Synthesis of bacillithiol and the catalytic selectivity of FosB-type fosfomycin resistance proteins.

Lamers AP, Keithly ME, Kim K, Cook PD, Stec DF, Hines KM, Sulikowski GA, Armstrong RN
Org Lett. 2012 14 (20): 5207-9

PMID: 23030527 · PMCID: PMC3544479 · DOI:10.1021/ol302327t

Bacillithiol (BSH) has been prepared on the gram scale from the inexpensive starting material, D-glucosamine hydrochloride, in 11 steps and 8-9% overall yield. The BSH was used to survey the substrate and metal-ion selectivity of FosB enzymes from four Gram-positive microorganisms associated with the deactivation of the antibiotic fosfomycin. The in vitro results indicate that the preferred thiol substrate and metal ion for the FosB from Staphylococcus aureus are BSH and Ni(II), respectively. However, the metal-ion selectivity is less distinct with FosB from Bacillus subtilis, Bacillus anthracis, or Bacillus cereus.

MeSH Terms (9)

Bacillus Biocatalysis Cysteine Fosfomycin Glucosamine Molecular Structure Proto-Oncogene Proteins c-fos Staphylococcus aureus Substrate Specificity

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