N-terminal dual protein functionalization by strain-promoted alkyne–nitrone cycloaddition
作者:Rinske P. Temming、Loek Eggermont、Mark B. van Eldijk、Jan C. M. van Hest、Floris L. van Delft
DOI:10.1039/c3ob00043e
日期:——
Strain-promotedalkyne–nitrone cycloadditon (SPANC) was optimized as a versatile strategy for dual functionalization of peptides and proteins. The usefulness of the dual labeling protocol is first exemplified by the simultaneous introduction of a chloroquine and a stearyl moiety, two endosomal escape-improving functional groups, into the cell-penetrating peptide hLF (human lactoferrin). Additionally
total synthesis of himalensine A were described herein. Nitrone-induced 1,3-dipolar [3 + 2] cycloaddition was applied for the construction of A/C rings along with the all-carbon quaternary center. Pd-catalyzed enolate alkenylation and ring closing metathesis (RCM) were adopted to install the B/D rings to accomplish the [6,6,5,7] core framework. Nazarov reaction was utilized to install the F ring to complete