Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Journal of Antibiotics called Malioxamycin, a new antibiotic with spheroplast-forming activity. II. Structural elucidation and total synthesis, Author is Takahashi, Shuji; Takeuchi, Michiko; Inukai, Masatoshi; Arai, Mamoru, which mentions a compound: 20859-23-8, SMILESS is O=C(O)[C@@H](Br)CC(O)=O, Molecular C4H5BrO4, Name: (S)-2-Bromosuccinic acid.
The structure of malioxamycin was determined to be H-L-Val-(R)-NHOCH(CO2H)CH2CO2H (I) by NMR and mass spectrometry. The structure of I was confirmed by stereospecific total synthesis. Thus, (S)-HO2CCH2CHBrCO2H underwent a substitution reaction with BzNHOH in EtOH containing NaOEt with an inversion of configuration to give (R)-HO2CCH2CH(ONHBz)CO2H, which was cleaved by HOAc/HCl to give (R)-HO2CHCH(ONH2)CO2H. The latter was coupled to Z-L-Val-ONSu (Z = PhCH2O2C, NSu = succinimido) to give the protected malioxymycin, which was Z-deblocked by hydrogenolysis to give I.
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Reference:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”