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Characterization of the Two Methylation Steps Involved in the Biosynthesis of Mycinose in Tylosin
- Characterization of the Two Methylation Steps Involved in the Biosynthesis of Mycinose in Tylosin
- Kim, Eunji; Song, Myoung Chong; Kim, Myoun Su; Beom, Ji Yoon; Lee, Eun Yeol; Kim, Dong-Myung; Nam, Sang-Jip; Yoon, Yeo Joon
- Ewha Authors
- 윤여준; 송명종; 남상집
- SCOPUS Author ID
- 윤여준; 송명종; 남상집
- Issue Date
- Journal Title
- JOURNAL OF NATURAL PRODUCTS
- 0163-3864; 1520-6025
- vol. 79, no. 8, pp. 2014 - 2021
- AMER CHEMICAL SOC
- SCI; SCIE; SCOPUS
- The S-adenosyl-L-methionine-dependent O-methyltransferases TylE and TylF catalyze the last two methylation reactions in the tylosin biosynthetic pathway of Streptomyces fradiae. It has long been known that the TylE-catalyzed C2'"-O-methylation of the 6-deoxy-D-allose bound to demethylmacrocin or demethyllactenocin precedes the Ty1F-catalyzed C3"'-O-methylation of the D-javose (C2"'-O-methylated 6-deoxy-D-allose) attached to macrocin or lactenocin. This study reveals the unexpected substrate promiscuity of TylE and TylF responsible for the biosynthesis of D-mycinose (Cr"'-O-methylated D-javose) in tylosin through the identification of a new minor intermediate 2"'-O-demethyldesmycosin (2; 3"'-methyl-demethyllactenocin), which lacks a 2"'-O-methyl group on the mycinose moiety of desmycosin, along with 2"'-O-demethyltylosin (1; 3"'-methyl-demethylmacrocin) that was previously detected from the S. fradiae mutant containing a mutation in the tylE gene. These results unveil the unique substrate flexibility of TylE and TylF and demonstrate their potential for the engineered biosynthesis of novel glycosylated macrolide derivatives.
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