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Characterization of the Two Methylation Steps Involved in the Biosynthesis of Mycinose in Tylosin

Title
Characterization of the Two Methylation Steps Involved in the Biosynthesis of Mycinose in Tylosin
Authors
Kim, EunjiSong, Myoung ChongKim, Myoun SuBeom, Ji YoonLee, Eun YeolKim, Dong-MyungNam, Sang-JipYoon, Yeo Joon
Ewha Authors
윤여준송명종남상집
SCOPUS Author ID
윤여준scopus; 송명종scopus; 남상집scopus
Issue Date
2016
Journal Title
JOURNAL OF NATURAL PRODUCTS
ISSN
0163-3864JCR Link1520-6025JCR Link
Citation
vol. 79, no. 8, pp. 2014 - 2021
Publisher
AMER CHEMICAL SOC
Indexed
SCI; SCIE; SCOPUS WOS scopus
Abstract
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.
DOI
10.1021/acs.jnatprod.6b00267
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자연과학대학 > 화학·나노과학전공 > Journal papers
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