Expressed Protein Selenoester Ligation

Abstract

Scheme 1. A) Expressed protein ligation (EPL) and desulfurization. B) DSL-deselenization. C) Expressed protein selenoester ligation (EPSL) methodology.

Dissecting the role of protein phosphorylation: a chemical biology toolbox

“…This method has also been applied to generate selenoesters. 145 Blanco-Canosa and Dawson developed a diaminobenzoic acid-based linker (Dbz), 146 and later on the improved, methylated version MeDbz 147 (Fig. 12D).…”

“…Kulkarni et al 145 extended their DSL method into expressed protein ligation. To access the selenoester they modified Knorr-Pyrazole chemistry.…”

A versatileo-aminoanilide linker for native chemical ligation

“…Recently, an approach based on unprotected C-terminal peptide pyrazoles prepared from peptide hydrazides yielded the corresponding peptide–COSeR, 49 a methodology that has been further applied to a novel expressed protein–COSeR ligation. 50 Accordingly, the synthesis of C-terminal peptide–COSeR would be greatly benefited by general methods that, starting from readily available selenoester precursors, facilitate an efficient conversion under smooth conditions. Following this premise, we investigated if the peptideXaa 1 –Nbz or the peptideXaa 1 –Bt could undergo acyl exchange in the presence of benzeneselenol.…”

Synthesis of Selenoesters via Aldol Condensation and/or Conjugate Reduction and Their Antiviral Activities

“…The resulting amino acid conjugate is anticipated to be a potential antioxidant by virtue of its phenolic groups and dienyl moiety and also because similar phenolic cinnamoyl tyrosine was reported to have high antioxidant activity . Thus, unsaturated selenoesters are potentially applicable to peptide acylation such as native chemical ligation …”