Diels–Alder Ligation of Peptides and Proteins

Abstract

It is worth while, all,If the soul is not small.

Diels–Alder Cycloaddition in Protein Chemistry

“…The Diels-Alder reaction has been presented as an elegant chemoselective methodology to introduce fluorescent labels on proteins, [23][24][25][26][27][28][29][30][31] to prepare neo-glycoproteins, [32] or to chemically activated proteins. [33][34][35] Waldmann et al have applied the Diels-Alder cycloaddition as a new way to label proteins with fluorophores in vitro.…”

“…[33][34][35] Waldmann et al have applied the Diels-Alder cycloaddition as a new way to label proteins with fluorophores in vitro. [23] Streptavidin -composed of four biotin-binding subunits -was acylated with a hexadienyl bifunctional linker 1 on a lysine side chain. The diene-modified protein 2 was Scheme 2. subjected to Diels-Alder ligation with three different fluorescent labeled maleimide compounds 3, 4 and 5, in water and room temperature respectively.…”

Injectable hydrogels

“…Diels-Alder (DA) reactions have also been investigated for various biological applications due to their high yields, specific reaction (between a diene and a dienophile) that occurs in mild aqueous conditions. 226,227 No catalysts are required for the reaction and it produces no byproducts. Recently, a DA reaction-based bioconjugated HA hydrogel was characterized by Tan et al 228 Although the gels are biocompatible and degradable, the gels required over 20 min to set and reached a storage modulus under 20 Pa, which is very weak.…”

Development of fluorescent cholesterol derivatives for the exogenous introduction of proteins to the plasma membrane

“…128 Furthermore, the nonspecific conjugation of cyclooctynes to the thiols of Cys containing proteins can be significant. 152,[155][156][157][158][159][160][161][162][163][164][166][167][168][169] The inverse electron-demand Diels-Alder reaction between a strained alkene like norbornene or trans-cyclooctyne and a tetrazine is also an alternative for bioconjugations. 126,166 The tetrazine dienophile of these cycloadditions is also…”

“…[167][168][169] Furthermore, the complicated synthesis of tetrazine and trans-cyclooctyne reagents inhibits their widespread application in bioconjugations. 160,161,170 Since cholesterol can be applied as a protein membrane delivery vector, it suggests another application for introducing a bioorthogonal function to the plasma membrane of live cells.…”