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N-Terminal speciation for native chemical ligation.

Oliver R Maguire1, Jiayun Zhu, William D G Brittain

  • 1Department of Chemistry, Durham University, University Science Laboratories, South Road, Durham DH1 3LE, UK. annmarie.odonoghue@durham.ac.uk.

Chemical Communications (Cambridge, England)
|May 5, 2020
PubMed
Summary

Native chemical ligation (NCL) synthesizes peptides using thiolates and thioesters. This study quantifies how cysteine thiol speciation changes with structure at NCL pH, impacting peptide synthesis.

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Area of Science:

  • Biochemistry
  • Organic Chemistry
  • Chemical Biology

Background:

  • Native chemical ligation (NCL) is a key method for peptide synthesis.
  • NCL relies on reactions between N-terminal thiolates and C-terminal thioesters.
  • The reaction proceeds under mild, aqueous conditions (pH 7-8).

Purpose of the Study:

  • To quantitatively assess thiol speciation at N-terminal cysteines and analogues.
  • To understand how structural variations influence thiol speciation.
  • To determine the impact of speciation on NCL efficiency at typical pH values.

Main Methods:

  • Utilized quantitative analytical techniques to measure thiol speciation.
  • Investigated various N-terminal cysteine analogues.
  • Performed experiments at physiologically relevant pH conditions (pH 7-8).

Main Results:

  • Demonstrated significant variations in thiol speciation based on cysteine structure.
  • Showed that thiol speciation is highly dependent on pH.
  • Identified specific structural features that enhance or reduce thiolate formation.

Conclusions:

  • Thiol speciation is a critical, yet often overlooked, factor in NCL.
  • Understanding and controlling thiol speciation is essential for optimizing peptide synthesis yields.
  • Structural modifications of N-terminal residues can be used to fine-tune NCL reactions.