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This realization has inspired many attempts to search for novel methyltransferases. Chalcomycins are a group of 16\u2010membered macrolides containing two methylated sugars that require three methyltransferases for their biosynthesis. Here, we identified that AlmCII, a sugar O\u2010methyltransferase belonging to the TylF family that was previously only known to methylate sugars with a 4\u2032\u2010hydroxy group, can methylate a 4\u2032,6\u2032\u2010dideoxysugar during the biosynthesis of chalcomycins. An in vitro enzymatic assay revealed that AlmCII is divalent metal\u2010dependent with an optimal pH of 8.0 and optimal temperature of 42\u2009\u00b0C. Moreover, the 3\u2032\u2010O\u2010demethylated chalcomycins exhibit less than 6\u2009% of the antibacterial activity of their parent compounds. This is the first report demonstrating that a TylF family O\u2010methyltransferase can use a 4\u2032\u2010deoxy sugar as a substrate and highlighting the importance of this methylation for the antibacterial activity of chalcomycins.<\/jats:p>","DOI":"10.1002\/cbic.201700216","type":"journal-article","created":{"date-parts":[[2017,5,10]],"date-time":"2017-05-10T07:58:50Z","timestamp":1494403130000},"page":"1510-1517","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Characterization of Methyltransferase AlmCII in Chalcomycin Biosynthesis: The First TylF Family O\u2010Methyltransferase Works on a 4\u2032\u2010Deoxysugar"],"prefix":"10.1002","volume":"18","author":[{"given":"Ping","family":"Dai","sequence":"first","affiliation":[{"name":"Institute of Traditional Chinese Medicine and Natural Products College of Pharmacy Jinan University  No. 601 Huangpu Avenue Guangzhou 510632 P. R. 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