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In a dehydration reaction, a hydroxyl group in an alcohol is eliminated along with the hydrogen from an adjacent carbon. Here, the products are an alkene and a molecule of water. Dehydration of alcohols is generally achieved by heating in the presence of an acid catalyst. While the dehydration of primary alcohols requires high temperatures and acid concentrations, secondary and tertiary alcohols can lose a water molecule under relatively mild conditions.
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Microwave-assisted Functionalization of Polyethylene glycol and On-resin Peptides for Use in Chain Polymerizations and Hydrogel Formation
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Mechanistic Studies on Dehydration in Class V Lanthipeptides.

Haoqian Liang1, Isaiah J Lopez1, Marina Sánchez-Hidalgo2

  • 1Department of Biochemistry, University of Illinois at Urbana─Champaign, 600 S. Mathews Avenue, Urbana, Illinois 61801, United States.

ACS Chemical Biology
|August 31, 2022
PubMed
Summary
This summary is machine-generated.

Researchers elucidated the novel dehydration mechanism for class V lanthipeptides. An aminoglycoside phosphotransferase-like enzyme and an effector-like protein collaborate to install lanthionine residues in cacaoidin biosynthesis.

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Area of Science:

  • Biochemistry
  • Molecular Biology
  • Structural Biology

Background:

  • Lanthipeptides are ribosomally synthesized peptides with unique lanthionine (Lan) or methyllanthionine (MeLan) residues.
  • Known lanthipeptide biosynthesis involves four classes of lanthionine synthases.
  • A novel class of lanthipeptides lacks genes for these known synthases.

Purpose of the Study:

  • To investigate the biosynthesis of class V lanthipeptides, specifically the dehydration step.
  • To characterize the enzymes responsible for installing lanthionine residues in the novel class V lanthipeptide cacaoidin.

Main Methods:

  • In vitro reconstitution of the dehydration pathway for cacaoidin precursor peptide CaoA.
  • Enzyme characterization of CaoK (aminoglycoside phosphotransferase-like) and CaoY (HopA1 effector-like protein).
  • Site-directed mutagenesis and AlphaFold structure prediction to analyze enzyme-substrate interactions.

Main Results:

  • The aminoglycoside phosphotransferase-like enzyme CaoK iteratively phosphorylates Ser/Thr residues on CaoA.
  • The HopA1 effector-like protein CaoY catalyzes phosphate elimination, achieving eight successive dehydrations.
  • Mutagenesis and structural modeling highlight critical catalytic residues and hydrophobic interactions between CaoA leader peptide and CaoK.

Conclusions:

  • A novel two-enzyme system (CaoK and CaoY) is responsible for dehydration in class V lanthipeptide biosynthesis.
  • This mechanism differs significantly from previously characterized lanthionine synthases.
  • Understanding this pathway provides insights into the diversity of post-translational modifications in peptide natural products.