Accounts of Chemical Research
Accounts of Chemical Research
5 years ago

Ribosomal Natural Products, Tailored To Fit

Ribosomal Natural Products, Tailored To Fit
Wilfred A. van der Donk, Michael A. Funk
Ribosomally synthesized and Post-translationally modified Peptides (RiPPs) take advantage of the ribosomal translation machinery to generate linear peptides that are subsequently modified with heterocycles and/or macrocycles to impose three-dimensional structure and thwart degradation by proteases. Although RiPP precursors are limited to proteinogenic amino acids, post-translational modifications (PTMs) can alter the structure of individual amino acids and thereby improve the stability and biological activity of the molecule. These “tailoring modifications” often occur on amino acid side chains—for example, hydroxylation, methylation, halogenation, prenylation, and acylation—but can also take place within the backbone, as in epimerization, or can result in capping of the N- or C-terminus. At one extreme, these modifications can be essential to the activity of the RiPP, either as a compulsory step in reaching the final molecule or by imparting chemical functionality required for biological activity. At the other extreme, tailoring PTMs may have little effect on the activity in an in vitro setting—possibly because of test conditions that do not match the biological context in which the PTMs evolved.

Publisher URL: http://dx.doi.org/10.1021/acs.accounts.7b00175

DOI: 10.1021/acs.accounts.7b00175

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