title: Facile and Versatile Chemoenzymatic Synthesis of Enterobactin Analogues and Applications in Bacterial Detection.
abstract: Siderophores, such as enterobactin (Ent), are small molecules that can be selectively imported into bacteria along with iron by cognate transporters. Siderophore conjugates are thus a promising strategy for delivering functional reagents into bacteria. In this work, we present an easy-to-perform, one-pot chemoenzymatic synthesis of functionalized monoglucosylated enterobactin (MGE). When functionalized MGE is conjugated to a rhodamine fluorophore, which affords RhB-Glc-Ent, it can selectively label Gram-negative bacteria that utilize Ent, including some E. coli strains and P. aeruginosa. V. cholerae, a bacterium that utilizes linearized Ent, can also be weakly targeted. Moreover, the targeting is effective under iron-limiting but not iron-rich conditions. Our results suggest that the RhB-Glc-Ent probe is sensitive not only to the bacterial strain but also to the iron condition in the environment.
authors: Department of Chemistry, National Taiwan University, No. 1, Sec. 4, Roosevelt Road, Taipei, 10617, Taiwan) (R.O.C.
authors: Albert A
authors: AA
authors: Lee
authors: Department of Chemistry, National Taiwan University, No. 1, Sec. 4, Roosevelt Road, Taipei, 10617, Taiwan) (R.O.C.
authors: Yi-Chen S
authors: YC
authors: Chen
authors: Department of Chemistry & Biochemistry, University of California, Los Angeles, Los Angeles, CA, 90095, USA.
authors: Elisa
authors: E
authors: Ekalestari
authors: Department of Chemistry, National Taiwan University, No. 1, Sec. 4, Roosevelt Road, Taipei, 10617, Taiwan) (R.O.C.
authors: Sheng-Yang
authors: SY
authors: Ho
authors: Department of Chemistry, National Taiwan University, No. 1, Sec. 4, Roosevelt Road, Taipei, 10617, Taiwan) (R.O.C.
authors: Nai-Shu
authors: NS
authors: Hsu
authors: Department of Chemistry, National Taiwan University, No. 1, Sec. 4, Roosevelt Road, Taipei, 10617, Taiwan) (R.O.C.
authors: Tang-Feng
authors: TF
authors: Kuo
authors: Department of Chemistry, National Taiwan University, No. 1, Sec. 4, Roosevelt Road, Taipei, 10617, Taiwan) (R.O.C.. tswang@ntu.edu.tw.
authors: Tsung-Shing Andrew
authors: 0000-0002-4690-3438
authors: TS
authors: Wang
mesh_terms: D001426:Bacterial Proteins / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D004758:Enterobactin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism; D004926:Escherichia coli / Q000302:isolation & purification* / Q000378:metabolism; D005964:Glucosyltransferases / Q000378:metabolism; D006031:Glycosylation; D016695:Glycosyltransferases / Q000378:metabolism; D013058:Mass Spectrometry; D008853:Microscopy; D011550:Pseudomonas aeruginosa / Q000302:isolation & purification* / Q000378:metabolism; D012235:Rhodamines / Q000737:chemistry
chemical_list: D001426:Bacterial Proteins; D012235:Rhodamines; D004758:Enterobactin; D016695:Glycosyltransferases; D005964:Glucosyltransferases; C519503:OleD protein, Streptomyces antibioticus
keywords: bacteria detection; chemoenzymatic synthesis; click chemistry; enterobactin; siderophores