title: Synthesis of a cytotoxic ansamycin hybrid.
abstract: The synthesis of a new ansamycin macrolactam derivative that contains an ansa chain based on ansamitocin and an aromatic core related to geldanamycin is reported. The selective introduction of the cyclic carbamoyl group at C7 and C9 relies on a biotransformation using a mutant strain of S. hygroscopicus, the geldanamycin producer. The ansamycin hybrid forms atropisomers that differ in their antiproliferative activity toward cancer cells.
authors.affiliation: Institute of Organic Chemistry and Center of Biomolecuclar Drug Research (BMWZ), Leibniz Universität Hannover , Schneiderberg 1B, 30167 Hannover, Germany.
authors.forename: Gerrit
authors.initials: G
authors.lastname: Jürjens
authors.forename: Andreas
authors.initials: A
authors.lastname: Kirschning
mesh_terms: D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D016227:Benzoquinones / Q000737:chemistry*; D045744:Cell Line, Tumor; D006801:Humans; D047029:Lactams, Macrocyclic / Q000737:chemistry*; D015394:Molecular Structure; D017828:Rifabutin / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D013302:Streptomyces / Q000737:chemistry* / Q000378:metabolism
chemical_list: D000903:Antibiotics, Antineoplastic; D016227:Benzoquinones; D047029:Lactams, Macrocyclic; D017828:Rifabutin; C001277:geldanamycin