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Download fileGeneration of Thiocillin Ring Size Variants by Prepeptide Gene Replacement and in Vivo Processing by Bacillus cereus
journal contribution
posted on 2012-06-27, 00:00 authored by Albert
A. Bowers, Michael G. Acker, Travis S. Young, Christopher T. WalshThe thiocillins from Bacillus cereus ATCC 14579
are natural products from the broader class of thiazolyl peptides.
Their biosynthesis proceeds via extensive post-translational modification
of a ribosomally encoded precursor peptide. This post-translational
tailoring involves a key step formal cycloaddition between two distal
serine residues. In the wild-type structure, this cycloaddition forms
a major macrocycle circumscribed by 26-atoms (shortest path). Results
presented herein demonstrate the promiscuity of this last step by
means of a set of “competition” experiments. Cyclization
proceeds in many cases to provide altered ring sizes, giving access
to several variant rings sizes that have not previously been observed
in nature.
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macrocyclepromiscuitygenerationBacillus cereusThe thiocillinsring sizesbiosynthesis proceedsaccessexperimentVivo Processingcycloaddition formsmodificationthiazolyl peptidesCyclization proceedsribosomallyprecursor peptideThiocillin Ring Size Variantsserine residuesPrepeptide Gene Replacementvariant rings sizesBacillus cereus ATCC 14579nature