title: Macrolactonization to 10-deoxymethynolide catalyzed by the recombinant thioesterase of the picromycin/methymycin polyketide synthase.
abstract: The recombinant thioesterase (TE) domain of the picromycin/methymycin synthase (PICS) catalyzes the macrolactonization of 3, the N-acetylcysteamine thioester of seco-10-deoxymethynolide to generate 10-deoxymethynolide (1) with high efficiency. By contrast, 4, the 7-dihydro derivative of seco-thioester 3, undergoes exclusive hydrolysis by PICS TE to seco-acid 5. The recombinant TE domain of 6-deoxyerythronolide B synthase (DEBS TE) shows the same reaction specificity as PICS TE, but with significantly lower activity.
authors.affiliation: Department of Chemistry, Box H, Brown University, Providence, RI 02912-9108, USA.
authors.forename: Weiguo
authors.initials: W
authors.lastname: He
authors.forename: Jiaquan
authors.initials: J
authors.lastname: Wu
authors.forename: Chaitan
authors.initials: C
authors.lastname: Khosla
authors.forename: David E
authors.initials: DE
authors.lastname: Cane
mesh_terms: D002384:Catalysis; D004950:Esterases / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D018942:Macrolides / Q000737:chemistry*; D008968:Molecular Conformation; D009097:Multienzyme Complexes / Q000737:chemistry*; D011994:Recombinant Proteins / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D007783:Lactones; D018942:Macrolides; D009097:Multienzyme Complexes; D011994:Recombinant Proteins; C008517:methymycin; C079477:10-deoxymethynolide; D004950:Esterases; C003145:picromycin