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  • Title: Synthesis and antibacterial activity of alkyl derivatives of the glycopeptide antibiotic A40926 and their amides.
    Author: Maffioli SI, Ciabatti R, Romanò G, Marzorati E, Preobrazhenskaya M, Pavlov A.
    Journal: Bioorg Med Chem Lett; 2005 Aug 15; 15(16):3801-5. PubMed ID: 15993054.
    Abstract:
    New derivatives of the glycopeptide antibiotic A40926 were synthesized and evaluated for antimicrobial activity against VRE. Deacylated A40926 was obtained by microbial transformation of the parent antibiotic with the use of Actinoplanes teichomyceticus ATCC 31121. Regioselective synthesis of alkylated derivatives of Deacyl A40926 was carried out using lipophilic aliphatic and aromatic halides or aldehydes. Further modification of the two carboxylic acids was performed to increase antibiotic activity. Poor antimicrobial activity was observed for the derivatives obtained by lipophilic mono- or dialkylation of the amino groups present on the molecule, while simultaneous condensation of both carboxylic groups, in hydrophobic derivatives, with dibasic amines led to a strong increase in antibiotic activity.
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