title: Bioreduction of aryl azides during mutasynthesis of new ansamitocins.
abstract: Supplementing a culture of a mutant strain of Actinosynnema pretiosum that is unable to biosynthesize aminohydroxy benzoic acid (AHBA), with 3-azido-5-hydroxy-benzoic acid and 3-azido-5-amino-benzoic acid, unexpectedly yielded anilino ansamitocins instead of the expected azido derivatives. This is the first example of the bioreduction of organic azides. The unique nature of these results was demonstrated when 3-azido-5-amino-benzoic acid was fed to the corresponding AHBA blocked mutant of Streptomyces hygroscopicus, the geldanamycin producer. This mutasynthetic experiment yielded the fully processed azido derivative of geldanamycin.
authors: Institut für Organische Chemie und Biomolekulares Wikstoffzentrum (BMWZ) der Leibniz Universität Hannover, Schneiderberg 1B, 30167 Hannover, Germany.
authors: Lena
authors: L
authors: Mancuso
authors: Gerrit
authors: G
authors: Jürjens
authors: Jekaterina
authors: J
authors: Hermane
authors: Kirsten
authors: K
authors: Harmrolfs
authors: Simone
authors: S
authors: Eichner
authors: Jörg
authors: J
authors: Fohrer
authors: Wera
authors: W
authors: Collisi
authors: Florenz
authors: F
authors: Sasse
authors: Andreas
authors: A
authors: Kirschning
mesh_terms: D062365:Aminobenzoates / Q000737:chemistry / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001386:Azides / Q000737:chemistry* / Q000494:pharmacology; D016227:Benzoquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D062385:Hydroxybenzoates / Q000737:chemistry / Q000494:pharmacology*; D047029:Lactams, Macrocyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008453:Maytansine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D013302:Streptomyces / Q000737:chemistry* / Q000235:genetics / Q000378:metabolism
chemical_list: D062365:Aminobenzoates; D000900:Anti-Bacterial Agents; D001386:Azides; D016227:Benzoquinones; D062385:Hydroxybenzoates; D047029:Lactams, Macrocyclic; D008453:Maytansine; C015682:ansamitocins; C031509:3-amino-5-hydroxybenzoic acid; C001277:geldanamycin