title: Chemoenzymatic approaches toward dechloroansamitocin P-3.
abstract: [reaction: see text] The enantioselective total synthesis of proansamitocin, a key biosynthetic intermediate of the highly potent antitumor agent ansamitocin P-3, is described which bears a diene-ene RCM as the key macrocyclization step. Feeding of proansamitocin to an AHBA block mutant Actinosynnema pretiosum (HGF073) yielded ansamitocin P-3 as well as dechloroansamitocin P-3, the latter also being formed upon fermentation in the presence of 3-amino-5-methoxybenzoic acid.
authors: Institut für Organische Chemie, Leibniz Universität Hannover, Schneiderberg 1B, 30167 Hannover, Germany.
authors: Axel
authors: A
authors: Meyer
authors: Marco
authors: M
authors: Brünjes
authors: Florian
authors: F
authors: Taft
authors: Thomas
authors: T
authors: Frenzel
authors: Florenz
authors: F
authors: Sasse
authors: Andreas
authors: A
authors: Kirschning
mesh_terms: D000192:Actinomycetales / Q000201:enzymology*; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D003500:Cyclization; D006801:Humans; D008453:Maytansine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D015394:Molecular Structure
chemical_list: D000970:Antineoplastic Agents; C520239:dechloroansamitocin P-3; C507695:seco-proansamitocin; D008453:Maytansine