6533b829fe1ef96bd12897c7

RESEARCH PRODUCT

Synthesis and Structural Stability of α-Helical Gold(I)-Metallopeptidesy

Pol BeseniusBenedict KemperLydia ZengerlingUte A. HellmichUte A. Hellmich

subject

Circular dichroismCrystallographychemistry.chemical_compoundchemistryOrganic ChemistrySupramolecular chemistrySide chainPeptide synthesisThermal stabilityLewis acids and basesBoron tribromideHEXA

description

AbstractThe synthesis of hexa- and dodecapeptides functionalized with two Au(I)–phosphine complexes is reported. The high stability of the Au(I)–phosphine bond allowed orthogonal peptide-protecting-group chemistry, even when using hard Lewis acids like boron tribromide. This enabled the preparation of an Fmoc-protected lysine derivative carrying the Au(I) complex in a side chain, which was used in standard Fmoc-based solid-phase peptide synthesis protocols. Alanine and leucine repeats in the metallododecapeptide formed α-helical secondary structures in 2,2,2-trifluoroethanol–H2O and 1,1,1,3,3,3-hexafluoroisopropanol–H2O mixtures with high thermal stability, as shown by temperature-dependent CD spectroscopy studies.

yearjournalcountryeditionlanguage
2020-10-15Synlett
https://doi.org/10.1055/a-1290-8412