Generation of Thiocillin
Ring Size Variants by Prepeptide
Gene Replacement and in Vivo Processing by <i>Bacillus cereus</i>
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Abstract
The thiocillins from <i>Bacillus cereus</i> 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