Construction of fluorescent analogs to follow the uptake and distribution of cobalamin (vitamin B12) in bacteria, worms, and plants

Andrew D. Lawrence, Emi Nemoto-Smith, Evelyne Deery, Joseph A. Baker, Susanne Schroeder, David G. Brown, Jennifer M. A. Tullet, Mark J. Howard, Ian R. Brown, Alison G. Smith, Helena I. Boshoff, Clifton E. Barry, Martin J. Warren

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25 Citations (Scopus)


Vitamin B12 is made by only certain prokaryotes yet is required by a number of eukaryotes such as mammals, fish, birds, worms, and Protista, including algae. There is still much to learn about how this nutrient is trafficked across the domains of life. Herein, we describe ways to make a number of different corrin analogs with fluorescent groups attached to the main tetrapyrrole-derived ring. A further range of analogs were also constructed by attaching similar fluorescent groups to the ribose ring of cobalamin, thereby generating a range of complete and incomplete corrinoids to follow uptake in bacteria, worms, and plants. By using these fluorescent derivatives we were able to demonstrate that Mycobacterium tuberculosis is able to acquire both cobyric acid and cobalamin analogs, that Caenorhabditis elegans takes up only the complete corrinoid, and that seedlings of higher plants such as Lepidium sativum are also able to transport B12. Lawrence et al., employed chemical biology approaches to construct a range of fluorescent vitamin B12 derivatives. They demonstrated that these fluorescent variants can be used to follow intracellular B12 trafficking in bacteria, including E. coli and M. tuberculosis, the worm C. elegans, and a higher plant (Lepidium sativum).

Original languageEnglish
Pages (from-to)941-951.e6
JournalCell Chemical Biology
Issue number8
Publication statusPublished - 16 Aug 2018


  • analogs
  • biosynthesis
  • Caenorhabditis elegans
  • cobalamin
  • fluorescence
  • higher plants
  • Mycobacterium tuberculosis
  • tetrapyrrole
  • trafficking
  • vitamin B12

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