2. Academic Validation
  3. Full color palette of fluorescent d-amino acids for in situ labeling of bacterial cell walls

Full color palette of fluorescent d-amino acids for in situ labeling of bacterial cell walls

  • Chem Sci. 2017 Sep 1;8(9):6313-6321. doi: 10.1039/c7sc01800b.
Yen-Pang Hsu 1,  Jonathan Rittichier 2,  Erkin Kuru 1,  Jacob Yablonowski 1,  Erick Pasciak 2,  Srinivas Tekkam 2,  Edward Hall 2,  Brennan Murphy 2,  Timothy K Lee 3,  Ethan C Garner 4,  Kerwyn Casey Huang 3 5,  Yves V Brun 6,  Michael S VanNieuwenhze 1 2
Affiliations

Affiliations

  • 1 Department of Molecular and Cellular Biochemistry , Indiana University , Bloomington , IN 47405 , USA . Email: [email protected].
  • 2 Department of Chemistry , Indiana University , Bloomington , IN 47405 , USA.
  • 3 Department of Bioengineering , Stanford University , Stanford , CA 94305 , USA.
  • 4 Molecular and Cellular Biology (FAS) Center for Systems Biology , Harvard University , Cambridge , Massachusetts 02138 , USA.
  • 5 Department of Microbiology and Immunology , Stanford University School of Medicine , Stanford , CA 94305 , USA.
  • 6 Department of Biology , Indiana University , Bloomington , IN 47405 , USA . Email: [email protected].
PMID: 28989665 DOI: 10.1039/c7sc01800b
Abstract

Fluorescent d-amino acids (FDAAs) enable efficient in situ labeling of peptidoglycan in diverse Bacterial species. Conducted by enzymes involved in peptidoglycan biosynthesis, FDAA labeling allows specific probing of cell wall formation/remodeling activity, Bacterial growth and cell morphology. Their broad application and high biocompatibility have made FDAAs an important and effective tool for studies of peptidoglycan synthesis and dynamics, which, in turn, has created a demand for the development of new FDAA probes. Here, we report the synthesis of new FDAAs, with emission wavelengths that span the entire visible spectrum. We also provide data to characterize their photochemical and physical properties, and we demonstrate their utility for visualizing peptidoglycan synthesis in Gram-negative and Gram-positive Bacterial species. Finally, we show the permeability of FDAAs toward the outer-membrane of Gram-negative organisms, pinpointing the probes available for effective labeling in these species. This improved FDAA toolkit will enable numerous applications for the study of peptidoglycan biosynthesis and dynamics.

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