One-pot ligation-oxidative deselenization at selenocysteine and selenocystine

The use of native chemical ligation at selenocysteine (Sec) with peptide thioesters and additive-free selenocystine ligation with peptides bearing phenyl selenoesters, in concert with one-pot oxidative deselenization chemistry, is described. These approaches provide a simple and rapid method for acc...

Full description

Bibliographic Details
Main Authors: Payne, Richard J., Mitchell, Nicholas J., Kulkarni, Sameer S., Wang, Siyao, Malins, Lara
Format: Article
Published: Wiley 2017
Subjects:
Online Access:https://eprints.nottingham.ac.uk/39311/
Description
Summary:The use of native chemical ligation at selenocysteine (Sec) with peptide thioesters and additive-free selenocystine ligation with peptides bearing phenyl selenoesters, in concert with one-pot oxidative deselenization chemistry, is described. These approaches provide a simple and rapid method for accessing native peptides with serine in place of Sec at the ligation junction. The efficiency of both variants of the one-pot ligation-oxidative deselenization chemistry is probed through the synthesis of a MUC5AC-derived glycopeptide.