title: In vitro biosynthesis of unnatural enterocin and wailupemycin polyketides.
abstract: Nature has evolved finely tuned strategies to synthesize rare and complex natural products such as the enterocin family of polyketides from the marine bacterium Streptomyces maritimus. Herein we report the directed ex vivo multienzyme syntheses of 24 unnatural 5-deoxyenterocin and wailupemycin F and G analogues, 18 of which are new. We have generated molecular diversity by priming the enterocin biosynthesis enzymes with unnatural substrates and have illustrated further the uniqueness of this type II polyketide synthase by way of exploiting its unusual starter unit biosynthesis pathways.
authors.affiliation: Scripps Institution of Oceanography and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California at San Diego, La Jolla, California 92093-0204, USA.
authors.forename: John A
authors.initials: JA
authors.lastname: Kalaitzis
authors.forename: Qian
authors.initials: Q
authors.lastname: Cheng
authors.forename: Paul M
authors.initials: PM
authors.lastname: Thomas
authors.forename: Neil L
authors.initials: NL
authors.lastname: Kelleher
authors.forename: Bradley S
authors.initials: BS
authors.lastname: Moore
mesh_terms: D001952:Bridged-Ring Compounds / Q000138:chemical synthesis / Q000737:chemistry; D008386:Marine Biology; D015394:Molecular Structure; D009097:Multienzyme Complexes / Q000378:metabolism*; D048630:Polyketide Synthases / Q000378:metabolism*; D011753:Pyrones / Q000378:metabolism*; D013302:Streptomyces / Q000737:chemistry* / Q000378:metabolism
chemical_list: D001952:Bridged-Ring Compounds; D009097:Multienzyme Complexes; D011753:Pyrones; C548766:wailupemycin F; C548767:wailupemycin G; C012306:enterocin; D048630:Polyketide Synthases