N-Terminal speciation for native chemical ligation†
Oliver R.
Maguire, 
‡a
Jiayun
Zhu,
a
William D. G.
Brittain,
a
Steven L.
Cobb
a
and
AnnMarie C.
O’Donoghue
*a
‡a
Jiayun
Zhu,
a
William D. G.
Brittain,
a
Steven L.
Cobb
a
and
AnnMarie C.
O’Donoghue
*a
Abstract
Native chemical ligation (NCL) enables the chemical synthesis of peptides via reactions between N-terminal thiolates and C-terminal thioesters under mild, aqueous conditions at pH 7–8. Here we demonstrate quantitatively how thiol speciation at N-terminal cysteines and analogues varies significantly depending upon structure at typical pH values used in NCL.
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