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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula.
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Facile Method for Determining Lanthipeptide Stereochemistry.

Youran Luo1, Shuyun Xu1, Autumn M Frerk1,2

  • 1Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, United States.

Analytical Chemistry
|January 17, 2024
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Summary

Researchers developed a user-friendly method using Marfey's analysis and LC-MS to determine lanthipeptide stereochemistry. This technique requires minimal peptide amounts and simplifies the characterization of these important natural products.

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Area of Science:

  • Natural Product Chemistry
  • Biochemistry
  • Analytical Chemistry

Background:

  • Lanthipeptides are ribosomally synthesized and post-translationally modified peptides (RiPPs) containing unique lanthionine and methyllanthionine cross-links.
  • Determining the stereochemistry of these cross-links is crucial for understanding lanthipeptide structure and function but is often challenging due to complex methods.
  • Existing methods for stereochemical analysis require specialized equipment, limiting their accessibility in many research settings.

Purpose of the Study:

  • To develop a facile, efficient, and user-friendly method for detecting lanthipeptide stereochemistry.
  • To establish accessible standards for key lanthionine and methyllanthionine stereoisomers.
  • To provide a scalable platform for antimicrobial discovery through improved lanthipeptide characterization.

Main Methods:

  • Utilized advanced Marfey's analysis coupled with liquid chromatography-mass spectrometry (LC-MS) for stereochemical detection.
  • Optimized LC-MS conditions for high sensitivity and minimal sample requirement.
  • Developed and described methods for synthesizing and accessing standards of lanthionine and methyllanthionine stereoisomers.

Main Results:

  • Achieved facile and efficient detection of lanthipeptide stereochemistry with a low detection limit (0.05 mg peptide).
  • Successfully characterized five (methyl)lanthionines with varying stereochemistry using a standard liquid chromatography setup.
  • Provided access to standards for three methyllanthionine and two lanthionine stereoisomers.
  • Demonstrated the utility of the method with a genome-mined lanthipeptide.

Conclusions:

  • The developed Marfey's analysis-based LC-MS workflow offers a significant advancement for lanthipeptide stereochemistry determination.
  • The method's simplicity, low sample requirement, and use of common equipment make it broadly applicable.
  • This scalable platform facilitates natural product research and accelerates the discovery of novel antimicrobial lanthipeptides.