Cu-catalyzed formation of triazole-linked glycoamino acids and application in chemoenzymatic peptide synthesis
Novel stable triazole-linked glycoamino acids have been prepared, with the heterocyclic moiety being established by efficient Cumediated cycloaddition between the corresponding azido and acetylene moieties. Selected reactions were scaled up and successful
Kuijpers, Brian H. M.,Groothuys, Stan,Hawner, Christine,Dam, Jeroen Ten,Quaedflieg, Peter J. L. M.,Sehoemaker, Hans E.,Van Delft, Floris L.,Rutjes, Floris P. J. T.
p. 503 - 511
(2013/01/03)
Chemoenzymatic synthesis of triazole-linked glycopeptides
Triazole-linked glycopeptides are prepared by C-terminal elongation of glycoamino acids with proteinogenic amino acids following a chemical or enzymatic coupling protocol. Two orthogonal routes for a chemoenzymatic strategy were explored, involving a click-reaction before amide bond formation or in reverse order. It was found that enzymatic peptide coupling under the influence of alcalase proceeds cleanly and in high yields, while the resulting dipeptides can be efficiently clicked to acetylene- or azide-containing sugars. Georg Thieme Verlag Stuttgart.
Groothuys, Stan,Kuijpers, Brian H. M.,Quaedflieg, Peter J. L. M.,Roelen, Harlof C. P. F.,Wiertz, Roel W.,Blaauw, Richard H.,Van Delft, Floris L.,Rutjes, Floris P. J. T.
p. 3146 - 3152
(2008/02/09)
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