Stereoselective C-terminal peptide elongation from Chan-Lam-Evans reaction generated isopropenyl esters
Luuk Steemers1, Jan H van Maarseveen
1Van 't Hoff Institute for Molecular Sciences, University of Amsterdam, Science Park 904, 1098 XH Amsterdam, The Netherlands. j.h.vanmaarseveen@uva.nl.
Organic & Biomolecular Chemistry
|February 5, 2019
Abstract:
C-Terminal dipeptide isopropenyl esters were synthesised by a Cu(ii)-mediated Chan-Lam-Evans enol esterification of peptide carboxylic acids and isoprenyl boroxine. These shelf stable peptide esters could be coupled stereoselectively with a variety of amino acid and dipeptide nucleophiles in high yield and purity in the presence of pyrazole/DBU as the catalyst.
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