title: Azido Pentoses: A New Tool To Efficiently Label Mycobacterium tuberculosis Clinical Isolates.
abstract: Mycobacterium tuberculosis (Mtb), the main causative agent of tuberculosis (Tb), has a complex cell envelope which forms an efficient barrier to antibiotics, thus contributing to the challenges of anti-tuberculosis therapy. However, the unique Mtb cell wall can be considered an advantage and be utilized to selectively label Mtb bacteria. Here we introduce three azido pentoses as new compounds for metabolic labeling of Mtb: 3-azido arabinose (3AraAz), 3-azido ribose (3RiboAz), and 5-azido arabinofuranose (5AraAz). 5AraAz demonstrated the highest level of Mtb labeling and was efficiently incorporated into the Mtb cell wall. All three azido pentoses can be easily used to label a variety of Mtb clinical isolates without influencing Mtb-dependent phagosomal maturation arrest in infection studies with human macrophages. Thus, this metabolic labeling method offers the opportunity to attach desired molecules to the surface of Mtb bacteria in order to facilitate investigation of the varying virulence characteristics of different Mtb clinical isolates, which influence the outcome of a Tb infection.
authors.affiliation: Otto Diels Institute of Organic Chemistry, Christiana Albertina University of Kiel, Otto-Hahn-Platz 3-4, 24118, Kiel, Germany.|Microbial Interface Biology, Research Center Borstel, Leibniz Center for Medicine and Biosciences, Parkallee 22, 23845, Borstel, Germany.|Present address: Tuberculosis Research Section, NIAID, NIH, 33 North Drive, Bethesda, MD, 20814, USA.
authors.forename: Katharina
authors.initials: K
authors.lastname: Kolbe
authors.affiliation: Department of Physical Chemistry, Ludwig Maximilian University of Munich, Butenandstrasse 11, 81377, Munich, Germany.
authors.forename: Leonhard
authors.initials: L
authors.lastname: Möckl
authors.affiliation: Microbial Interface Biology, Research Center Borstel, Leibniz Center for Medicine and Biosciences, Parkallee 22, 23845, Borstel, Germany.
authors.forename: Victoria
authors.initials: V
authors.lastname: Sohst
authors.affiliation: Microbial Interface Biology, Research Center Borstel, Leibniz Center for Medicine and Biosciences, Parkallee 22, 23845, Borstel, Germany.
authors.forename: Julius
authors.initials: J
authors.lastname: Brandenburg
authors.affiliation: Structural Biochemistry, Research Center Borstel, Leibniz Center for Medicine and Biosciences, Parkallee 4, 23845, Borstel, Germany.
authors.forename: Regina
authors.initials: R
authors.lastname: Engel
authors.affiliation: Molecular and Experimental Mycobacteriology, Research Center Borstel, Leibniz Center for Medicine and Biosciences, Parkallee 22, 23845, Borstel, Germany.
authors.forename: Sven
authors.initials: S
authors.lastname: Malm
authors.affiliation: Department of Physical Chemistry, Ludwig Maximilian University of Munich, Butenandstrasse 11, 81377, Munich, Germany.
authors.forename: Christoph
authors.initials: C
authors.lastname: Bräuchle
authors.affiliation: Structural Biochemistry, Research Center Borstel, Leibniz Center for Medicine and Biosciences, Parkallee 4, 23845, Borstel, Germany.
authors.forename: Otto
authors.initials: O
authors.lastname: Holst
authors.affiliation: Otto Diels Institute of Organic Chemistry, Christiana Albertina University of Kiel, Otto-Hahn-Platz 3-4, 24118, Kiel, Germany.
authors.forename: Thisbe K
authors.initials: TK
authors.lastname: Lindhorst
authors.affiliation: Microbial Interface Biology, Research Center Borstel, Leibniz Center for Medicine and Biosciences, Parkallee 22, 23845, Borstel, Germany.|German Center for Infection Research (DZIF), Partner Site Hamburg-Lübeck-Borstel, Parkallee 1-40, 23845, Borstel, Germany.
authors.forename: Norbert
authors.initials: N
authors.lastname: Reiling
mesh_terms: D001386:Azides / Q000737:chemistry*; D015415:Biomarkers / Q000378:metabolism; D002473:Cell Wall / Q000737:chemistry* / Q000378:metabolism; D005434:Flow Cytometry; D015870:Gene Expression; D006801:Humans; D051907:Lysosomal Membrane Proteins / Q000235:genetics / Q000276:immunology; D008264:Macrophages / Q000166:cytology / Q000276:immunology; D009169:Mycobacterium tuberculosis / Q000737:chemistry* / Q000378:metabolism; D010429:Pentoses / Q000737:chemistry*; D010587:Phagocytosis; D013194:Staining and Labeling / Q000379:methods*; D020696:rab5 GTP-Binding Proteins / Q000235:genetics / Q000276:immunology; D052118:Lysosomal-Associated Membrane Protein 1
chemical_list: D001386:Azides; D015415:Biomarkers; D051907:Lysosomal Membrane Proteins; D010429:Pentoses; D020696:rab5 GTP-Binding Proteins; C489116:LAMP1 protein, human; D052118:Lysosomal-Associated Membrane Protein 1; C427755:RAB5C protein, human
keywords: Mycobacterium tuberculosis; arabinan metabolism; carbohydrates; click chemistry; metabolic labeling