Structural characterization of four prochlorosins: a novel class of lantipeptides produced by planktonic marine cyanobacteria.

Biochemistry
Weixin Tang, Wilfred A van der Donk

Abstract

Prochlorosins make up a class of secondary metabolites produced by strains of Prochlorococcus, single-cell, planktonic marine cyanobacteria. These polycyclic peptides contain lanthionine and methyllanthionine residues that result in thioether cross-links. In Prochlorococcus MIT9313, a single enzyme, ProcM, catalyzes the posttranslational modification of 29 linear peptide substrates to generate a library of highly diverse cyclic peptides. To investigate the catalytic promiscuity of ProcM, we chose four prochlorosins previously demonstrated to be produced by the organism for detailed structural characterization. Nuclear magnetic resonance studies allowed unambiguous assignment of the ring topologies, demonstrating a high degree of topological diversity. The stereochemistry of the lanthionine and methyllanthionine residues was determined by gas chromatography and mass spectrometry for seven prochlorosins. All methyllanthionines had the (2S,3S,6R) configuration, and the lanthionines had the (2S,6R) configuration, irrespective of the direction of cyclization, ring size, or ring topology. These findings indicate that most, if not all, of the rings in prochlorosins are formed enzymatically by ProcM lanthionine synthetase and not by a ...Continue Reading

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Citations

Jun 25, 2013·Journal of the American Chemical Society·Noah A Bindman, Wilfred A van der Donk
Oct 5, 2012·Chemical Communications : Chem Comm·Yanxiang ShiWilfred A van der Donk
Oct 17, 2012·Proceedings of the National Academy of Sciences of the United States of America·Qi ZhangWilfred A van der Donk
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Methods Mentioned

BETA
nuclear magnetic resonance
NMR

Software Mentioned

NMRPipe
Sparky
ProcM

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