Macrolactonization to 10-deoxymethynolide catalyzed by the recombinant thioesterase of the picromycin/methymycin polyketide synthase.
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.
He
Weiguo
W
Department of Chemistry, Box H, Brown University, Providence, RI 02912-9108, USA.
Wu
Jiaquan
J
Khosla
Chaitan
C
Cane
David E
DE
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
D007783:Lactones; D018942:Macrolides; D009097:Multienzyme Complexes; D011994:Recombinant Proteins; C008517:methymycin; C079477:10-deoxymethynolide; D004950:Esterases; C003145:picromycin