromatographies such as Amberlite XAD-2 and CG-50, Whatman DE-52 and Toyopearl HW-40. They were amphoteric white powders and soluble in methanol and water. Their molecular weights and molecular formulae in parentheses were 840 (C38H48N8O12S), 842 (C38H50N12S), 897 (C40H51N9O13S) and 899 (C40H53N9O13S), respectively. m-Tyrosine and two unknown substances were detected by amino acid analyses as their common constituents. MRD's A and C contained uracil but MRD's B and D dihydrouracil instead of uracil.

Amino Acids↗

Mureidomycins A-D, novel peptidylnucleoside antibiotics with spheroplast forming activity. II. Structural elucidation.

Structures of new antibiotics, mureidomycins (MRD's) A approximately D, were deduced from spectroscopic analyses and degradation studies. Two residues of m-tyrosine, one residue of 2-amino-3-N-methylaminobutyric acid (AMBA) and methionine are present in all components of the complex. Uracil is contained in MRD's A and C, while dihydrouracil in MRD's B and D. Methionine and m-tyrosine are connected through an ureido bond, and uracil or dihydrouracil is linked to AMBA via enamine sugar moiety. In addition, MRD's C and D contain a glycine residue at the N-terminal.

Amino Acids↗