title: Identification of a hotdog fold thioesterase involved in the biosynthesis of menaquinone in Escherichia coli.
abstract: Escherichia coli is used as a model organism for elucidation of menaquinone biosynthesis, for which a hydrolytic step from 1,4-dihydroxy-2-naphthoyl-coenzyme A (DHNA-CoA) to 1,4-dihydroxy-2-naphthoate is still unaccounted for. Recently, a hotdog fold thioesterase has been shown to catalyze this conversion in phylloquinone biosynthesis, suggesting that its closest homolog, YbgC in Escherichia coli, may be the DHNA-CoA thioesterase in menaquinone biosynthesis. However, this possibility is excluded by the involvement of YbgC in the Tol-Pal system and its complete lack of hydrolytic activity toward DHNA-CoA. To identify the hydrolytic enzyme, we have performed an activity-based screen of all nine Escherichia coli hotdog fold thioesterases and found that YdiI possesses a high level of hydrolytic activity toward DHNA-CoA, with high substrate specificity, and that another thioesterase, EntH, from siderophore biosynthesis exhibits a moderate, much lower DHNA-CoA thioesterase activity. Deletion of the ydiI gene from the bacterial genome results in a significant decrease in menaquinone production, which is little affected in ΔybgC and ΔentH mutants. These results support the notion that YdiI is the DHNA-CoA thioesterase involved in the biosynthesis of menaquinone in the model bacterium.
authors.affiliation: Department of Chemistry and State Key Laboratory of Molecular Neuroscience, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China.
authors.forename: Minjiao
authors.initials: M
authors.lastname: Chen
authors.forename: Xinyu
authors.initials: X
authors.lastname: Ma
authors.forename: Xiaolei
authors.initials: X
authors.lastname: Chen
authors.forename: Ming
authors.initials: M
authors.lastname: Jiang
authors.forename: Haigang
authors.initials: H
authors.lastname: Song
authors.forename: Zhihong
authors.initials: Z
authors.lastname: Guo
mesh_terms: D053898:Biosynthetic Pathways / Q000235:genetics*; D004926:Escherichia coli / Q000201:enzymology* / Q000235:genetics / Q000378:metabolism*; D029968:Escherichia coli Proteins / Q000235:genetics / Q000378:metabolism*; D017353:Gene Deletion; D009284:Naphthols / Q000378:metabolism; D013379:Substrate Specificity; D013869:Thiolester Hydrolases / Q000235:genetics / Q000378:metabolism*; D024482:Vitamin K 2 / Q000378:metabolism*
chemical_list: D029968:Escherichia coli Proteins; D009284:Naphthols; D024482:Vitamin K 2; C024023:1,4-dihydroxy-2-naphthoic acid; C582437:1,4-dihydroxy-2-naphthoyl-coenzyme A thioesterase, E coli; C527558:EntH protein, E coli; D013869:Thiolester Hydrolases
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