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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 

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Selective chemical modifications of polymyxin B.

Polymyxin B (1) monohydrochloride was converted to the tetra-BOC derivatives 1b and 1c by reaction with di-tert-butyl dicarbonate. The structures of these protected intermediates were established utilizing a degradative sequence that afforded 3 and 5. A method for the deprotection 2,4-dinitrophenylamines to the free amine, utilizing a strongly basic ion-exchange resin, was developed for use in the degradative sequence. The tetra-BOC derivatives 1b and 1c were used to prepare several Polymyxin B derivatives 6-27 at the DAB1 and DAB9-gamma-amine. The antibacterial activity of these selectively functionalized derivatives is reported here.[1]

References

  1. Selective chemical modifications of polymyxin B. Weinstein, J., Afonso, A., Moss, E., Miller, G.H. Bioorg. Med. Chem. Lett. (1998) [Pubmed]
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